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The Perfect 2 Days in Chicago Itinerary: What to Do, See, and Eat

Wondering all the best things to do, see, and eat in 2 days in Chicago? I’ve got ya! This 2 days in Chicago itinerary will help you experience all the best of the Windy City!

Wondering all the best things to do, see, and eat in 2 days in Chicago? I’ve got ya! This 2 days in Chicago itinerary will help you experience all the best of the Windy City!

Chicago is one of those cities that has it all: incredible architecture (it is the birthplace of the skyscraper after all), amazing food (especially that deep-dish pizza), world-class museums, beautiful green spaces, and so much more. The third-largest city in the US has all the hustle and bustle of a big city, with a Midwest charm.

There is so much to do, see, and eat in the Windy City that it’s impossible to see it all in 2 days in Chicago – but you can definitely see all the highlights that make the city so great (plus, it’s a good excuse to go back)!

Read on to help you make the most of your 2 days in Chicago and have the best trip ever!

Disclosure: This post contains affiliate links. This means that if you make a purchase or booking, I may receive a small commission at no additional cost to you.
2 days in Chicago itinerary: Chicago theatre


Chicago is famous for its cold winters, with temperatures sometimes dipping down as low as -30 F. However, there are many flight and hotels to be had during those freezing cold winter months – I’ve seen flights from San Francisco go for about $150 RT, and upscale hotels going for under $100/night. But that’s for a reason – it’s cold AF! Having lived in California all my life, I can’t even fathom how cold that is! So, unless you absolutely love the cold, I would probably not spend my 2 days in Chicago during the winter.

That said, to make up for the freezing cold winter, Chicago does tend to have beautiful summer days, and the city comes alive with various outdoor events and festivals during this time. Some of the most popular events include the Taste of Chicago, a 5 day celebration of food, and the Lollapalooza music festival, which brings many big-name music acts to the city. Summer is also a great time to spend to spend outside by the lake, which makes it an amazing time to spend 2 days in Chicago! However, it does tend to get humid in the summer, which may make your 2 days in Chicago somewhat uncomfortable.

However, those summer months are the most popular time for tourism in Chicago, so airfare and hotel rates tend to be the highest. Both of the times I’ve visited the city have been in the spring, which I’ve found to be an excellent time to spend 2 days in Chicago! Airfare and hotel rates are reasonable, and the weather was comfortable (although I’ve heard that it can still be chilly in the spring), which still made it possible to enjoy time spent outside.

Autumn is also a great time to spend 2 days in Chicago, and especially beautiful as you can see the leaves change colors, making it the perfect time to spend time in the city’s lovely parks. The air is crisp, and the temperatures get cooler, but hey, there’s no humidity and no sub-zero temps!

Also, FYI – contrary to popular belief, Chicago is not nicknamed the “Windy City” because of the wind – even though the breeze from Lake Michigan does create some wind and those tall skyscrapers create some crazy AF wind tunnels (and a bunch of people definitely saw my underwear because my skirt kept blowing up). The nickname is a reference to the hot air bellowing from some shady politicians.
2 days in Chicago itinerary: rainbow tunnels of O'hare airport


By air: For your 2 days in Chicago trip, you will most likely fly into O’hare (ORD), the city’s main airport which sits about 14 miles northwest of downtown. It is one of the busiest airports in the world, and offers nonstop flights to 228 cities in the United States and around the world.
From O’hare, you can take the CTA ‘s Blue Line into downtown Chicago. If you are staying near Michigan Avenue for your 2 days in Chicago, you can then transfer onto the Red Line. An underground pedestrian tunnel connects terminals 1, 2, and 3 to the Blue Line Station. You can also take the ATS (Airport Transit System) people mover to all terminals via terminal 2. The Blue Line runs 24 hours, with service every 6-10 minutes during peak hours, and every 30 minutes at night. A trip to city center takes about 40 minutes and costs $5.
You can also choose to fly into Midway airport, serviced primarily by Southwest along with a few other airlines. Midway is about 8 miles south of city center, and you can get to downtown in 25 minutes via the Orange Line. The station is just east of the airport terminal and requires a bit of a walk in an underground tunnel. Trains run every 6-15 minutes between 5am and 11:30pm. The cost is $2.50.
2 days in Chicago itinerary: Chicago city skyline
If you choose to rent a car for your 2 days in Chicago (you don’t need to unless you plan to leave the city), you can easily do so at either airport.
You can also choose to take a taxi or an Uber/Lyft –  A cab will run you about $35 from O’hare, and $25 from Midway; an Uber/Lyft costs about $28 from O’hare and $23 from Midway. However, Chicago is notorious for its rush hour traffic, especially around O’hare, and you should be prepared for surge pricing.
By Train: You can also decide to arrive via train for your 2 days in Chicago – the city is an Amtrak rail hub for many routes, connecting it to many destinations, both in the Midwest and as far away as Los Angeles and New York. Trains arrive and depart out of Union Station, just across the river from the Loop. There are several regional rail lines that leave out of Union Station as well.
The station is four blocks away from the Adams and Wells station on the Brown Line, otherwise you can easily take a bus downtown on lines 1, 60, 125, 151, or 156.
By Bus: Chicago has two 24-hour Greyhound bus stations that offer express service to over 20 destinations around the United States – more information here. Megabus also offers express bus service to several cities in the Midwest, including St. Lous, Milwaukee, and Minneapolis  – see here  for routes and stations.
By Car: If you choose to drive for your 2 days in Chicago, the city is connected via several major interstates and highways, including I-90 from Wisconsin, I-57 from Southern Illinois, I-94 from Detroit, and I-55 from St. Louis. The city is located 92 miles from Milwaukee, 297 miles from St. Louis, and 286 miles from Detroit.
2 days in Chicago itinerary: taking the EL (or elevated train) is the best way to get around Chicago


