Wander Through the Windy City - 20 Things to Do in Chicago

The City of Chicago in Illinois is the third most populous city in the United States. The hometown of Kanye West and Jenny McCarthy is known for its towering skyscrapers, jazz music, Chicago-style hot dog, and deep-dish pizza. 

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If you're planning a trip to Chicago soon, you better read the list below. We've collected some of the most interesting places to see and things to do in Chicago just for you.

1. Field Museum

Come see the giant fossils of dinosaurs in one of the world's leading natural history museums. With almost 40 million specimens, Field Museum will take you to a great journey across time since primitive forms of life started to appear on the surface of our planet.

2. Navy Pier

Located on the shoreline of Lake Michigan, Navy Pier is an entertainment hub with lots of attractions and culinary options. Ride the musical carousel and adrenaline-pumping swings, then hop into Centennial wheel for spectacular views of Chicago skyline. 

3. Grant Park

The large urban park, often dubbed as "Chicago's front yard", is strategically situated in Chicago's central business district in the Loop community area. Wander through its massive gardens and lawns while enjoying the scenery of Chicago's skyscrapers and Lake Michigan. 

4. Millennium Park

A section of Grant Park is dedicated to a new public park project called Millennium Park. Since its opening in 2004, the park has become a major attraction dotted with contemporary art and urban structures such as Cloud Gate, Crown Fountain, and Jay Pritzker Pavilion.

5. Skydeck Chicago

Attached to the 103rd floor of Willis Tower (formerly Sears Tower), Skydeck Chicago offers breathtaking view covering up to four states from one of the tallest buildings in the United States. The glass deck is especially an amazing experience where you feel like walking in the sky.  

6. Lakefront Trail

The path spanning some 18.5 miles (29.8 km) along the western shore of Lake Michigan is a favorite among joggers, cyclists, and skateboarders. Chicago Lakefront Trail (LFT) connects many attractions in Chicago, including Navy Pier, many parks, and museums. 

7. The Chicago Theatre

The vintage landmark of Chicago is a glamorous venue for various performances, from stage plays and magic shows to lively music concerts. Walk under its iconic sign and be awed by its French baroque interior design as you wait for the performers to enter stage. 

8. 360 Chicago

Jump onto one of the fastest elevators in the United States launching you to the 94th floor of the John Hancock Building where 360 Chicago can be found. The spectacular observation deck is equipped with tilting glass for sensation of hovering above and a bar for you to relax after. 

9. Chicago Riverwalk

The pedestrian-friendly public space is a popular destination on the south bank of the main branch of Chicago River. Spanning some 1.25 miles (2 km), Chicago Riverwalk is divided into four sections (Market, Civic, Arcade and Confluence) with cozy coves, restaurants, and bars along the way.


10. Lincoln Park

The Chicago's largest park stretches for 7 miles (11 km) along Lake Michigan with beaches, nature reserves, and recreational areas. Lincoln Park also features a zoo, botanical garden with greenhouse, several harbors, and various sport facilities, from basketball court to skate park. 

11. Maggie Daley Park

Bring your kids to play in this unique urban landscape. Maggie Daley Park is equipped with extensive children's playground, climbing walls, and ice skating ribbon during winter. The is also an aesthetic pedestrian pathway called the BP Bridge linking Maggie Daley Park and Millennium Park. 

12. Shedd Aquarium

One of the oldest aquariums in North America, Shedd Aquarium contains some 32,000 animals from 1,500 species, including fish, birds, reptiles, amphibians, insects, corals, and marine mammals such as dolphins and belugas spread in several living exhibitions. 


13. The Art Institute of Chicago

Discover a vast collection of art from around the globe in this important art museum. The Art Institute of Chicago is home to no less than 300,000 art pieces, from ancient Greek and Egyptian sculptures to native American artifacts and French impressionist paintings. 

14. Wrigley Field

The baseball park on West Addison Street has been home to Chicago Cubs for more than a century. Take pictures on its iconic marquee sign, and feel the energetic atmosphere as you watch the baseball game along with other die-hard fans of baseball. 

15. Garfield Park Conservatory

The sizeable greenhouse conservatory located in Central Park Avenue is one of the largest indoor gardens in the world. Take a deep breath and explore the world of plants and flowers in a meticulously arranged setting. 

16. The 606

An abandoned railway is turned into a captivating elevated park and pedestrian pathway on the west side of Chicago. The Bloomingdale Trail, or simply called the 606, spans 2.7 miles (4.3 km) through several parks. You can explore it by foot or riding bicycle. 

17. Chicago Boat Tour

Get into the boat taking you through the Chicago River with views of tall buildings or explore the shoreline of Lake Michigan. There are many boat tour services you can choose, from simple sightseeing tour to fancy cruise with lunch and dinner option. 


18. Museum of Contemporary Art

The voguish art museum holds the artworks of modern and contemporary artists such as Andy Warhol, Jeff Koons, and Cindy Sherman. If you love seeing surrealist, minimalist, or post-modernist art from 1945 until today, then this is the perfect place for you. 

19. Oriental Institute Museum

The Oriental Institute at the University of Chicago is among the most respected research centers devoted to the study of ancient Near East. Their archaeological museum contains precious artifacts from ancient Sumerian, Babylonian, Persian, Egyptian, and other Near Eastern civilizations.


20. Adler Planetarium

Satisfy your curiosity of stars and galaxies at America's first planetarium. Adler Planetarium features three theaters and a large space science exhibition where you can see models of planet, sample of real meteorite, and celestial sphere along with information from the experts.  

Have fun and enjoy your vacation! If you know other engrossing places to see and things to do in Chicago, please tell us in the comment section.

Don't forget to book your favorite hotel in Chicago! Click here to book now. 

Hope you have a great time in Chicago!

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