12 Best Things To Do in CHICAGO, Including Indoor Skydiving

12 Best Things To Do in CHICAGO, Including Indoor Skydiving
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Chicago, the Windy City, is a treasure trove of experiences, blending world-class attractions, vibrant neighborhoods, and rich cultural history.

Whether you're a first-time visitor or a local looking to rediscover your city, there’s always something extraordinary to explore. From architectural marvels to deep-dish delights, Chicago offers a perfect balance of iconic landmarks and hidden gems that cater to every interest.

As someone who’s spent years discovering the best things to do in Chicago, I can confidently guide you to experiences that are truly unforgettable. Start with a stroll along the Magnificent Mile, where luxury shopping and historic landmarks meet. Don’t miss the Art Institute of Chicago, home to an unparalleled collection of masterpieces. For stunning views, the Skydeck at Willis Tower and 360 Chicago Observation Deck offer breathtaking perspectives of the city skyline.

If you’re a foodie, indulge in a slice of Chicago deep-dish pizza or explore the thriving dining scene in neighborhoods like Wicker Park and Logan Square. Outdoor enthusiasts can unwind at Millennium Park, famous for the Cloud Gate sculpture (aka "The Bean"), or take a relaxing cruise on the Chicago River to marvel at the city’s legendary architecture. Whatever your passion, Chicago promises endless adventure, culture, and charm.


Best Indoor Things To Do in CHICAGO


1. 360 CHICAGO Observation Deck (John Hancock Tilt): Best Overall

Chicago observation deck - Best indoor things to do chicago - GRANDGOLDMAN.COM

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360 CHICAGO Observation Deck is located on the 94th floor of 875 N. Michigan, offering breathtaking views of the Chicago Skyline and Lake Michigan. The concourse level features an interactive exhibit showcasing the history and diverse cultures of Chicago's neighborhoods. 


Take a 40-second elevator ride to the observation deck and enjoy panoramic views of the city, lakefront, and neighboring states. Download the Magnicity App for a guided tour with interesting facts and recommendations.

For an adrenaline rush, try TILT, a unique experience where you can lean out over Michigan Ave at a 30-degree angle. Don't forget to visit CloudBar for delicious Chicago snacks and cocktails, and take a stroll on CloudWalk for a photo-worthy moment in the clouds.




2. LEGOLAND® Discovery Center Chicago: Best for Kids

2. LEGOLAND® Discovery Center Chicago: Best for Kids - Best indoor things to do chicago - GRANDGOLDMAN.COM

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LEGOLAND® Discovery Center Chicago offers a vibrant and thrilling LEGO® World for families to enjoy. With 12 unique attractions and activities, there is something for everyone. Experience the interactive Kingdom Quest adventure ride, watch The LEGO® Movie ™ A New Adventure at the 4D LEGO Cinema, and soar into the sky on Merlin's Apprentice Ride. 


Explore MINILAND® and marvel at the Chicago cityscape made entirely of LEGO Bricks. Build and add colorful additions to LEGO® Friends Heartlake City, and embark on a jungle expedition to meet life-size LEGO® jungle animals. Lastly, create and race LEGO racing cars on the test track.




3. Two Flight Indoor Skydiving Experience: Best for Daredevils

Two Flight Indoor Skydiving Experience: Best for Daredevils - Best indoor things to do chicago - GRANDGOLDMAN.COM

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Experience the thrill of skydiving without ever leaving the ground with this indoor skydiving adventure. Step into a vertical wind tunnel and feel the sensation of free falling and soaring through the air. Get geared up with a flight suit, helmet, and goggles, and receive introductory training from an experienced instructor. 


Then, enter the flight chamber and let the rushing wind lift you off your feet. Spin, hover, and enjoy the adrenaline rush before safely landing back on solid ground. Take a moment to catch your breath and then do it all over again.

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4. Medieval Torture Museum with Audio Guide and Ghost Hunting

Medieval Torture Museum with Audio Guide and Ghost Hunting - Best indoor things to do chicago - GRANDGOLDMAN.COM

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The expansive Medieval Torture Museum in Chicago offers a chilling exploration of humanity's dark past, showcasing a wide range of punishment, torture, and execution methods.

