Chicago Bucket List (2025)

This Chicago bucket list covers the best attractions in Chicago, awesome restaurants and hidden gems we discovered whilst living there.

Chicago offers a variety of attractions to suit the whole family, as well as being a romantic and relaxing place for couples. Strolling through the neighborhoods and visiting Chicago’s great bars and restaurants is one of the best ways you can spend your time in Chicago but for those who wish to explore more, this is our top 10 things to do in Chicago.

The Chicago Pass can help you save quite a bit of money if you are planning on visiting all the top attractions during your stay.

Chicago Bucket List

1. Grant Park

A tranquil and relaxing attraction with various sculptures and architecture dotted across the park. The park is open from 6 am to 11 pm and is located between Michigan Avenue and Lake Michigan. It is home to many famous landmarks including the Buckingham Fountains and Lincoln Statue.

2. Navy Pier

Perfect for a few evening drinks and dinner, head to Navy Pier for a choice of many restaurants and eateries as well as a great view of the Chicago skyline and a few rides and attractions.

3. Cloud Gate

Found in Grant Park, the Cloud Gate is a popular and famous landmark of Chicago, making it have its own spot on our top things-to-do list. A reflective upside-down bean sculpture that is great for a selfie. This unique sculpture should be included in your 2 day Chicago Itinerary. 

4. Willis Tower

Head to Willis Tower to experience the SkyDeck with a glass balcony ledge that overlooks Chicago whilst the rest of the SkyDeck offers sweeping views of the surrounding states. This is open from 10am to 8pm but check ahead of your visit as it can close during poor weather.

Entrance costs $19.50 but is also included in the Chicago CityPass.

5. Wrigley Field

Watch the Chicago Cubs play in the oldest standing baseball stadium of America. Tickets can be purchased online but it is advised to do so in advance. Knowing how to visit Wrigley Field helps you plan the perfect trip to this iconic stadium.

6. 360 CHICAGO

Offering 360-degree views of this fabulous city, the 360 Chicago building offers an observation deck with cafe and bar for $19 for an adult ticket. Again, this is included in the Chicago CityPass if you choose to purchase it.

7. Magnificent Mile

Home to some of the best fashion stores, head to Magnificent Mile for some shopping as well as to eat in delicious high-end restaurants.

8. Deep Dish Pizza

Chicago’s deep-dish pizza is incredible and a must whilst in Chicago. Read our review of Gino’s East Pizza (also seen on Man Vs Food) for more details and pictures.

9. Lincoln Park & Zoo

Head to Lincoln Park and Zoo to meet some gorgeous animals; perfect for families. Open from 7am to 5pm most days, this is the place to enjoy a free day of fun.

10. Chicago Lakefront Trail

One of the things that makes Chicago beautiful is the lakefront and rivers running through the city. For a perfect afternoon, take a stroll along the lakefront trail, stop near a river, enjoy a picnic and unwind.

Chicago is the perfect place to visit, especially for a stopover or for a few days. We spent just 3 days in Chicago but because of the close proximity of these top attractions, we were able to explore everything we wanted to at a casual pace. If you have a few extra days in the city, make sure to take a few day trips from Chicago to see a different side of Illinois.

11. The Field Museum

The Field Museum is a huge natural hits museum and one of the best museums in Chicago for kids. It is home to a permanent collection of fossils and dinosaur remains, with Sue a Tyrannosaurus rex, being the most popular sight here; Sue is physically the largest Tyrannosaurs rex specimen ever discovered. 

12. The Art Institute of Chicago

Located in downtown Chicago, the art institute of Chicago is arguably one of the best art museums in the USA. You can find famous pieces of artwork from Edward Hopper and Grand Wood but also appreciate the incredible architecture of the museum too. The art museum is also included in the Chicago City Pass. 

13. Chicago Riverwalk

Stroll along the Chicago Riverwalk, a scenic path lined with restaurants, bars, and public art. It’s an ideal spot for a leisurely walk, kayaking, or enjoying a meal with a view of the river.

14. Museum of Science and Industry

Engage with interactive exhibits at the Museum of Science and Industry, one of the largest science museums in the world. Highlights include a World War II submarine, a coal mine replica, and a giant heart you can walk through.

15. Chicago Architecture River Cruise

Discover Chicago’s architectural heritage on a guided river cruise. Learn about the city’s iconic buildings and their history while enjoying views from the water.

16. The Violet Hour – Wicker Park

Experience a hidden gem in Wicker Park at The Violet Hour, a speakeasy-style cocktail lounge known for its expertly crafted drinks and intimate ambiance. It’s a perfect spot for a night out.

17. The Charnel House – Logan Square

Visit The Charnel House in Logan Square, a former funeral home turned performance space. Enjoy avant-garde theater, live music, and immersive art in this unique venue.

18. Logan Square Farmers Market

Visit the Logan Square Farmers Market on Sundays to sample fresh produce, artisanal goods, and local delicacies. It’s a great way to experience the community and support local vendors.

19. Myopic Books – Wicker Park

Browse through Myopic Books in Wicker Park, a three-story independent bookstore offering a vast selection of new and used books. It’s a haven for book lovers seeking hidden literary treasures.

20. Starbucks Reserve Roastery Chicago

A visit to the Starbucks Reserve Roastery on Michigan Avenue is a must for any Chicago bucket list. As the largest Starbucks in the world, this five-story coffee wonderland offers a truly immersive experience in the art and science of coffee.

Each level showcases something unique — from freshly roasted Reserve blends and craft coffee flights to bakery delights, creative cocktails, and even nitrogen-infused brews. The copper roasting cask spiraling through the center of the building is a stunning focal point, while the open layout allows you to watch beans being roasted and transported through transparent pipes across the floors.

Whether you’re a caffeine enthusiast or simply love beautiful spaces, this roastery combines coffee culture, design, and indulgence in a way that perfectly captures Chicago’s vibrant energy and innovation.

21. Harry Potter Shop Chicago

In April 2025, the Harry Potter Shop Chicago opened on the Magnificent Mile at 676 N. Michigan Avenue, becoming one of the city’s newest and most magical attractions. As the second standalone Harry Potter store in the U.S. and only the third in the world, it brings the Wizarding World to life right in downtown Chicago.

From the moment visitors step inside, they’re transported into a spellbinding space filled with themed rooms inspired by the Goblet of Fire, floating broomsticks, and flickering blue flames.

The highlight for many is the Butterbeer Bar — the largest in America — serving traditional, frozen, and ice cream versions alongside Chicago-exclusive treats. The store also features unique local merchandise, including Chicago-themed wizarding gear, exclusive spirit jerseys, mugs, and collectibles representing all four Hogwarts houses.

A special MinaLima gallery showcases the intricate artwork seen in the Harry Potter and Fantastic Beasts films, adding an artistic touch to this immersive experience. Whether you’re a lifelong fan or just looking for a one-of-a-kind stop on your Chicago adventure, the Harry Potter Shop is pure magic and a must for any bucket list.

What do you love about Chicago? Where else should we head to next time? Leave your suggestions in the comments below!