Downtown Chicago and Michigan Avenue, home to many of Chicago’s points of interest, are easily explored by foot. However, Chicago is a giant city and just relying on your own two feet won’t get you very far!
Luckily, Chicago has a great public transportation system (the second largest in the United States), and is laid out in a very organized fashion, making it easy to navigate during your 2 days in Chicago. The city is laid out in a grid pattern, with Madison Street dividing the city north and south, while State Street dividing it east and west. The downtown intersection of Madison and State is the starting point of this grid and addresses are relative to the distance from this point, with eight blocks to every mile.
The CTA (Chicago Transit Authority) operates an extensive train line, named the “L” because much of the trackway is elevated. The L is almost a tourist attraction in itself, since the elevated trackway will give you a different perspective of the city, especially in the Loop area (and create some awesome photo ops!).  Two of the L lines – the Blue Line and Red Line – operate 24 hours a day. The CTA also operates 128 bus lines. Between these, you can get to almost anywhere you need to go for your 2 days in Chicago.
Fares are $2.25 per ride regardless of distance, and you can transfer onto a bus or another L route for an additional 25 cents. You can also choose to get a visitor’s pass for unlimited rides; a 1-day pass costs $10, a 3-day pass is $20, and a 7-day pass is $28. This is the most convenient option if you plan to use a lot of public transit during your 2 days in Chicago.
Cash fares are allowed on buses. For the El, you must pay your fare or load your pass onto a reloadable Ventra card, or a single-use Ventra ticket. You can use the single-use Ventra Ticket to purchase a single fare or a 1-day pass, but you must load the 3-day and 7-day passes onto a Ventra Card. A Ventra Card costs $5, but the value is returned to you when you return the card. If you think you will make a return visit to Chicago, you can also register your card online to retain the $5 as a credit.
You can purchase tickets or a Ventra card and add funds to it at a ticket machine at any L station, online, via Ventra app, or at participating retail locations, such as Walgreens. See the CTA website for more information.
2 days in Chicago itinerary: Taking the El (or elevated train) is the best way to get around Chicago
Chicago is also served by rideshare apps such as Uber and Lyft, which make it another convenient way to get around, especially late at night. You can also take a taxi, especially from many hotels and points of interests in and around downtown.
You may also choose to bike during your 2 days in Chicago, especially if you find yourself there during the warmer months. The city has over 26 miles of biking and walking trails! Chicago has its own bike share service called Divvy, and you can rent a bike for an entire day for $15 (or $3 per 30 minutes). More information here.
While you can also choose to drive during your 2 days in Chicago, having a car is really not necessary. In fact, driving can be a hassle, since parking is at a premium and rates are pretty expensive.
2 days in Chicago itinerary: Chicago city skyline


Comfortable shoes or boots: You will do a lot of walking on your 2 days in Chicago, so wearing comfortable shoes is a must! Definitely get a pair of flats like these or these – they are stylish but won’t slow you down as you explore the city!
In the winter, you’ll want boots that keep you warm and dry. These boots and these boots are stylish and waterproof and will help your stay comfy even when walking around the city all day. You may also want to consider a pair of insulated snow boots to beat the freezing cold.
A power bank + adapter: You’ll want to stay connected during your 2 days in Chicago, and a good power bank will help ensure that your phone never runs out of juice! This power bank is a MUST on every single trip that I take – both in the US and internationally! If you’re from abroad, you may also need a power adapter to charge your devices – I always travel with this one.
Reusable water bottle: Staying hydrated as you explore the city on your 2 days in Chicago is essential! Be nice to the environment and avoid buying plastic bottles of water and carry a reusable water bottle – this is the one I carry with me at all times. I love that it is screw top but has a spot so it’s easy to take quick sips without spilling all over yourself, and holds enough water to help you stay hydrated all day.
2 days in Chicago itinerary: endless views of the Chicago city skyline


