(The Perfect Itinerary)

Chicago is one of those cities that has it all.  There is plenty to do and see in America's third largest city, and spending 2 days in Chicago will let you experience all of the highlights.


Millennium Park, Lakefront, Navy Pier

Cloud Gate

Millennium Park has been referred to as "the most dazzling urban park in America" and is home to some of Chicago's top attractions, including the Cloud Gate sculpture aka "the Bean."

Art Institute

One of the oldest, largest, and highly ranked art museums in the US, the Art Institute of Chicago boasts over 300,000 works in its permanent collection.

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.

Lakefront Trail

The 18.5 mile Lakefront trail borders the shore of Lake Michigan, and offers no shortage of scenic lake views throughout and is a must on your 2 days in Chicago itinerary.


Riverwalk, Magnificent Mile, Views

Architecture 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! I highly recommend the official Architecture Foundation cruise.


Known as one of the favorite things to do in Chicago among visitors and locals, the Riverwalk is a pedestrian path dotted with restaurants, cafes, art, and amazing views of the river and skyscrapers.

Magnificent Mile

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.

Navy Pier

Touristy, sure, but still worth a stop on your 2 days in Chicago itinerary. Riding the ferris wheel here is one of the most iconic things to do in Chicago.

Observation Decks

Enjoying  dazzling city views from one of Chicago's observation decks is a must on your Chicago itinerary. Check out the view from SkyDeck at Willis Tower, or 360 at the Hancock Tower!