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Skydeck Chicago

Downtown, Chicago
Located on the 103rd floor of the former Sears Tower, Skydeck Chicago offers a unique way to see The Windy City and beyond from a jaw-dropping 1,353 feet in the air. Open 365 days a year, this exciting attraction also offers museum-quality exhibits, a fascinating theater presentation and more. Guests can step out on The Ledge’s glass boxes, which extend about 4.3 feet from the Skydeck. Details
TripAdvisor user rating 4.50 out of 5
17625 Reviews
$25.00 $20.00
You Save: $5.00

360 CHICAGO

Downtown, Chicago
Ever wondered what the entire city of Chicago looked like from 1,000 feet up? Located on the 94th floor of the John Hancock Center, you can see captivating views of Chicago and Lake Michigan. If you’re daring, try TILT — a one-of-a-kind attraction that angles visitors 30 degrees over Michigan Avenue for an unbeatable view. Trust us, this exhilarating opportunity is worth it! Details
TripAdvisor user rating 4.50 out of 5
10663 Reviews
$21.43

Blue Man Group Chicago

Briar Street Theatre • Chicago, Northern Illinois
To say that the bald, brilliant, and hilarious Blue Man Group marches 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 for the entire family. To truly understand the hype over the Blue Man Group, you have to see it for yourself! Details
TripAdvisor user rating 4.50 out of 5
1119 Reviews
$69.50 $54.50
You Save: $15.00
Cruise around Lake Michigan or see Chicago’s famous and historic architecture with Shoreline Sightseeing. No matter which cruise experience you choose, you’re in for an exciting time. Tours include professional narration, snacks and beverages available for purchase, and unparalleled views of Chicago. Each touring vessel has been custom crafted to ensure the safety and security of passengers. Details
TripAdvisor user rating 5.00 out of 5
5169 Reviews
$39.00 $36.56
You Save: $2.44
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 a 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
1003 Reviews
$36.24
Climb aboard a state-of-the-art helicopter and get ready to see the Windy City from an entirely new perspective. Soar high above the city in a daytime, evening, or twilight tour for remarkable views of the Chicago cityscape. Watch the city shine below while you learn about city landmarks, history, notable events, and more. Details
TripAdvisor user rating 4.50 out of 5
473 Reviews
$159.99
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
1003 Reviews
$40.82

Adler Planetarium

Downtown, Chicago
Located in Chicago, Illinois, Adler Planetarium serves as America’s first planetarium and prime resource for inspiring future space explorers. Guests can enjoy seeing the various exhibitions (including Mission Moon, Our Solar System, Telescopes: Through the Looking Glass and more), shows (like Imagine the Moon, Destination Solar System, Skywatch Live and more), programs and more. Details
TripAdvisor user rating 4.00 out of 5
2089 Reviews
$28.00

Art Institute of Chicago

Downtown, Chicago
Boasting more than 1.5 million local, national, and international visitors a year, the Art Institute of Chicago is a must-see destination. Located at 111 South Michigan Avenue in the World’s Fair Building, the Art Institute is home to a world-class collection of fine art ranging from contemporary pieces to historic works of art such as Pablo Picasso’s, “The Old Guitarist” and Grant Wood’s, “American Gothic.” Details
TripAdvisor user rating 5.00 out of 5
23676 Reviews
$35.00 $33.00
You Save: $2.00
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 40% on several different hotspots, including Adler Planetarium, Art Institute of Chicago, Field Museum and Museum of Science and Industry. Details
$135.00 $81.00
You Save: $54.00

Historic Chicago Walking Bar Tour

Chicago Detours • Chicago, Northern Illinois
Presented by Chicago Detours, Historic Chicago Walking Bar Tour offers a 2.5-hour experience sampling some of the area’s best eats and drinks, seeing the beautiful architecture and learning about its history from the Prohibition era. Highlights include Tribune Tower, the famous Billy Goat Tavern, a 19th-century mansion, a former historic jazz club and speakeasy, Magnificent Mile and more. Details
TripAdvisor user rating 5.00 out of 5
688 Reviews
$36.00
Immerse your family into one-of-a-kind LEGO® exhibits, rides, 4D theaters, and so much more at the LEGOLAND® Discovery Center in Chicago. Tour the LEGO® factory, ask a pro builder all of your questions, and build to your heart’s desire! From the DUPLO Village to MINILAND Chicago, there’s so much to explore. With 11+ attractions to enjoy, it’s fun for the whole family. Details
TripAdvisor user rating 3.50 out of 5
1513 Reviews
$20.50 $17.49
You Save: $3.01