Chicago sometimes gets a bad rap as being a rough city, but I found it to be relatively safe, even as a solo female traveler. That is not to say that crime can happen during your 2 days in Chicago – like any major city, Chicago has some dangerous neighborhoods, mostly in the South Side (save for Hyde Park), that you definitely should not venture into.
As always, you should always use precaution and always stay aware of your surroundings. Listen to your gut – if it is telling you that something is off, then it probably is! Don’t stay out alone late at night (if you do, take an Uber/Lyft instead of walking alone), and don’t get super drunk while alone. Keep a close eye on your belongings – petty crime is very common in tourist hotspots, so always keep a close watch during your 2 days in Chicago!
2 days in Chicago itinerary: view of the Chicago river and skyline


Short answer – no – there is soooooo much to do and see in the city that 2 days in Chicago won’t even come close to enough to see it all! However, I have found that 2 days in Chicago is definitely more than enough time to see all the highlights and to get a good introduction to the city. It will definitely leave you wanting to come back!
2 days in Chicago itinerary: Chicago city skyline


Many of Chicago’s hotels are located in the downtown Loop area, making it an easy walk to many of the city’s main tourist attractions, such as Millennium Park, the Riverwalk, and the Lakefront trail. There are also many hotels located along the Magnificent Mile area near Michigan Avenue, which is an easy walk from the Loop. Staying in either of these areas would be convenient for your 2 days in Chicago.
I stayed at the Wit, located in the Loop area, right in the heart of all the action. It was definitely the perfect location for my 2 days in Chicago, and it was convenient to walk to many of the places that were on my to-do list – and the L stopped right nearby so I could easily hop on it to get to all the places I couldn’t walk to. The convenient location definitely helped me do and see as much as possible during my 2 days in Chicago!
The hotel also has a hip, colorful, modern boutique hotel vibe. The property is actually a Doubletree Hotel, so you get all the comforts of staying in one (and you will get allll the chocolate chip cookies you want during your 2 days in Chicago, which is always a plus in my book!) but it has a trendy vibe which makes you think you’re staying in a hip boutique hotel. The hotel also has a rooftop bar, which has been recently remodeled and is a super fun spot to hang out at!
Other properties you may consider, depending on your budget and tastes:
The Freehand Chicago: Aside from the fact that it is conveniently located in the Magnificent Mile, the best part about the Freehand is that it has rooms to suit any budget – shared dormitory-style rooms, private rooms, and penthouses, making it an excellent place to stay for your 2 days in Chicago! The property is also hip, trendy, and stylish, and also has an award-winning cocktail bar, the Broken Shaker, on site!
Virgin Hotels Chicago: You definitely can’t beat the location of the Virgin Hotel, in the heart of the Loop and an excellent place to stay for your 2 days in Chicago! The Virgin Hotel combines comfort with modern amenities, and has common spaces for socializing, along with a hip rooftop bar offering panoramic views of the city.
Conrad Chicago: If you want a taste of luxury with a bit of style during your 2 days in Chicago, the Conrad makes an excellent choice. You can’t go wrong with the location as well, on the northern end of the Magnificent Mile. You’ll be pampered in style at the Conrad, and you also can’t beat the rooftop here, which offers panoramic views of the city.
Find more amazing places to stay in Chicago and compare the best rates here.
2 days in Chicago itinerary: gardens of Millenium park


