Chicago Things to Do

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Unleash the excitement at Six Flags Great America Chicago, the ultimate destination for thrill-seekers and families alike. Dive into the adventure with over 75 rides, from the towering drops of Goliath to the splashy fun of Hurricane Harbor. The whole family will be thrilled by the new addition in 2024, Sky Striker, a high-flying, soaring adventure. Details
TripAdvisor user rating 4.00 out of 5
2752 Reviews
$89.99 $52.94
Total Price: $56.10 (USD)
You Save: $37.05

360 CHICAGO

Chicago
Get ready for an unforgettable experience at the 360 Chicago Observation Deck, located on the 94th floor of 875 North Michigan Avenue (John Hancock Center)! With 360 Chicago tickets, soak in breathtaking panoramic views of the Windy City and Lake Michigan from 1,000 feet above the Magnificent Mile. Elevate your Chicago trip with this must-see attraction! Details
TripAdvisor user rating 4.50 out of 5
11137 Reviews
$30.00
Total Price: $33.30 (USD)
One of the country’s longest-running dinner attractions, Medieval Times Dinner and Tournament Illinois, offers a fun and exciting way to enjoy a feast with family or friends. Guests can enjoy a banquet-style four-course feast (without silverware) while watching six brave knights compete in skill games atop their beautiful Andalusian stallions. Details
TripAdvisor user rating 4.50 out of 5
1022 Reviews
$66.19
Total Price: $71.36 (USD)
Step aboard the Shoreline Architecture River Cruise from Navy Pier and discover the magic of the Windy City’s architectural wonders! Glide past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide provides detailed descriptions. Kids age 2 and under are free, and the tour is dog-friendly, too! Details
$53.70 $46.99
Total Price: $52.50 (USD)
You Save: $6.71
To say that the bald, brilliant and hilarious blue men march to the beat of their own drum is an understatement. This loud, bright and over-the-top show filled with technology, sensory theatrics, comedy, music and hijinks is the perfect form of entertainment. To truly understand the hype over the Blue Man Group in Chicago, you have to see it for yourself! Details
TripAdvisor user rating 4.50 out of 5
1201 Reviews
$71.50 $67.88
Total Price: $69.24 (USD)
You Save: $3.62
Discover a world of creativity, excitement and fun at LEGOLAND® Discovery Center Chicago! Build, play and learn with your family and friends in Chicago’s only two-story LEGO ultimate experience. With 12+ attractions, including a 4D cinema and a jaw-dropping Miniland Chicago cityscape, there’s something for everyone at LEGOLAND in Schaumburg. Details
TripAdvisor user rating 3.50 out of 5
1595 Reviews
$24.99
Total Price: $26.71 (USD)
Chicago Crime Tours offer luxurious 90-minute tours of the Windy City, revealing some of its darker history of infamous criminals and gangsters. Guests can ride comfortably in luxury, climate-controlled bus while learning about Al Capone, John Dillinger, Terrible Tommy, and more, while seeing famous crime scenes, like the Biograph Theatre, Clark Street Bridge, Holy Name Cathedral, and more. Details
TripAdvisor user rating 4.50 out of 5
2785 Reviews
$49.00
Total Price: $55.71 (USD)
An affordable and convenient way to see some of the best attractions Chicago has to offer, the Chicago Explorer Pass offers exclusive discounted rates for up to 30 days after its first use. Guests can enjoy saving up to 35% on several different hotspots, including Adler Planetarium, Field Museum, and Museum of Science and Industry. Details
2 Reviews
$84.00
Total Price: $85.68 (USD)
Located just minutes from the Lincoln Park Conservatory and Old Town Triangle, iFLY Indoor Skydiving Chicago Lincoln Park offers the rush of free-falling in a safe and controlled environment—no airplane or parachute needed. Whether you are a first-timer or a seasoned flyer, expert instructors will guide you through an unforgettable adventure. Come fly today! Details
TripAdvisor user rating 4.50 out of 5
148 Reviews
$89.99
Total Price: $101.67 (USD)
Head out on the Chicago River Dinner Cruise aboard the glass-enclosed Odyssey Chicago River dining vessel to enjoy the heart of Chicago from a unique perspective! Savor a delicious 3-course plated dinner and iconic architectural landmarks such as the Willis Tower, DuSable Bridge, and Merchandise Mart, all beautifully illuminated against the night sky. Details
$198.04
Total Price: $202.00 (USD)
Experience one of the world's greatest museums with an expert tour guide! This skip-the-line guided tour explores major artworks and hidden gems from the expansive Art Institute of Chicago collection, which can be overwhelming to explore on your own. The tour begins half an hour before the museum opens allowing you to stroll among the galleries at a leisurely pace. Details
TripAdvisor user rating 5.00 out of 5
42 Reviews
$132.50
Total Price: $135.15 (USD)
Join the Shoreline Architecture River Cruise from Michigan Avenue and witness the city’s incredible architecture and engineering marvels from the Chicago River! Cruise past over 40 iconic buildings, from the majestic John Hancock Center to the historic Wrigley Building, as your expert guide shares the history of the buildings, their architects and engineers. Details
$53.70 $46.99
Total Price: $52.50 (USD)
You Save: $6.71
Discover as many sites as you can with this All-Inclusive Go City Chicago Pass. With the Chicago Go Pass, you can enjoy a variety of attractions for guests of all ages and interests, including museum admission, theater tours, and sightseeing trips. Save money and plan your adventure through Chicago's urban jungle with this one of a kind passport! Details
1 Reviews
$124.00
Total Price: $126.48 (USD)
Experience the breathtaking Chicago Skyline on a 45-minute Lake Michigan cruise departing from Navy Pier. Enjoy stunning views of the city’s iconic landmarks and skyscrapers such as The Chicago Harbor Lighthouse and Willis Tower, and informative pre-recorded commentary about the history of Chicago’s famous buildings. Don't forget your camera! Details
$37.57 $35.70
Total Price: $39.61 (USD)
You Save: $1.87
This scenic Chicago riverboat tour will surround you with Chicago’s cityscape, modern architecture, and historic buildings. Guided by local experts, passengers learn about Chicago’s vast history, notable citizens, and iconic buildings, including Willis Tower, Aon Center, John Hancock Building, and more. Ideal for the whole family, this cruise is the best way to maximize your time in the city. Details
1 Reviews
$42.00
Total Price: $46.52 (USD)
Experience the Windy City’s iconic sights with a Big Bus Chicago hop on hop off tour and explore the city at your own pace. Enjoy panoramic top-deck views of iconic skyscrapers and Lake Michigan, and hop off to explore the Magnificent Mile, Field Museum, Adler Planetarium, and more. Download the free Big Bus app for routes and real-time tracking. Details
1 Reviews
$55.00
Total Price: $55.55 (USD)
See the Chicago skyline in its full bloom at night from the perspective of the water! This tour will educate and inspire as the boat takes you along Chicago’s river and lakefronts to watch the city dramatically light up for the evening. It’s a memorable trip with exciting views fit for the whole family! Details
