Chicago Bucket List: Top Things to Do
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Chicago is a city full of different foods and places to see. It has over 150 ethnic restaurants and 25 Michelin-starred spots. This makes it perfect for trying new things.
The city always has new events and activities. You can see famous landmarks and enjoy top attractions. Chicago has history, art, architecture, and entertainment for everyone.
Chicago has famous spots like the Willis Tower and amazing museums. There’s something for everyone here. It’s a great place to see iconic attractions and popular spots.
Explore the Art Institute of Chicago
The Art Institute of Chicago is famous in the city. It has over 300,000 works of art. Visitors can see Impressionist art and enjoy beautiful gardens.
It’s one of the biggest Chicago museums. It has art exhibitions for all ages.
It has a huge collection of Impressionist art, like Monet and Picasso. It also has American art, like Grant Wood and Georgia O’Keeffe.
Iconic Paintings and Exhibitions
The museum has famous paintings. You can see Vincent van Gogh’s self-portraits and Pablo Picasso’s The Old Guitarist. There’s also Grant Wood’s American Gothic.
It has rotating exhibitions. At least a dozen are on display at any time.
Architecture and History
The building is a work of art. It shows the city’s rich history. The museum offers free tours and self-guided tours.
With its gardens and outdoor spaces, it’s a top spot. It’s perfect for those interested in Chicago museums and the Art Institute of Chicago.
Stroll Through Millennium Park
Millennium Park is a top spot in Chicago, drawing in millions yearly. It’s famous for the Cloud Gate sculpture, known as “The Bean,” which gives amazing city views. The park also hosts outdoor concerts and events, like free summer festivals.
The park’s gardens and outdoor areas are perfect for relaxing. You can see the Jay Pritzker Pavilion for concerts and the Lurie Garden, covering 3.5 acres with many plants.
Millennium Park has lots of activities and events all year. You can join free yoga and Pilates classes or see public art. It’s easy to get to by bus or ‘L’ train. With art, culture, and fun, it’s a key place to visit in Chicago.
Some upcoming events in Millennium Park include:
- Summer Music Series
- Summer Film Series
- Grant Park Music Festival
- Chicago Gospel Music Festival
- Chicago Blues Festival
- Chicago Jazz Festival
These events show the park’s lively vibe and offer fun for all.
Visit Navy Pier for Family Fun
Navy Pier is a top spot for families in Chicago. It has lots of fun activities and rides. The Centennial Wheel is famous, reaching almost 200 feet high. It has gondolas that stay warm all year.
There’s lots to do here, like boat cruises and eating out. You can also shop for souvenirs. The Chicago Children’s Museum and Amazing Chicago’s Funhouse Maze are big hits. They offer fun and learning for kids.
Amusement Rides and Attractions
Here are some rides and attractions at Navy Pier:
- Centennial Wheel: a 200-foot tall Ferris wheel with climate-controlled gondolas
- Chicago Children’s Museum: a museum featuring interactive exhibits and a unique water room
- Amazing Chicago’s Funhouse Maze: a 4,000 square foot maze with interactive challenges
Dining and Shopping Options
Navy Pier has many places to eat and shop. You can try Giordano’s for deep-dish pizza or Molly’s Cupcakes for custom treats.
Navy Pier is perfect for families. It has rides, shows, and places to eat. It’s fun for everyone, whether you want excitement or a calm day.
Experience the Field Museum
The Field Museum is a top Chicago museum. It has a huge collection of natural history items. With over 4.5 billion years of history, it’s perfect for those who love dinosaur fossils or ancient cultures.
At the museum, you can see Sue, the biggest T. rex skeleton found. It’s 40.5 feet long and has a 600-pound skull. The Field Museum also has ancient Egyptian and Greek artifacts. These give a peek into the past.
Some of the museum’s best parts include:
- Seeing dinosaur fossils, like Sue and Maximo the Titanosaur
- Exploring ancient cultures, such as Egypt and Greece
- Learning about Earth’s history through fun exhibits
Plan to spend at least four hours at the Field Museum. You can get discounts if you live in Illinois, are a teacher, or in the military. The Field Museum is a top spot in Chicago. Its dinosaur fossils and exhibits make your visit unforgettable.

Enjoy the Views from Willis Tower
The Willis Tower stands tall in the Chicago skyline. It offers visitors an unmatched experience. The Skydeck on the 103rd floor lets guests see the city in all directions. On a clear day, you can spot up to four states.
The Skydeck’s Ledge is a glass floor balcony that sticks out 4.3 feet. It’s a thrilling spot, with just 1.5 inches of glass between you and a 103-floor drop. The Skydeck is open every day, with hours changing by day and season.
There are special packages for a better visit. The Golden Hour Package is for Monday to Friday sunsets. The Skydeck x Color Factory Views and Hues Bundle combines Skydeck views with Color Factory exhibits.
Skydeck Experience
The Skydeck offers more than just views. The lower level has an interactive museum on Chicago’s history, like the Great Chicago Fire. The Willis Tower is a top spot for anyone wanting to see the Chicago skyline.
360-Degree Cityscape
The Skydeck’s 360-degree views are amazing. You can see the Chicago skyline and its landmarks. It’s perfect for history buffs, architecture fans, or anyone wanting to see the city from above.
Discover the Shedd Aquarium
The Shedd Aquarium is a top Chicago aquarium. It offers a memorable visit for all ages. Located at 1200 S. DuSable Lake Shore Drive, it houses over 32,000 animals. These include dolphins, beluga whales, and penguins.
Some of the highlights of the Shedd Aquarium include:
- Marine life exhibits featuring a diverse range of species
- Interactive experiences, such as the Caribbean Reef and Polar Play Zone
- Daily feedings and encounters with divers and animals
Visitors can enjoy views of Lake Michigan and the city skyline. The aquarium is on the Museum Campus. With its history, architecture, and marine life, it’s a key spot for Chicago aquariums fans.