Millennium Park
Located in the heart of Chicago in the Loop, Millennium Park is a 24-acre urban park that is home to several of the city’s top attractions and therefore is a must during your 2 days in Chicago. The park is relatively new to Chicago – it opened in 2004 – but it gave new life to the city, as it replaced some unsightly railroad tracks and parking lots in the area. Today, Millennium Park has been called “American’s most dazzling urban park” and recently replaced Navy Pier as the top tourist attraction in the Midwest.
It is a gathering place for both locals and tourists alike, and you definitely need to make a stop during your 2 days in Chicago to take in all the greenery and gardens, fountains, and public art pieces inside the park. The main attraction here is the Cloud Gate sculpture, aka “the Bean” (which I will talk about in a second), but there is much more to the park than just that!
Be sure to walk across the Frank Gehry-designed BP Bridge, from which you can take in some amazing views of the city’s skyline. The pedestrian bridge leads into the Jay Pritzker Pavilion, which regularly hosts outdoor concerts and festivals. Even if you don’t catch an event here during your 2 days in Chicago, the pavilion is worth a look, as it rises 120 feet tall and features metal structures that evoke ribbons blowing in the wind.
Also check out the Crown Fountain, which pays a unique tribute to the people of Chicago. Inspired by the historic fountains that have gargoyles with water spewing out of their mouths, this version features two 50 foot tall glass towers with LED screens that display rotating images of 1000 of Chicago’s residents.
Other things to do inside Millennium Park during your 2 days in Chicago include checking out the public art installations inside the Chase Promenades, enjoying a moment of serenity at the Lurie Garden, and rock climbing at Maggie Daley Park, right across the pedestrian bridge.
2 days in Chicago itinerary: Cloud Gate aka The Bean
Cloud Gate, aka “The Bean”
If you didn’t go to the Bean, did you even go to Chicago? Ok, but the Bean may just be Chicago’s most popular landmark, so it would be criminal to not pay it a visit on your 2 days in Chicago. The Bean is actually officially called “Cloud Gate,” and was created by an Indian-born British artist named Anish Kapoor. It is made up of 168 stainless steel plates which were welded together and polished so that there were no visible seams. It gets its nickname from its iconic kidney bean-like shape.
2 days in Chicago itinerary: Cloud Gate aka the Bean
The sculpture was inspired by liquid mercury, and the coolest thing about it is definitely seeing the unique reflections you get of the city’s skyline and the activity in Millennium Park. Be sure to spend some time walking around the giant sculpture to check out your own reflection on it – it’s pretty cool to see how it changes and it really makes for some cool photo ops!
2 days in Chicago itinerary: Cloud Gate aka the Bean
The area around the Bean is always swarming with people at most hours during the day. If you want to admire the sculpture with a bit of peace of quiet and for the best photo ops, I suggest coming early in the morning. I rolled out of bed at 6 am and walked over to the Bean to snap this photo (and promptly went back to my hotel to take a nap afterwards), and a small crowd was already forming as I was leaving. By the time I walked past it later in the afternoon, the place was a madhouse!
2 days in Chicago itinerary: The Art Institute of Chicago
With more than 300,000 works in its permanent collection, the Art Institute of Chicago is one of the largest, oldest, and most highly ranked art museums in the United States, making it a must visit spot during your 2 days in Chicago.
The collection features works created over a span of over 5000 years, and boasts the largest collection of Impressionist and post-Impressionist paintings outside of the Louvre Paris. However, the museum houses an impressive collection of masterpieces from all around the world, including ancient Greece and Japanese prints. Notable artists with artworks on display at the Art Institute include Monet, Picasso, Van Gogh, Matisse, Chagall, Pollock, Renoir, and many, many more!
The museum spans almost 1 million square feet, so there is no way that you’ll see it all in one visit, especially when you only have 2 days in Chicago. You can literally spend an entire day here and still not cover it all! Luckily for you, you can still see the highlights in a short period of time – the museum even provides a “what to see if you only have an hour” guide that will tell you what masterpieces you must see, and where they are so you can quickly get to them instead of aimlessly wandering the museum to try to find them! I definitely found this helpful and it was a life-saver to make the most of my visit even though I was pressed for time. You can also download the museum’s mobile app, which includes several guided audio tours and commentary.
Some of the museum’s most famous works that you absolutely must see include Grant Wood’s iconic “American Gothic,” Marc Chagall’s stained glass windows, Andy Warhol’s pop-art portrait of Elizabeth Taylor, Hokusai’s famous wood block painting depicting a wave, Monet’s Water Lilies and Stacks of Wheat paintings, and George Seurat’s “A Sunday on La Grande Jatte,” which was also featured in “Ferris Bueuller’s Day Off.’
2 days in Chicago itinerary: Buckingham Fountain against the Chicago city skyline
Buckingham Fountain
Not only is the Buckingham Fountain one of Chicago’s most famous landmarks – you may recognize it from the opening credits of Married With Children – it is also one of the largest fountains in the world! You should make a stop to admire the impressive fountain during your 2 days in Chicago.
Built in 1927, Buckingham Fountain was inspired by the Laton Fountain at the Palace of Versailles. The fountain is an impressive 280 feet in diameter and has three basins with four Art Deco-style seahorses that represent each of the states that border Lake Michigan – Illinois, Indiana, Michigan, and Wisconsin. The size of the fountain is said to symbolize the enormity of the lake, and uses some 15,000 gallons of water per minute.
2 days in Chicago itinerary: Buckingham Fountain
The fountain runs from 8am to 11pm while it is in operation from early May to mid-October. There is a 20-minute display that starts at 9am and runs every hour, on the hour throughout the day. At night, lights and music also accompany the display, and ends with a climax that shoots water over 150 feet in the air – it is quite an impressive sight in front of the backdrop of the Chicago skyline!
2 days in Chicago itinerary: Skydeck at the Willits Tower
You will definitely feel like you’re on top of the world as you look out into the city and beyond (on a clear day, you can see a view of four states) from the 103rd floor of the Willits Tower, aka the second tallest building in the Western Hemisphere. People always ask Skydeck is worth its admission price, and the answer is a resounding YES – It will definitely be one of the highlights of your 2 days in Chicago!
The highlight at Skydeck is the Ledge, the platform with a glass floor that juts out from the edge of the Willits Tower, giving you an unparalleled view of the city – from 1353 feet above ground! It’s definitely a cool experience and one you should definitely check out during your 2 days in Chicago!
2 days in Chicago itinerary: Skydeck at the WIllits Tower
If you’re afraid of heights, then you might be a bit shaky at the idea of walking out onto the Ledge, but I say doooo it! It’s an amazing way to experience the city’s skyline and an experience like no other. Plus, trust me, that glass is reinforced like crazy and there is no way that thing is going to crack – I even jumped on it and it did not budge AT ALL. I actually wasn’t scared when I was actually on the Ledge, but then freaked a bit when the docent pointed it out on the architecture cruise the next day – like holy $*#(&$, it’s really, REALLY high up there (I mean, obvi)!
Plus, you will get some amazing photos here to commemorate your 2 days in Chicago! You should definitely snap a photo of your feet with the city below you, and sitting and/or lying down on the glass will also make for a cool shot. Another fun photo would be to have a friend stand in one of the windows across from you and take a shot of you in your own box. This is, of course, best done when Skydeck is not crowded, like when in the morning when it first opens.
In my opinion, the best time to visit Skydeck is during the 30 minutes or so before the sunset. Not only is it a super awesome place to watch the sunset, you can watch as the sky transforms from light to dark, and you can start to see the skyline come alive as the lights come on. I think those city lights during blue hour (that bit of time right after the sun sets and the sky turns blue) make for the BEST photos because you get those twinkly lights but it’s much easier to snap those photos as it is when the sky is completely dark. I always think that the best time to visit any observation deck type attraction is around sunset for that very reason!
2 days in Chicago itinerary: Skydeck at the Willits Tower
Skydeck also offers a day/night admission ticket that allows you to visit once during daylight hours, and to return again at night. Coming around sunset is my hack to get the same experience but save some money because you only have to pay for one visit! However, if you really want to come during two separate visits, I would suggest getting the Chicago City Pass, as this included a day/night ticket, along with priority admission to lots of other attractions in the city – a great way to save money during your 2 days in Chicago!
Just know that everyone else will want to watch the sunset from Skydeck and it will be crowded AF around that time – you will most likely have to wait an hour in line before you make it up to the top, so be sure you leave plenty of time for this and don’t miss the sunset! If you’re short on time (because let’s face it, 2 days in Chicago is a very short amount of time), you can also purchase a skip the line pass that gives you access to an express elevator, but at $75 it is a very pricey and I don’t know if that is worth it.
2 days in Chicago itinerary: Skydeck at the Willits Tower
I’ve also found that going to Skydeck first thing in the morning, right at opening, is another good time to go. While you won’t get those twinkly lights in your photos, you’ll still get some amazing shots because, well, there won’t really be anyone photo-bombing you. It’s definitely a much more pleasant experience when you’re not fighting 493583059830495 people who are also trying to get the same shot as you! You’ll avoid the extra long wait in line to go up the elevator as well, which is a plus when you’re trying to maximize your time on your 2 days in Chicago.
2 days in Chicago itinerary: Chicago skyline from the Architecture Foundation River Cruise