1 Reviews
$42.00
Total Price: $46.52 (USD)
Enjoy the beautiful Chicago skyline with spectacular views of Navy Pier's fireworks display! This informative and awe-inspiring trip down the Chicago River will leave you breathless. Learn about the city's history and landmarks from the informative onboard guide. Then enjoy the cityscape and fireworks show with your 3D glasses! Details
1 Reviews
$49.00
Total Price: $54.29 (USD)
Indulge in a premier Chicago dinner cruise aboard Odyssey Lake Michigan. Departing from Navy Pier, pass by iconic landmarks such as Willis Tower, Adler Planetarium, and more. Whether celebrating a special occasion or simply looking for a unique dining experience, this dinner cruise in Chicago offers an unforgettable evening of elegance and fine dining. Details
$188.47
Total Price: $192.24 (USD)
Located minutes from The Morton Arboretum and Arrowhead Country Club, iFLY Naperville offers the ultimate indoor skydiving experience for adventurers of all ages. Soar in a state-of-the-art wind tunnel with expert instructors guiding each flight. No experience necessary—just bring your sense of adventure and prepare for a flight experience of a lifetime. Details
TripAdvisor user rating 4.50 out of 5
275 Reviews
$89.99
Total Price: $91.79 (USD)
Just minutes from O’Hare International Airport and Fashion Outlets of Chicago, iFLY Rosemont offers a thrilling indoor skydiving experience for first-timers and seasoned pros alike. Enjoy a 1.5-hour flying experience in a state-of-the-art vertical wind tunnel, no parachute needed. Let your dreams take flight at iFLY Indoor Skydiving - Chicago Rosemont! Details
TripAdvisor user rating 4.50 out of 5
379 Reviews
$89.99
Total Price: $97.28 (USD)
Set sail on a Chicago lunch cruise for a casual day out on Lake Michigan aboard the Spirit of Chicago. Departing from the iconic Navy Pier, the cruise will pass by iconic landmarks such as the Willis Tower and Adler Planetarium. Feast on a delectable chef-prepared lunch buffet while enjoying stunning views of the Chicago skyline and onboard entertainment. Details
$88.70
Total Price: $90.47 (USD)
Embark the bike tour that’s been recognized by National Geographic, USA Today, and the Associated Press. This leisurely bike tour of Chicago’s Near North Side neighborhoods will captivate you as you view the skyscrapers, visit Lincoln Park, and bike along the Lakefront Trail. Bring a camera along for the ride so you can capture these memories for a lifetime. Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$54.99
Total Price: $61.59 (USD)
In the heart of downtown Chicago, the Writers Museum on Michigan Avenue walks you through centuries of American history and culture from the writers' perspective. The American Writers Museum-Chicago is the only museum devoted to diverse US writers and writings, with fun multi-sensory exhibits to celebrate the past and promote the future of American literature! Details
TripAdvisor user rating 5.00 out of 5
438 Reviews
$16.00
Total Price: $16.32 (USD)
Hop on your bike and get ready for a tasty tour through Chicago’s most diverse and delicious neighborhoods. You’ll stop at local eateries loved by locals all while learning about Chicago’s history, notable landmarks, and restaurants. This four-hour tour includes all food and beverages, along with bikes to ride if you don’t have one. Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$89.99
Total Price: $100.79 (USD)
Get ready to sample Chicago’s iconic food, including deep dish pizza, the original chocolate brownie, and local craft beers. This walking tour brings you around to some of the most renowned restaurants and bars in the city. Along the way, you’ll come across Chicago’s landmarks, well-known neighborhoods, and historic spots. This tour is not recommended for kids under the age of 17. Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$79.99
Total Price: $89.59 (USD)
For authentic cuisine with a rich history, embark on a Chinatown food and walking tour with Bobby’s Bike Hike, America’s longest running city bike tour company. As you stroll through Chinatown’s neighborhoods on this 2.5-hour tour, you’ll sample Cantonese dim sum and tea, try Portuguese-Chinese baked goods, and so much more. Plus, you’ll learn about the history behind the cuisine and culture. Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$79.99 $74.99
Total Price: $83.99 (USD)
You Save: $5.00
Operated by Bobby’s Bike Hike, America’s longest running city bicycle tour company, this 2.5-hour bike tour brings you around to Chicago’s greatest landmarks and sights. You’ll see everything from Museum Campus to Cloud Gate, and Grant Park to Buckingham Fountain. If you’re looking to maximize your time in Chicago while staying active, this is the perfect tour for your trip. Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$54.99
Total Price: $61.59 (USD)
There’s nothing more magical than Chicago during the holiday season. Embark on a walking tour through Chicago’s most festive neighborhoods and restaurants. Sample the city’s best pizza while marveling at sights and decorations along the Magnificent Mile, strolling through Christkindlmarket, and sipping on the Windy City’s best craft beer. It’ll be a holiday season unlike any other! Details
TripAdvisor user rating 5.00 out of 5
4576 Reviews
$79.99
Total Price: $81.59 (USD)
Visit Medieval Torture Museum Chicago and discover the most extensive Middle Ages torture exhibits in the U.S. Located in the Chicago Loop, explore the interactive museum’s elaborate torture devices and realistic execution depictions that are not for the faint of heart! Do you have the courage to endure a visit to the horrifying evidence of human cruelty? Details
1 Reviews
$33.59
Total Price: $38.19 (USD)
Bring your pooch sightseeing on Mercury's Canine Cruise, a dog-friendly boat tour in Chicago! The breathless sights, cool breeze, and educational commentary will keep you entertained as you take the city from the perspective of the river and lakefronts. There's truly nothing like cruising on the water with your best friend! Details
1 Reviews
$44.00 $42.00
Total Price: $46.71 (USD)
You Save: $2.00
Step into the lives of Chicago’s most notorious criminals as you embark on this nighttime tour. From the comfort of an air-conditioned bus, you’ll encounter iconic crime scenes and historic bars. Drinks are not included. On this 2.5-hour luxury bus tour through the streets of Chicago, you’ll learn about everything from the legendary Al Capone to the St. Valentine’s Day Massacre. Details
TripAdvisor user rating 4.50 out of 5
2785 Reviews
$55.00
Total Price: $62.54 (USD)
See Chicago from the ground up and from way up high on this private Chicago walking tour! Discover more about The Windy City while taking advantage of all the city has to offer– including the expansive trails of Millennium Park, the opulent stores on Magnificent Mile, unique art and architecture that defines the city, and a stunning view of the Chicago skyline. Details
TripAdvisor user rating 5.00 out of 5
1 Reviews
$274.00
Total Price: $279.48 (USD)