1893 World's Fair Tour with Bars

Chicago Detours • Chicago, Northern Illinois
Presented by Chicago Detours, 1893 World’s Fair Tour with Bars and Food offers a three-hour experience that’s broken up into 95% indoors and 5% outdoors. Tour highlights include seeing the grand lobby of the Auditorium Building, tasting mouth watering German food at the Berghoff Restaurant, a secret alley building, one of the last elevators with a human operator in downtown Chicago and more. Details
TripAdvisor user rating 5.00 out of 5
688 Reviews
$42.00
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
3483 Reviews
$82.49
Operated by Bobby’s Bike Hike, this comedy walking tour will make your sides hurt from so much laughing! Spend 2.5 hours exploring Chicago’s Old Town neighborhood where you’ll visit a comedy club, sample local craft beer, and learn more about the area’s history. Due to the nature of this tour, only guests ages 21 and up are permitted to participate. Details
TripAdvisor user rating 5.00 out of 5
3483 Reviews
$67.75

Chicago Day Bike Tours

Fat Tire Tours • Chicago, Northern Illinois
Hop on a bike and pedal from Grant Street to Lincoln Park! This tour takes you through eight prestigious neighborhoods and makes numerous stops for incredible photo opportunities. You will hear the history of Chicago from a knowledgeable guide as you appreciate the stunning city architecture and beautiful lakefront. This tour is a fantastic way to see Chicago’s most famous sites! Details
TripAdvisor user rating 5.00 out of 5
9 Reviews
$43.39

Chicago Evening Segway Tour

City Segway Tours • Chicago, Northern Illinois
Enjoy the thrill of riding a Segway while observing the beautiful sunset over Chicago’s most famous sites including Grant Park, Buckingham Fountain, Lake Michigan Lakefront. and the Museum Campus. A knowledgeable guide will keep you on your toes with fun facts and history along the way. The city skyline at nightfall is truly a spectacle to behold! This experience is a great way to spend an evening with friends and family. Details
TripAdvisor user rating 5.00 out of 5
928 Reviews
$70.85
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
3483 Reviews
$63.21

Chicago Fireworks Segway Tour

City Segway Tours • Chicago, Northern Illinois
Hop on a Segway and glide to an exclusive viewing location for the Navy Pier's famous evening fireworks show. Not only will you beat the crowds and have a perfect vantage point, but you will also get a sightseeing experience on the way. Visit Buckingham Fountain, the Lake Michigan Lakefront, Monroe Harbor, and many other famous sites. Once the show is over, your guide can help you find the perfect nightcap. Details
TripAdvisor user rating 5.00 out of 5
928 Reviews
$76.30

Chicago Odyssey

Entertainment Cruises • Downtown, Chicago
An unforgettable dining cruise over Lake Michigan, Chicago Odyssey offers a scenic escape from land to see The Windy City’s breathtaking skyline from the sea. Guests can enjoy all that the ship has to offer, including three climate-controlled decks with a dance floor and LED lighting, a wide range of wine and microbrew selections, a delicious dinner, and a rooftop lounge with modern furniture. Details
TripAdvisor user rating 4.50 out of 5
34 Reviews
$101.86 $89.12
You Save: $12.74