Chicago is a city known for its architecture, and the best way to take it in is to see it from a boat while cruising down the river! It is definitely a relaxing activity that helps you rest your feet for a little bit from all that exploring in your 2 days in Chicago.
There are many companies that offer architecture cruises, but please do yourself a favor and do the one from the Chicago Architecture Foundation! It is a little bit more expensive than the others, but the tours are conducted by volunteer docents, who are doing it for their love of architecture than the money. They are very well-informed, enthusiastic, and entertaining, and their passion for both architecture the city of Chicago definitely comes through during their narration on the tour!
On your 90 minute cruise, you will learn a lot about the history of architecture and the history of Chicago, hear fascinating stories behind 50 notable buildings throughout the city (and of the architects who built them), and get a crash course on all the different historic and modern styles of architecture. There are also plenty of photo ops, and the docents will point out where to get all those Instagrammable shots of the Chicago skyline!
2 days in Chicago itinerary: view of Willits Tower from Chicago Architecture Foundation River Cruise
If you want a different perspective of the Chicago skyline and see the lights twinkle against the night sky, you may also want to consider a twilight tour, which are available from mid-May until mid-October.
You can do all this while you sit back and relax with a beverage (glass of white wine for me, thanks) in hand. You will feel like you’ve seen so much of the city, but all you’re doing is sitting on a boat and soaking up the views and information! This was definitely a highlight of my first trip to Chicago, so much that I did it again on my second trip to the Windy City – definitely a must-do activity during your 2 days in Chicago!
2 days in Chicago itinerary: Chicago Riverwalk
Chicago Riverwalk
The Chicago Riverwalk is a 1.25 pedestrian trail along the south bank of the Chicago River, spanning from Lake Shore Drive to Lake Street. It may be highly touristy, but it’s a favorite spot for locals as well, making it one of the musts for your 2 days in Chicago.
There are many restaurants, cafes, bars, monuments, public art pieces, and even a museum along the Riverwalk. You can even rent a kayak from one of the docks there. You can choose to spend just 30 minutes here – or an entire afternoon! My favorite way to experience the Riverwalk is to stroll through the entire span, stopping every so often in one of the sitting areas to people watch and take in the views – did I mention that the Riverwalk also has excellent photo ops of the skyline and river? You can also do some relaxing and doing some people watching at one of the cafes or bars along the Riverwalk.
2 days in Chicago itinerary: Bridges of Chicago from Riverwalk
You should definitely spend some time watching the boats go by, and admire all the bridges along the river. Be sure to wait to see a bridge lift to let a boat pass through – one of the coolest sights on the Riverwalk! For the full experience, you can also stop by the McCormick’s Bridgehouse and Chicago River Museum, from where you’ll see all the gears that lift the bridge in action. You can also climb to the top of the tower for some excellent views of the city as well!
2 days in Chicago itinerary: view of skyline from Lakefront Trail
Lakefront Trail
The 18.5 mile Lakefront trail borders the shore of Lake Michigan, and offers no shortage of scenic lake views throughout. The trail is open year round, 24 hours a day, which makes it a perfect activity mon our 2 days in Chicago, no matter what time of the year you visit.
There are many ways to experience the Lakefront Trail, based on your personal interests, and how much time you want to spend here – you can walk, go for a run, rent a bike, even roller blade along the trail. It doesn’t matter how you choose to explore the trail, just make sure you experience at least part of it on your 2 days in Chicago!
2 days in Chicago itinerary: view of skyline from Lakefront trail
Most visitors will choose to walk part of the trail, and the stretch that borders Grant Park is a great stretch to explore on your 2 days in Chicago. From here, you will not only enjoy scenic views of the lake, but also dramatic views of the city’s skyline – you will definitely make plenty of stops in order to snap a bunch of photos!
If you want to fit in a workout on your 2 days in Chicago – hey, all that deep dish pizza isn’t going to work itself off – the trail offers a flat, easy, paved running or biking route and you can make your run as short or as long as you like. The trail also has designated bike lanes which will help avoid chaos and near-collisions. An easy, affordable way to rent a bike is through Divvy, the city’s bike share program, which offers bikes for $3 an hour, or $15 for an entire day. You can see more information about this here.
During the summer months, you’ll find plenty of sunbathers along the trail. There are several beaches along the Lakefront Trail where you can lay out in the sun. Some of the best and most accessible include Oak Street Beach, which has incredible views of the city; the 57th Beach, right next to the Museum of Science and Industry; and the North Street Beach, right next to the Lincoln Park Zoo.
2 days in Chicago itinerary: Michigan Avenue aka the Magnificent Mile
Magnificent Mile
If you’re looking for some retail therapy during your 2 days in Chicago, this is the perfect place to do it! The area along North Michigan Avenue is known as the Magnificent Mile, and it is known as one of the premier shopping districts in the world. Hundreds of retailers – from giant shopping malls, popular department stores, luxury designer stores, and trendy boutiques – line the strip, offering a shopaholic’s paradise!
Not much of a shopper? The Magnificent Mile is still worth walking through on your 2 days in Chicago, as you will be surrounded by many of the city’s tallest skyscrapers. There are several noteworthy buildings that line the Magnificent Mile, including the 100-story John Hancock Tower (more on that later), the Wrigley Building, the Tribune Tower, and Water Tower, which is one of the only buildings in the city to survive the Great Chicago Tower (it’s houses a bustling shopping mall these days).
Are you spending 2 days in Chicago during the winter months? The Magnificent Mile comes alive during the holiday season. Not only do many of the retailers come up with some spectacular storefront displays, the avenue comes alive as it is illuminated with over one million holiday lights!
2 days in Chicago itinerary: view from Hancock Tower
John Hancock Tower
Chicago has no shortage of giant skyscrapers, and you can’t go wrong with a view of the city from the top of a super tall building. Another place to get a bird’s eye view of the city during your 2 days in Chicago is at the John Hancock Tower. You can visit 360, the observation deck on the 94th floor to experience those breathtaking panoramic city views. Thrill seekers may also choose to go on Tilt, a ride with an enclosed glass and steel platform that tilts outwards over 1000 feet above the Magnificent Mile, giving you a unique, downward facing window overlooking the city!
However, these observation decks are pricey and the costs can add up over your 2 days in Chicago. Instead of paying to go up to 360 (unless you have a Chicago City Pass, since 360 is included), I suggest that you go up to Signature Lounge, the revolving bar on the 95th floor.
2 days in Chicago itinerary: view from Signature Lounge in the Hancock Tower
Sure, grabbing a drink here is also expensive (and may cost almost as much as paying for admission for 360), but you can soak in those panoramic city views while relaxing with a cocktail in hand, which is also a great way to rest your feet after all the walk you’ve done on your 2 days in Chicago. Also, pro tip: the best view in the house is from the ladies’ restroom (sorry gents). Seems kinda random, but it’s true – you’ll even see people lined up there to get their photo op!
2 days in Chicago itinerary: Navy Pier ferris wheel
Navy Pier
Only if you must – there are much more interesting places to go during your 2 days in Chicago! Navy Pier is touristy AF, but it’s also one of the most popular tourist attractions both in the city and the Midwest (it used to be the most popular attraction in the Midwest until Millenium Park overtook it in 2018). Honestly though, Navy Pier is to Chicago as Fisherman’s Wharf is to San Francisco – full of cheesy souvenir shops, overpriced yet mediocre restaurants, and lots of crowds.
However, what Navy Pier has that Fisherman’s Wharf does not is an iconic 200-foot tall ferris wheel, and well, I’m kinda a sucker for ferris wheels (which is how I ended up at Navy Pier). Gotta admit, the views from the top were kinda sweet. So, Navy Pier is worth a stop on your 2 days in Chicago if you really like ferris wheels – otherwise, skip.
2 days in Chicago itinerary: Wrigley Field
Attend a Cubs Game at Wrigley Field
If you find yourself spending 2 days in Chicago during baseball season, check out the Cubs’ schedule to see if they are playing at home at Wrigley Field. If they are, definitely get yourself out to the ballgame!
Wrigley Field, which opened in 1914, is currently the second oldest stadium in Major League Baseball. The stadium is characterized by its signature 81-year old ivy vines on the outfield wall, and its manually operated scoreboard. They just don’t make stadiums like this anymore, and it’s super cool to take a step back into baseball history. Plus, Chicagoans are passionate AF about their sports team (especially their beloved Cubs), and it’s kinda fun to hang out with them. And going to a ballgame is the perfect way to spend a balmy summer evening!
If the Cubs aren’t playing during your 2 days in Chicago, or you really want an in-depth look at the history behind Wrigley Field, they do also offer guided tours on the weekends in October.
2 days in Chicago itinerary: Chicago Theater
Watch a Comedy Show at Second City
Want to see the next big names in comedy perform during your 2 days in Chicago? Many of comedy’s big names once performed at the historic comedy club and academy, which has been in Chicago since 1959. Both Tina Fey and Amy Poehler, who spent some time as part of the cast at Second City, wrote about there time here in their memoirs (which piqued my interest!), but some of Second City’s other famous alums include Joan Rivers, Steve Carrell, Stephen Colbert, Chris Farley, Bill Murray, and many, many more notable comedians.
Second City puts on several shows nightly, showcasing their headliners, improv troupe, guest performers, and comedy students. You just might be able to see the next big thing in comedy perform! You can see the performance calendar and buy tickets here.
2 days in Chicago itinerary: view of bridges on the Chicago River