Spanning over 6000 sq. ft., the museum houses an extensive collection of devices used for torture, interrogation, restraint, and execution. Additionally, visitors can witness lifelike wax sculptures portraying both executioners and their unfortunate victims in gruesome detail.

 




5. Art Institute of Chicago

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Discover one of the world's finest art collections at The Art Institute of Chicago. Immerse yourself in the museum's 1 million square feet of exhibit space, featuring 300,000 works of art. Experience the mobile tour, complete with audio guides and a location-aware map, to navigate through the museum's impressive collection.


Admire the largest collection of impressionist art outside of Paris, including Seurat's A Sunday on La Grande Jatte and Caillebotte's Paris Street; Rainy Day. Don't miss iconic American works like Hopper's Nighthawks and Wood's American Gothic. Don't forget to visit the gift shops for art-inspired souvenirs.




6. Trickery Chicago Magic Show

Trickery Chicago Magic Show - Best indoor things to do chicago - GRANDGOLDMAN.COM

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Experience less ordinary entertainment at Trickery Chicago Magic Show! Prepare to be delighted by an intimate and hilarious performance. Located at 3453 N Halsted Street, the theater opens its doors 15 minutes before showtime, offering general admission seating. 

Guests aged 21 and above can bring their own beverages, and cups and bottle openers are provided if necessary. Please note that ice is not available on-site, but you can find a 7-Eleven conveniently located at 3407 N Halsted. Get ready for an unforgettable one-hour performance!

 

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7. Blue Man Group Chicago

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Blue Man Group, a long-running show in Chicago, offers a unique audiovisual experience that is both hilarious and family-friendly. The show combines innovative music and technology with witty social commentary. As you make your way through the black-light artwork in the intimate Briar Street Theatre, you'll find your seat and witness the latest version of Blue Man Group.

This new iteration incorporates new songs and tech-focused props, such as the 'GiPad,' a massive tablet. Led by three bald, blue men, the show takes you on a captivating multimedia journey filled with drumming, neon lighting, and paint splattering. It is a celebration of culture, comedy, and color, providing both entertaining musical performances and thought-provoking insights into our fast-paced world.




8. Chicago: Field Museum of Natural History

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The Field Museum of Natural History in Chicago offers a wide range of world-renowned natural history exhibitions. From dinosaurs and ancient artifacts to cultural insights and groundbreaking science, there is something for everyone. Explore the Underground Adventure exhibit to learn about subterranean life, admire gemstones in the Hall of Gems, and discover the Ice Age mammoth hunters and the temples of the Inca and Aztecs. 

Don't miss the Dinosaur Hall Evolving Planet exhibit, where you can encounter giant sloths, woolly mammoths, Sue, and Maximo. Upgrade to the All-Access Pass for a 3-D movie and special exhibitions, or choose the Early Access VIP Tour for an exclusive experience with the museum's dinosaurs. With a Discovery Pass, you can enjoy general admission to the museum and add a ticketed exhibition or a 3D movie to your visit.




9. BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago - Best indoor things to do chicago - GRANDGOLDMAN.COMPhotos & Skip-the-line Tickets:  LEARN MORE

Discover your inner street artist at Studio W.I.P. Chicago's BYOB Spray Paint 'n' Sip workshop. This unique and interactive experience allows you to explore the world of spray paint and street art. Don't worry if you're not the most creative person, as the workshop is curated by Studio W.I.P. artists. 

Learn about aerosol application and technique, stencil design and application, and graffiti style and application. And the best part? You get to choose a mini-canvas from the communal wall to take home with you at the end of the workshop.




10. Sloomoo Institute

Sloomoo Institute - Best indoor things to do chicago - GRANDGOLDMAN.COM

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If your kids love slime, they will feel like heaven at the Sloomoo Institute. Immerse yourself in over 30 vats of slime, discovering their unique textures, scents, and sounds. Get creative at the DIY Bar and design your own custom slime to take home. Have a blast slingshotting slime at your loved ones behind plexiglass, capturing unforgettable moments. 

