What To Do On A Rainy Day In Chicago, Illinois, USA - Updated 2023


Located in northeastern Illinois on the southwestern shores of Lake Michigan, Chicago is the third most populous city in the United States. Chicago is known for some of its notable landmarks such as; the Art Institute of Chicago, Museum of Science and Industry, and its famous outdoor public art, world-class museums, theaters, skyscrapers, Michelin-star restaurants, upscale shopping along the Magnificent Mile and waterfront. Its culture comprises of visual arts, literature, film, theater, comedy (especially improv comedy), music (especially jazz, blues, soul, hip hop, gospel, and house) and a distinctive fine art tradition. O'Hare International Airport in Chicago is one of the busiest airports in the world and the region also has the largest number of U.S. highways and railroad freight. With its outstanding infrastructure, read on to know more about things to do on a rainy day in Chicago, Illinois, USA.

1. Visit a speakeasy pub (from USD 880.0)

Start this evening adventure by enjoying chauffeured luxury transportation from your hotel. Led by a professional local historian guide in a period dress, go through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone in the 1920s that are still in operation today. At an additional cost, drink prohibition era cocktails while listening to the rampant racketeering and bootlegging stories of the era. You can also wear a period dress for fun. Enjoy this thrilling experience that will take you back in time as you gain an insight into their world of crime.

Private Speakeasy Pub Crawl in Chicago with Local Historian

Duration: 3 hours

5 reviews

2. Tour the Field Museum of Natural History

what to do on a rainy day in chicago | tour the field museum of natural history
Source: www.viator.com

Visit this natural history museum in the city of Chicago which is one of the largest museums in the world. Alone or on a free docent-led tour, discover various world-renowned exhibitions such as the Hall of Gems, Hall of Jades that has Chinese artifacts, Sue (one of the best-preserved Tyrannosaurus Rex fossils ever found that is 40 feet (12 meters) in length and 13 feet (4 meters) long), Inside Ancient Egypt that has 23 Egyptian mummies and floor to ceiling hieroglyphs in the Mastaba tomb of Unis-Ankh, Underground Adventure where you “shrink” to 1/100th of your natural size to take a closer look at the diversity of life soil supports, the Ancient Americas and Dinosaur Hall with giant sloths, woolly mammoths and dinosaurs. A 3D movie is subject to availability. Book your ticket in advance for easier logistics and spend your time exploring and learning about natural history.

Field Museum of Natural History All-Access Pass

Duration: 1 to 8 hours

83 reviews

3. Visit LEGOLAND Discovery Center with the kids (from USD 26.0)

Wondering where to take your kids for a fun day out on a rainy day? LEGOLAND Discovery Center in Schaumburg is the place. Kids can indulge in fun activities such as; brick-building, see a mini replica of famous Chi-town landmarks made from nearly two-million LEGO pieces, take a LEGO jungle expedition, ride through a forest in a dragon car and help destroy the skeleton army in the Kingdom Quest Laser Ride, watch a short movie with added special effects such as wind, rain and snow at LEGO Studios 4D Cinema, pedal bike rides that make you fly up in the air and a factory tour where you can actually see how LEGO bricks are made. Adults can only enter when accompanied by kids who ideally should be between 3-12 years. Create fun memories with your kids through very engaging and enjoyable activities.

LEGOLAND Discovery Center Chicago Admission Ticket

Duration: 3 hours

84 reviews

4. Visit the Chicago skydeck (from USD 44.0)

Visit the Skydeck, Chicago’s highest point, located on the 103rd floor of the Willis Tower and enjoy a breathtaking view of Chi-town’s skyline with its numerous skyscrapers and top attractions like Wrigley Field, the Navy Pier, and Millennium Park. On a clear day, you can see up to 50 miles (80.5 km) out. Feel the adrenaline rush as you walk out to the ledge, a glass box-like balcony that extends 4.3 feet (1.3 meters) from the building that is 1,353 feet (412.4 meters) off the ground. Explore interactive displays and exhibits about Chicago history that are suitable for the entire family.

Skydeck Chicago Admission Ticket

Duration: 90 to 120 minutes

1100 reviews

5. Visit Macy's State Street store (from USD 12.0)

visit macy's state street store
Source: www.viator.com

Enjoy a guided one-hour tour that starts at 11.30 am in this national historic landmark. Explore the different levels at Macy’s and get to see the Burnham fountain, the great granite pillars, great clocks, Tiffany vaulted ceilings and the Walnut Room restaurant where you will taste the Frango-mint chocolate. A 10 percent visitor savings pass is given after the tour which you can use to shop and dine in this historic nine-floor building.