Wondering how exactly to spend your 2 days in Chicago? Follow the below itinerary and you’ll be guaranteed to experience the best of Chicago in 2 days! It will be jam-packed and you will be on the go all the time, but I promise you, it will be worth it!
2 Days in Chicago Itinerary – Day 1:
– Start your day off in Millenium Park. Go say hi to the Bean first thing in the morning to beat all the crazy crowds.
– Walk across the BP pedestrian bridge, and check out the Jay Pritzker Pavilion and Crown Fountain, and enjoy a moment of serenity at the Lurie Garden.
– Spend a couple hours at the Art Institute. Since you only have 2 days in Chicago, you won’t have a whole lot of time, so make the most of it! Start with the museum’s “what to see if you only have an hour” guide, and then seek out a few other notable pieces that you want to see!
– Walk through Grant Park, and snap some photos of the grand Buckingham Fountain against the Chicago skyline.
– Head towards Lake Michigan and stroll along the Lakefront Trail.
– Stop at Navy Pier to ride the ferris wheel – if you must!
– Spend a summer evening catching a ballgame at Wrigley Field.
2 Days in Chicago Itinerary – Day 2:
– Relax on the river and learn about Chicago’s history and architecture on the Architecture Foundation’s river cruise.
– Stroll down the Chicago Riverwalk, checking out the views of the river, bridges, and skyline.
– Go to the Hancock Tower and head up to 360, the observation deck; OR, relax and soak up the views with an afternoon beverage at the Signature Lounge on the 95th floor (my choice).
– Walk through the Magnificent Mile, admiring the architecture and getting your retail therapy on.
– Go to Skydeck at the Willits Tower to watch the sunset and watch Chicago’s skyline transform as the city’s lights come alive.
– End the evening with a comedy performance at Second City
2 days in Chicago itinerary: deep dish pizza