Walk the Magnificent Mile
The Magnificent Mile is a top spot for shopping in Chicago. It draws about 22 million people every year. This famous part of Michigan Avenue has over 460 shops, including luxury brands and big department stores.
Walking here, you’ll see iconic landmarks and beautiful buildings. There are more than 275 places to eat. You can visit the Tribune Tower and the Water Tower, both famous for surviving a big fire in 1871.
World-Class Shopping
The Magnificent Mile has shops for everyone. You can find the original American Girl Place and the 360 CHICAGO observation deck. The deck gives you amazing views from 1,000 feet up.
Iconic Landmarks and Architecture
There are cool attractions like TILT at 360 CHICAGO. It lets you see the city from a new angle. You can also take a boat cruise on the Chicago Riverwalk. It’s great for seeing buildings and adds to the fun of visiting the Magnificent Mile.
Whether you love Chicago shopping, food, or just exploring, the Magnificent Mile is a must-see. Its history, architecture, and attractions make it unforgettable for visitors from everywhere.
Attend a Chicago Cubs Game
Going to a Chicago Cubs game at Wrigley Field is unforgettable. Wrigley Field, one of the oldest ballparks, has a special atmosphere. It’s filled with tradition and excitement.
The Chicago Cubs have a long history. Their home, Wrigley Field, is a key part of it. With its famous scoreboard and ivy walls, it’s a top spot for baseball fans.
At a Cubs game, the vibe is electric. Fans sing “Take Me Out to the Ball Game” in the seventh inning. The stadium also has many food and drink choices, including gluten-free, kosher, vegetarian, and vegan options.
Wrigley Field is great for families too. It has family restrooms and a kids’ play area.
Wrigley Field Experience
Some top things about Wrigley Field include:
- Autographs from players during batting practice
- Running the bases after the game on Kids Sunday games
- Access to gluten-free, kosher, vegetarian, and vegan food options
- Family-friendly amenities like family restrooms and a kids’ play area
The Excitement of Baseball Season
The Chicago Cubs season starts in March, with the home opener in April. Fans get to enjoy baseball season at Wrigley Field. It’s a place of unique atmosphere and rich history.
Whether you love the Cubs or just want a fun time, seeing a game at Wrigley Field is a must.

Dive into Chicago’s Food Scene
Chicago is a food lover’s dream, with many cuisines and dining spots. It’s famous for deep-dish pizza and hosts many food festivals. The Taste of Chicago is a highlight, offering a variety of foods.
Some top Chicago food choices include:
- Deep-dish pizza from Uno Pizzeria & Grill
- Italian beef sandwiches from Al’s Italian Beef
- Chicago-style hot dogs from Portillo’s
Chicago also has many food festivals all year. The Taste of Chicago and the Chicago Food Festival are highlights. They show off the city’s food diversity.
Looking for American comfort food or international dishes? Chicago food has it all. With its rich food history and many dining spots, Chicago is perfect for food lovers.
Food Festival | Description |
---|---|
Taste of Chicago | A five-day festival featuring food from over 70 restaurants and vendors |
Chicago Food Festival | A celebration of the city’s diverse culinary scene, with food, drinks, and live music |
Enjoy Jazz and Blues Music
Chicago is famous for its lively music scene. It’s especially known for Chicago jazz and blues music. The city has many historic clubs where you can see live music by artists from around the world.
Places like the Green Mill and Buddy Guy’s Legends are must-visits. They play live music every night.
Some top spots include:
- Kingston Mines, the biggest and oldest blues club in Chicago, has blues shows every night until late.
- Jazz Showcase, a place for jazz legends since 1947, has a strict “no-talking” rule during shows.
- Andy’s Jazz Club, with shows seven nights a week, starts at 5 PM.
The city also has big live music festivals. The Chicago Jazz Festival and the Blues Festival celebrate the city’s music history. Chicago’s mix of Chicago jazz and blues music makes it a top spot for music fans.

Take a River Architecture Tour
Chicago is famous for its amazing Chicago architecture. Many historic buildings line the river. Visitors can take a guided river tours to learn about the city’s history and architecture.
The tour shows off the city’s skyline. You’ll see the Willis Tower, the Tribune Tower, and the Wrigley Building. It also tells you about their design and construction.
The Chicago architecture tour is a 90-minute cruise. It goes along the Chicago River, giving a special view of the city. You can pick from group or private tours. It’s voted the #1 boat tour in North America by USA Today readers.
Some key highlights of the tour include:
- Admission to the Chicago Architecture Center as an event extra for just $5
- Priority Boarding tickets starting at $69.00
- General Boarding tickets starting at $54.00, with the option to add a visit to the Chicago Architecture Center for $5.00
- A portion of each ticket fee supports the educational work of the Chicago Architecture Center
The tour runs rain or shine. There are two levels on the boats: an open-air upper deck and a covered salon. The boats are wheelchair-accessible, making it for everyone. So why not take a river tours and see the beauty of Chicago architecture and its historical buildings?
Explore Lincoln Park Zoo
The Lincoln Park Zoo is in the heart of Chicago. It’s a great place for families and nature lovers. It’s free, making it a special spot to see many animals.
At the zoo, you can see lions, monkeys, and penguins. It’s fun and educational for everyone. It’s a place where learning and fun go together.
The zoo has lots of activities for families. You can take tours, meet animals, and enjoy concerts in summer. It also works hard to save endangered animals and their homes.
Visiting the Lincoln Park Zoo is a great way to spend the day. It’s free, has lots of animals, and fun activities. It’s a top spot in Chicago, loved by many.