Transform into a virtual slime creature and walk across 350 gallons of slime at Lake Sloomoo. Engage with the fascinating characters of the Sloomooverse, uncover your personalized "slime name," and indulge in the relaxing ASMR sound station. Don't forget to visit the one-of-a-kind slime-themed store before you leave.




11. Candle Making Class On Magnificent Mile

Candle Making Class On Magnificent Mile - Best indoor things to do chicago - GRANDGOLDMAN.COM

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Discover a unique and creative experience on Chicago's Magnificent Mile with a Candle Making Class. Perfect for a date night, girl's night out, corporate events, or even a solo adventure. 

Learn the art of making 100% soy wax candles, from step by step techniques to creating personalized fragrances for each candle. All the necessary supplies, including soy wax, fragrances, and vessels, are provided for you to craft your own 8 oz custom candle. Classes last between 60-75 minutes, ensuring a fun and interesting session.




12. International Museum of Surgical Science

International Museum of Surgical Science - Best indoor things to do chicago - GRANDGOLDMAN.COM

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The International Museum of Surgical Science in Chicago is dedicated to showcasing the history of surgery and medicine. With over 10,000 square feet of public galleries, the museum houses a remarkable collection of medical artifacts, instruments, and artwork. 

The museum's mission is to educate and inspire visitors by highlighting the advancements and developments in surgery and related subjects. The collection includes over 7,000 medical artifacts from around the world, as well as over 600 paintings, prints, and sculptures. Notable pieces include an Austrian amputation saw from the 1500s and original X-rays taken by radiology pioneer Emil Grubbé.

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More Fun Things to Do in Chicago (Expedia)

Chicago is famous for its stunning architecture (think Willis Tower and Wrigley Field), deep-dish pizza, jazz music, and vibrant art scene (Art Institute of Chicago). Additionally, its lakefront, diverse neighborhoods, and rich history draw visitors worldwide.

Whether you're an adventurer, a foodie couple, or a family looking for fun, there are great activities for everyone in Chicago.


How to Choose Indoor Things to Do in Chicago

 

 

1. Interests

What sparks your curiosity? Art, history, science, or something more unusual? Align your choices with your passions for a truly fulfilling experience.

2. Travel Style

Are you a solo adventurer, a family on the go, or a couple seeking romance? Consider group dynamics and age preferences when selecting activities.

3. Budget

Chicago caters to all budgets. From free museums to upscale experiences, choose options that fit your financial comfort zone.

4. Accessibility

Ensure chosen activities align with any physical limitations or accessibility needs.

5. Time Constraints

Plan activities that fit your schedule, whether you have a full day or just a few hours to spare.

 



When to Consider Indoor Things to Do in Chicago

  • Chicago's unpredictable weather: Escape the scorching summer heat, the bone-chilling winters, or the occasional rainy day.
  • Seeking unique experiences: Uncover hidden gems or cultural treasures beyond the beaten path.
  • Family-friendly fun: Rain or shine, keep the little ones entertained and engaged.
  • Romantic getaways: Create intimate moments in captivating settings, regardless of the weather.
  • Group outings: Bond with friends or colleagues in unique and memorable indoor spaces.

Remember, this is just a starting point. With these tips and Chicago's diverse offerings, you're sure to find the perfect indoor adventure to suit your style and preferences.

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Best Indoor Things To Do Chicago FAQ


What is Chicago best known for?

Chicago is famous for its stunning architecture (think Willis Tower and Wrigley Field), deep-dish pizza, jazz music, and vibrant art scene (Art Institute of Chicago). Additionally, its lakefront, diverse neighborhoods, and rich history draw visitors worldwide.

Is Chicago worth visiting in winter?

Absolutely! While winters can be chilly, Chicago embraces the season with festive cheer, Christkindlmarket, twinkling lights, and cozy indoor activities like world-class museums and theaters.

How do you occupy kids on a rainy day?

Chicago offers plenty of kid-friendly indoor options: explore Shedd Aquarium's underwater wonders, play at Maggie Daley Park's indoor climbing wall, or spark imaginations at the Museum of Science and Industry.