Where Should I Eat Deep Dish Pizza?
You can’t go to Chicago and not try the city’s most famous food item, the deep dish pizza. The question is – where? With so many restaurants serving deep dish pizza (and claiming that they have the best), and with so many people having a (very strong) opinion about what their favorite is, it can be hard to decide where exactly to go on your 2 days in Chicago.
Luckily for you, I’ve sampled lots of deep dish pizza during my time in Chicago! Here are my top 3 picks for where you should eat deep dish pizza during your 2 days in Chicago:
Giordano’s: Giordano’s serves up a solid deep dish, and has the perk of having multiple locations that are close to some popular attractions, such as Millenium Park, the Magnificent Mile, and Navy Pier, so it’s an excellent choice if you are pressed for time but want to get a pizza fix (which you probably will be seeing as you only have 2 days in Chicago). Their specialty is the Chicago Classic Deep Dish, which has everything you need from a deep dish pizza – a crisp, flaky crust, fresh tomato sauce, plenty of cheese, and tons of toppings!
Lou Malnati’s: Lou Malnati’s is a crowd favorite of both tourists and locals alike, and it’s easy to see why – the deep dish here is simple yet authentic, and definitely satisfying. The buttery crust here is a trademark (like, literally trademarked), and you won’t get enough! Lou Malnati started as one single location in 1971, but has since expanded to over 50 locations so chances are you’ll find one that is convenient to you! If you’re pressed for time, they also offer pizza to go as well.
Pequod’s: This might have been my favorite on my last 2 days in Chicago trip! Pequod’s has long been a favorite of locals, and since it still only has 2 locations, it still has that neighborhood pizza joint vibe. And the deep dish is to die for! What sets Pequod’s apart is the signature “halo,” which is created by sprinkling cheese edge to edge to create a crisp, brown rim on the outside. Soooo good!
2 days in Chicago itinerary: Girl and the Goat
I had so many friends recommend Girl & The Goat before my 2 days in Chicago, and it definitely did not disappoint! Girl & The Goat is helmed by Stephanie Izard, aka the first female winner of Top Chef, and is ranked as one of the 50 best restaurants in the world. They offer up inventive small plates with a global spin, that are bold but not tooooo out there. Think squash blossom crab rangoons with chive yogurt, soft shell bap xao (Vietnamese style corn) with gochujang (Korean chili sauce) mayo, and duck tongue with tuna and black bean poke. The flavor combinations are fun and just WORK, and the restaurant itself has a “rustic but badass” vibe (in the chef’s own words). Seriously, do yourself a favor and have a meal here during your 2 days in Chicago! Just know that it is one of the most popular restaurants in Chicago – for good reason – so plan ahead! Be sure to make a reservation in advance, but if you can’t get one, try to get a walk-in table at 4:30pm on the dot, when the restaurant opens.
2 days in Chicago itinerary: Little Goat
Couldn’t snag a reservation to Girl & The Goat, or want something a little bit more casual? Little Goat is the Girl & The Goat’s creative take on a diner, and is a fun spot for a delicious brunch during your 2 days in Chicago (they also have a lunch and dinner menu as well)! Little Goat puts a unique spin on classic comfort dishes from the US and around the world, like shrimp and cheesy grits with braised pistachio; bi bim bop with cauliflower rice, pickled veggies, and a fried egg; or a bull’s eye French toast, with crispy chicken, BBQ maple syrup, and a poached egg inside the sweet onion brioche bread. My favorite thing here was the okonomiyaki, which is one of my absolute favorite Japanese comfort foods (it’s essentially a Japanese pancake – and I tell my mom to make it for me every single time I go home). Little Goat’s version is made with pork belly and is to die for!
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#AuCheval #Hogsalt