Chicago Sunset Bike Tour

Fat Tire Tours • Chicago, Northern Illinois
Enjoy a leisurely bike ride through the city as the daylight dips below the horizon on the Chicago Sunset Bike Tour! You will see iconic sites like never before as beautiful setting rays create a colorful display of light. This sightseeing experience offers incredible Skyline views and visits many hidden gems of the city. Riding a bike is the most pleasant way to travel around Chicago and is fun for all ages! Details
TripAdvisor user rating 5.00 out of 5
9 Reviews
$42.51
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
3483 Reviews
$63.21
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
3483 Reviews
$50.74
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
3483 Reviews
$67.75

iFly Lincoln Park

Chicago, Northern Illinois
Located just minutes from Lincoln Park Conservatory, Old Town Triangle and more, iFly Lincoln Park offers an exciting indoor skydiving experience for guests of almost any age to enjoy while visiting The Windy City. This unique attraction lets guests enjoy a one-and-a-half-hour flying experience indoors in a flight chamber without having to use a parachute and without having to jump. Details
TripAdvisor user rating 5.00 out of 5
129 Reviews
$69.95

iFly Naperville

Naperville, Chicago
Located just minutes from The Morton Arboretum, Arrowhead Country Club and more, iFly Naperville offers a thrilling indoor skydiving experience for guests of almost any age to enjoy while visiting the Chicago-Naperville area. This one-of-a-kind attraction lets guests enjoy a one-and-a-half-hour flying experience indoors in a flight chamber without a parachute and without jumping. Details
TripAdvisor user rating 4.50 out of 5
272 Reviews
$69.95

iFly Rosemont

Rosemont - O'Hare Airport, Chicago
Situated just a few minutes from the O’Hare International Airport, Fashion Outlets of Chicago and more, iFly Rosemont offers a thrilling indoor skydiving experience for guests of almost any age to enjoy while visiting the Chicago-Rosemont area. This unique attraction allows guests enjoy a one-and-a-half-hour flying experience in a flight chamber without a parachute and without jumping. Details
TripAdvisor user rating 4.50 out of 5
371 Reviews
$69.95
Presented by Chicago Detours, Loop Interior Architecture Walking Tour offers a unique way to get an in-depth view of downtown Chicago’s beautiful architecture. Guests will see inside a variety of lobbies, corridors, the underground Pedway system and more, with roughly 95% of the tour taking place indoors. Highlights include the “Chicago Picasso” sculpture, Chicago Cultural Center and more. Details
TripAdvisor user rating 5.00 out of 5
688 Reviews
$28.00
Offered by Spirit Cruises, the Spirit of Chicago features a breathtaking experience for guests to view the beautiful Chicago skyline while dining, drinking and dancing at sea. The cruise ship provides a rooftop lounge, three climate-controlled interior decks with stunning panoramic windows, a live DJ and spacious dance floors, full-service bars and a delicious meal fit for any palate. Details
TripAdvisor user rating 4.00 out of 5
436 Reviews
$81.46

The Escape Game Chicago

Chicago, Northern Illinois
You’re trapped in a room with your closest friends and family. There’s 60 minutes on the clock and a world of puzzles to solve before you can escape. Do you think your group can band together to beat the clock? At Escape Game Chicago, you can choose from different themed rooms including a heist scenario and a jailbreak. Use your teamwork and communication skills to beat the challenges and escape! Details
TripAdvisor user rating 5.00 out of 5
2471 Reviews
$35.99 $33.99
You Save: $2.00

Two Hour Chicago Segway Tour

City Segway Tours • Chicago, Northern Illinois
Segway is the newest trend when it comes to touring because you can cover more ground. Plus, it’s just plain fun! You will have numerous Instagram-worthy photo opportunities as you travel to the best spots in Chi-Town including Grant Park, Buckingham Fountain, the Crown Fountain, and so much more! Your knowledgeable guide will reveal interesting facts and history of Chicago along the way. Details
TripAdvisor user rating 5.00 out of 5
928 Reviews
$70.85

Medieval Times Dinner and Tournament Illinois

Medieval Times Dinner and Tournament Chicago/Schaumburg Castle • Schaumburg, Chicago
One of the country’s longest-running dinner attractions, Medieval Times Dinner and Tournament Illinois offers a fun and exciting way to enjoy a meal with family or friends. Guests can enjoy a hearty four-course meal, served banquet-style (without silverware), while watching as six brave knights compete in games of skill atop their beautiful Andalusian stallions. Details
TripAdvisor user rating 4.00 out of 5
934 Reviews
$61.95 $49.94
You Save: $12.01