Chicago's State Street Historical Store Tour

Duration: 45 minutes

6. Visit the Museum of Science and Industry (from USD 20.0)

visit the museum of science and industry
Source: www.viator.com

Visit the largest science museum in the country for a phenomenal experience. Get to stand before a 40 foot (12 metres) water vapor tornado, trigger an avalanche as you rotate an avalanche disk, generate a tsunami in the tsunami generator, see bolts of lightning flashing above you, transmit your pulse to a 13 foot (4 metres) interactive 3-D heart, board a 727 jet plane hanging from the ceiling, watch chicks hatch in an incubator, explore the mirror maze, run in a human-sized hamster wheel and watch a film in the giant dome theater. There are additional charges for timed-entry experiences and special exhibits. Arrive early enough to allow you ample time to experience all these unique exhibits.

Museum of Science and Industry Chicago

7 reviews

7. Enjoy a performance at the Lyric Opera House (from USD 112.0)

enjoy a performance at the lyric opera house
Source: www.viator.com

Enjoy a legendary performance at one of the largest opera halls in the world. The Lyric Opera House presents different performances throughout the year at the splendid 3,563-seat Ardis Krainik Theater. The architecture is detailed and unique and the art-deco lobby is magnificent. The theater screams elegance and has great acoustics. Refreshments are available before performances and during intermissions which you can pre-order at one of the bars in the lobby. Get to experience one of Lyric’s memorable performances that will give you the chills in this glorious theater.

Cinderella at the Lyric Opera House

8. Attend a comedy show (from USD 26.0)

Laugh your heart out at Frances’ Cocktail Lounge and Grill, a 50-year-old family-owned bar located in Chicago’s south side of the Greater Grand Crossing neighborhood. This bar was featured in the Fox Series Rel. Get to interact with locals and learn about local history at the center of Chicago culture which is also a favorite spot for urban comedians and Def Jam stars. The show is hosted by a local comedian. The minimum entry age is 21 years. You can also enjoy the famous finger-licking ribs at Lem’s Bar-B-Q or satisfy your sweet tooth at Brown Sugar Bakery which is next door. Definitely, a must go to place when in Chicago.

Black Comedy and Social Scene

Duration: 2 hours

9. Take piano lessons (from USD 136.0)

Interested in learning how to play the piano? Learn from an award-winning, internationally-acclaimed Steinway artist and classical pianist who is also a music director and an educator. Take piano lessons instructed by Susan Merdinger at her private residence in Highland Park, Chicago. You can purchase a package of one, five or ten piano lessons. Susan Merdinger performs as a solo Steinway artist, visiting artist of the Chicago Symphony Orchestra and is a frequent guest artist on WFMT, Chicago’s Classical Radio Station. Get to learn from the very best, who has excelled as a classical pianist herself.

Piano Lessons with Susan Merdinger

Duration: 1 hour

10. Explore the Art Institute of Chicago (from USD 35.0)

The Art Institute of Chicago, the second largest in the US, is a world-class art museum located in Grant Park. It houses an encyclopedic collection that includes iconic works such as Claude Monet, Georges Seurat, and Pablo Picasso. The departments to be explored include African, Indian, Asian and American Art, Architecture and Design, European Decorative Art, European Painting and Sculpture, Modern and Contemporary Art, Textiles, Photography, and Print and Drawings. Skip admission lines and gain expedited access to collection galleries and special exhibitions using a Fast-Pass admission ticket. At the end of the tour, you will have an idea of the culture in different parts of the world during different time periods.

Art Institute of Chicago Fast Pass Admission in Grant Park

Duration: 3 hours

48 reviews

Explore Chicago even on a rainy day

With all these indoor activities and adventures that are entertaining, thrilling and educative, Chicago, Illinois, USA offers a lot to do individually or with family. Do not let the rains stop you from exploring such an architectural city full of history and culture.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Herine is from Nairobi, the capital city of Kenya. As a travel enthusiast, she always takes interest in learning about and visiting new places. She has traveled to many places within the country,...Read more

 Want to contribute as a Local Expert?
Explore Chicago
Looking for accommodation?
Good things are meant to be shared!