Visiting the Windy City offers a wide range of things to do in Chicago. Delight in the vibrant, diverse neighborhoods, each with a distinct character and cultural background. With such a rich diversity, the possibilities of what you can do here are virtually endless. Irrespective of the time of year or your interest, the city's versatility ensures something for everyone.

Award winning jazz and blues music is an integral part of Chicago's soul. Without even seeking it out, street musicians' melodies will find their way into your ears, evoking an atmosphere that captures the city's spirit. If architecture piques your interest, then venture on an enlightening walking tour around the city. The blend of historic and modern constructions showcases the city's beautiful evolution over time.

Sports enthusiasts will feel right at home in Chicago. Whether it's cheering on the Cubs at Wrigley Field or the Bulls and Blackhawks at the United Center, the city's devotion to its sports teams is infectious. Alternatively, experience the joy of sailing on Lake Michigan, where the city skyline transforms into an enchanting backdrop.

And what would the lineup of Chicago things to do without tasting its renowned culinary delights? From the famous deep-dish pizza to a diversity of global cuisines, your taste buds are in for a treat. Running parallel to food and architecture, Chicago's art scene is a beacon for those with a keen eye for visual storytelling.


  • Explore the city's diverse neighborhoods, each with a distinct character

  • Indulge in iconic culinary delights, including the famed deep-dish pizza

  • Participate in the vibrant sports scene, with options from baseball to sailing

  • Engage in an insightful architectural tour showcasing Chicago's dynamic evolution


Embrace the city's tempting allure, its infectious music, remarkable architecture, tantalizing cuisine, engaging sports scene, and riveting art – it's all part of the authentic things to do in Chicago.

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