 



 

What food is Chicago most famous for?

Deep-dish pizza is the king, with its thick crust and generous toppings. But don't miss Chicago-style hot dogs, Italian beef sandwiches, and Garrett Popcorn for a sweet treat.

Who is the most famous person from Chicago?

Many notable figures hail from Chicago, making it hard to pick just one! Barack Obama, Oprah Winfrey, Michael Jordan, and Al Capone are some of the most recognized names.

Are winters worse in Chicago or New York?

Both cities experience cold winters, but Chicago tends to be slightly colder with more snowfall. However, both offer unique winter experiences and charm.

What is the best month to visit Chicago?

Shoulder seasons (April-May, September-October) offer pleasant weather and fewer crowds. Summer brings vibrant festivals and outdoor activities, while winter boasts festive magic and cozy indoor attractions.

What is the coldest month to visit Chicago?

January is typically the coldest month, with average lows around 17°F (-8°C). However, even December and February can be quite chilly.

 

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Is Chicago Riverwalk open in winter?

Partially! While some restaurants and shops close, the scenic walkway itself remains open for strolls and enjoying the wintery landscape.

Why is Chicago called Windy City?

There are two main theories: 1) strong winds due to its location on the Great Plains, and 2) the city's politicians' reputation for "windy" speeches.

Why is Chicago so special?

Chicago's unique blend of urban energy, rich history, diverse neighborhoods, and cultural offerings creates a truly special atmosphere. Its friendly people, delicious food scene, and iconic landmarks make it a truly unforgettable destination.

Where can I go on a rainy day?

Chicago has numerous rainy day options: dive into the Art Institute's vast collection, explore the Field Museum's natural wonders, catch a Broadway show at the historic Oriental Theatre, or indulge in retail therapy at Water Tower Place.

How do you get rid of boredom on a rainy day?

Embrace the cozy vibes! Read a book at a quaint cafe, try a new recipe, learn a new skill online, or have a board game marathon with friends or family.

 



 

What food can you not miss in Chicago?

Deep-dish pizza is a must-try, but don't miss the iconic Chicago-style hot dog with its unique toppings. Italian beef sandwiches and Garrett Popcorn's gourmet flavors are also local favorites.

What are 4 typical dishes from Chicago?

  1. Deep-dish pizza: Thick crust, chunky tomato sauce, and generous toppings.
  2. Chicago-style hot dog: All-beef frankfurter with poppy seed bun, mustard, relish, sport peppers, tomato, onion, celery salt, and optional pickle spear.
  3. Italian beef sandwich: Thinly sliced roast beef dipped in gravy, served on Italian bread with giardiniera relish.
  4. Garrett Popcorn: Gourmet popcorn in unique flavors like Chicago Mix (caramel and cheese) and Garrett Mix (nuts and cheese).

What Sandwich is Chicago famous for?

Chicago is known for two iconic sandwiches: the Italian beef and the Chicago-style hot dog. Deciding which one reigns supreme depends on personal preference, as both hold special places in the city's culinary heart.

  • Italian beef: Imagine thinly sliced roast beef piled high on crusty Italian bread, dipped in savory gravy with giardiniera relish for a spicy kick. This hearty sandwich comes in variations like "wet" (soaked in gravy) or "dry" (with gravy on the side).
  • Chicago-style hot dog: Forget all-the-works hot dogs you know. This version boasts a steamed all-beef frankfurter nestled in a poppy seed bun. The toppings are key: yellow mustard, chopped onion, neon green relish, tomato slices, a dill pickle spear, sport peppers, celery salt, and optional hot peppers. Every bite bursts with flavor and tradition.

While both are tasty, the Italian beef might have a slight edge in popularity contests. Ultimately, the best way to decide is to try both and see which one conquers your taste buds.

 

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Author

Alicia Foster

Alicia is a trailblazer in luxury travel and all-inclusive resorts. Armed with a master's degree in Tourism Management, she has not only explored the hidden gems of the Caribbean, but has also collaborated with renowned hospitality brands. Her words are a gold mine for choosing the perfect accommodation.

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