So you just made it to Chicago, and are thinking of what to do? These are my top 5 things to do in Chicago based on my experiences. Make sure you check out our trip to Chicago here.

1. Art Institute of Chicago

The second-largest art museum in the United States, after the Metropolitan Museum of Art, the Art Institute of Chicago houses nearly 300,000 works of art. This was my highlight of my recent trip to Chicago. The place is humongous and there is so many to see. For those that have watched the movie “Ferris Bueller’s Day Off”, you can see a lot of the scenes within the movie that were filmed in the museum.

Ferris Bueller's day off at Art Institute of Chicago

I spent a whole day inside and got to see some notable works of art such as:

A Sunday on La Grande Jatte by Georges Seurat
American Gothic by Grant Wood
Self Portrait by Vincent Van Gogh

Tickets starts at $25 USD for travelers (lower prices if you are from Chicago and Illinois). I suggest purchasing tickets in advance through their website as the lines there do get long.

BONUS: Check out the public art all over Chicago! The Loop itself is a museum full of sculptures by the world’s most famous modern artists (Picasso, Calder, etc.). The best part of it, its FREE!

Flamingo by Alexander Calder at Adams and Dearborn
Flamingo by Alexander Calder at Adams and Dearborn
Chagall's Four Seasons at Monroe and Dearborn
Chagall’s Four Seasons at Monroe and Dearborn

2. Check out the Chicago Skyline

A mixture of notable skyscrapers such as Sears Tower (Willis Tower), John Hancock Center, Trump International Tower, Chicago’s world famous architecture, the Chicago River, and Lake Michigan makes Chicago have one of the more picturesque skylines in the world. There are a lot of places to check out the skyline and my favourite place is at:

The Signature Lounge Bar at the John Hancock Center

An iconic tower, The John Hancock Center, was once the tallest building in Chicago reaching 1,128 ft (343.7 m). Because it is located outside the Loop, you will get a better view of the Chicago skyline. Your view will also include the Sears Tower (Willis Tower), which you will not get if you are in the Sears Tower. Head to the Signature Lounge Bar, where you can check out the views from the 96th floor. It is FREE to enter, but you will have to purchase a drink once you are there.

skyline of Chicago from Signature Lounge

BONUS: If you’re a woman, check out the restroom, as it has an awesome view making a great bathroom experience.

3. The Second City

The Second City is an improv comedy theatre based in Chicago. It opened in 1959, and has since become one of the most influential comedy theatres in the world. Notable alumni include John Belushi, John Candy, Steve Carrel, Tina Fey, Stephen Colbert, Mike Myers, and many more.

Second City at Chicago

I have been to their shows three times (1 in Toronto, 1 in a Norwegian Cruise, and 1 in Chicago) and had a blast each time I went. If you like to laugh like me, I highly recommend going!

Tickets start around $19 USD depending on times and the show.

4. Millennium Park and Grant Park

Both public parks are major tourist attractions located within the Loop and with good reasons. Both are amazing urban parks that showcase Chicago’s smart urban design and its modern architecture. The park is also home for Chicago’s most famous attraction, “The Bean”. This attractions is a good guess as the most Instagram-ed place in Chicago.

The parks offers many other famous public art such as the:

  • Crown Fountain- a unique work of art that displays digital videos of people’s faces onto the skyscraper like fountain.
  • Buckingham Fountain – one of the largest fountains in the world with regular water shows and evening color-light shows.
  • The Pritzker Pavilion- designed by world famous Frank Gehry which hosts free concerts in the summer that visitors can enjoy.
Cloud Gate (a.k.a The Bean) at Chicago
Cloud Gate (a.k.a The Bean)
Crown Fountain
Buckingham Fountain
Pritzker Pavilion

They are also great places to walk around, people watch, and enjoy the greenery in Chicago. In the winter time, you can enjoy the ice skating rink open to the public. Millennium Park also houses the city’s annual Christmas tree.

Millennium Park's annual Christmas tree

5. Riding the Chicago “L”

More specifically riding the “L” within the Loop. The Chicago Transit Authority’s train system is known as the “L” (short for “elevated”) and serves over 700,000 people on a daily basis. The brown, pink, green, and orange lines (shown below) within the Loop are elevated. The great thing about that is the views you can get from riding these trains. You get to ride over the Chicago River, in between skyscrapers, and get to see the hustle and bustle of the city from above!

Not only is taking the L is a great way to get around Chicago, it is also a great way to see the city from another perspective. To ride the train, it only cost $2.25 USD

CTA provides a tour the ‘L’ system with these full-length videos shot from the head of a train.

This list only scratches the surface on the many things to do in Chicago. Let me know what your top 5  things to do in Chicago is!

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