Your Chicago Travel Bucket List

As the third-largest city in the nation and the most centrally located, Chicago is a great travel destination. Whether you visit for a weekend, a full week, or even two, there’s no way to do everything you might want to do.

To help you make the most of your time, we’ve compiled a list of the activities visitors absolutely must do during their visit. Here are 11 things for your Chicago visit bucket list:

1. Get a Different View of the City from Willis Tower

The Skydeck at the Willis Tower offers a unique view of the city. At 1,353 feet up, the Skydeck protrudes from the side of Willis Tower on the 103rd floor and is transparent on all sides. From there, you can see more than just the city, you can actually see land in four states if it’s a clear enough day.

Source: KLM Royal Dutch Airlines

2. Hang out in Millennium Park

If you’re looking for a laid back experience with tons of Instagram-worthy spots, you have to go to Millennium Park. With the Bean (Cloud Gate), Crown Fountain, Jay Pritzker Pavilion, Lurie Garden and the adjoining Maggie Daley Park you can snap the most iconic Chicago photos.

It’s free to hang out in the park, which includes many benches to sit on and grassy areas to spread out a blanket. You can easily spend the entire afternoon there.

3. See the Largest T. Rex Skeleton at the Field Museum

The Field Museum in Chicago is home to SUE, the T. Rex. This skeleton is the largest complete T. rex specimen ever found and is named after the woman who found it, Sue Hendrickson.

This exhibit is incredible, but the Field Museum has much more to offer. Other feature exhibits include the Grainger Hall of Gems, Apsáalooke Women and Warriors, and Inside Ancient Egypt.

Source: Omaha World Herald

4. Eat at the Legendary Billy Goat Tavern

The Billy Goat Tavern opened in 1934 as a no-frills burger joint. Tavern Owner William Sianis is said to be the one who placed the billy goat curse on the Chicago Cubs in 1945.

Today, the Billy Goat Tavern is a staple in Chicago. The menu at the original tavern is pretty limited. They do just a few things and they do them really well. If you want the true Billy Goat Tavern experience, order a double cheeseburger with a bag of chips (not fries, which aren’t offered at the original location).

5. Channel Your Inner Ferris Bueller at the Art Institute

The Art Institute of Chicago, famously featured in the classic movie Ferris Beuller’s Day Off, is one of the best museums in the United States. If you want to walk in the footsteps of Ferris and his friends, be sure to see A Sunday Afternoon on the Island of La Grande.

You can also see other classics including American Gothic by Grant Wood, The Bedroom by Vincent Van Gogh, and Water Lilies by Monet.

6. Catch the Crosstown Classic

With the Cubbies on the Northside of Chicago and the White Sox on the Southside, the rivalry can get pretty intense within the city. This rivalry is at its peak at the Crosstown Classic, the in-city series where the two teams face each other.

If you only ever attend one Chicago baseball game, make it one from this series of three games. Try to catch them while they’re at Wrigley Field, a National Historic Landmark with one of the last manual scoreboards left in the nation.

7. Eat Classic Chicago Foods at the Taste of Chicago

The Taste of Chicago is a five-day food festival that features all of the best foods in Chicago and highlights businesses that started right there in the city. It is the world’s largest food festival and every foodie’s dream.

With dozens of restaurants, pop up spots, and food trucks, there’s no way you’ll be able to eat everything that catches your eye… but that doesn’t mean you shouldn’t try.

Source: Expedia Viewfinder

8. Have a Drink on a Rooftop Bar

Rooftop bars offer some of the best views of the city. You can take a seat, relax, and sip your favorite drink while you look out at the stunning skyline or the glittering water. Whether you visit during the day or at night, you’re guaranteed a picture-perfect view.

Party Slate has a helpful list if you’re looking for rooftop bars in Chicago. Do some research beforehand to find the best place in your budget.

9. See the Latest Up-and-Comers in Comedy at Second City

Second City is a Chicago improv incubator that has been the launching point for some of our favorite Saturday Night Live cast members including (most recently) Chris Farley, Tina Fey, and Steve Carrell. It’s a major point of pride in Chicago.

This year, SNL is teaming up with Second City to offer scholarships for more diverse emerging comic talent. Be sure to swing by and see performers who may be the next big names in comedy.

Source: Navy Pier

10. Ride the Ferris Wheel at Navy Pier

The Navy Pier is the Coney Island of Chicago. There are tons of shops, restaurants, and attractions. One of the most popular attractions is the Ferris Wheel. Standing 200-feet tall, riders get an incredible view of the city and of Lake Michigan.

Stick around after dark to see it light up (you might even be able to catch the firework show).

11. Engage with Wildlife at the Aquarium and Zoo

Chicago’s Shedd Aquarium and free Lincoln Park Zoo are beloved attractions within the city. You may even remember seeing the viral story about the penguins at Shedd Aquarium taking tours while the facility was closed in early 2024.

When you visit the zoo and the aquarium, you get to engage with wildlife that you might otherwise never see. In some exhibits, you can even interact with them!

Source: Wikipedia

From art to food to culture to incredible views, you really have to pack a tight schedule if you want to experience all that Chicago has to offer. When you plan your visit, start with these absolute must-do experiences to ensure you have an incredible trip.