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Au Cheval’s famous burger has received many, many accolades, including being declared one of the best, if not THE BEST burger in America. So obviously, it is also one of Chicago’s most popular restaurants, and people wait up to three hours for a taste of that burger. Is it worth it? Absolutely yes, and a must eat during your 2 days in Chicago – maybe not THE BEST burger I’ve ever had, but it is definitely one of my top 5! Should you wait three hours for it? Absolutely not! Au Cheval is open until 1am, and the best time to come is late at night after 10pm (second dinner, anyone?), at which time the wait is no more than 20 minutes.
Au Cheval’s burgers are perfectly juicy, and that juice will dribble down your arm as you take one irresistible bite after another. Just know that the burgers are HUGE – a single comes with two patties, a double comes with three. Definitely add a fried egg on top!
2 days in Chicago itinerary: Portillo's all beef Chicago Dog
It would be a shame to spend 2 days in Chicago and not eat a Chicago dog and Portillo’s is the place to grab one! The chain has been a Chicago mainstay for over 50 years, and serves up the juiciest, most flavored packed hot dog you’ll find on your 2 days in Chicago. Portillo’s started with humble beginnings back in 1963, when it started in a tiny trailer as “The Dog House,” but has since expanded to over 50 locations, most of which are in the Chicago area – so you’ll definitely be able to find one convenient to you during your 2 days in Chicago. Be sure to try the Jumbo Beef Dog, and get a side of cheese fries with it! Another plus – it’s cheap!



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Avec serves up delicious Mediterranean cuisine in a communal setting – you’ll most likely end up making some new friends! Avec wasn’t on my list during my last 2 days in Chicago trip, but we stumbled upon it one night and it definitely did not disappoint. The menu is always evolving, but there are a few mainstays, one of which is the bacon wrapped dates (stuffed with chorizo), which you absolutely must order. They come with a decadent sauce that you can scoop up with the delicious focaccia, another menu classic. They also have a well-curated wine list (Avec was originally intended to be a wine bar), with lots of great Mediterranean wines. I’m not all too familiar with wines from this region, but the staff is always happy to make a recommendation, so definitely try a glass of something new! Avec doesn’t take reservations, and you’ll probably have to wait a bit – the CH Distillery down the street has excellent cocktails and is a great spot to kill time. Otherwise, I’ve heard that there is no wait at lunch.
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Have you been spent 2 days in Chicago? What are your favorite things to do, see, and eat there? Throw them out in the comments below!
Wondering all the best things to do, see, and eat in 2 days in Chicago? I’ve got ya! This 2 days in Chicago itinerary will help you experience all the best of the Windy City!
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