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60 results | All Chicago Tours

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Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6405
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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* A traveler said: "Great tour with outstanding guide who made the experience memorable with interesting stories and facts."


90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1115
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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* A traveler said: "Awesome experience! Our host was funny, knowledgeable and very personable. He certainly knows his Chicago history!"


Chicago Sunset Cruise
Likely to Sell OutLikely to Sell Out

Chicago Sunset Cruise

star-4.5
137
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
The Sunset Cruise departs from the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. Enjoy the beautiful City architecture from the best vantage point in Chicago. The vessel will then navigate through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.
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* A traveler said: "So beautiful and peaceful. We will definitely visit and do this again. The view was breathtaking. Love!"


360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
298
  • 1 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$41.50
From
$41.50
Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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* A traveler said: "Cool to be at the top as the sun went down. Got to see the city during the day and ar night! Must do"


Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1914
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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* A traveler said: "Lizzie was very informative, fun, and personable. I enjoyed hearing stories about Chicago I’d never heard before and seeing the fabulous Palmer Hotel."


Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
483
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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* A traveler said: "Great tour, great knowledge and great views! Enjoyed the bar down stairs and AC as a. Option to stay outside the sun"


Chicago Architectural River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architectural River Cruise

star-4.5
704
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$49.05
From
$49.05
See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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* A traveler said: "Knowledgeable & professional staff. The buildings were unbelievable and the history lesson was great."


Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
303
  • 40 minutes
  • Free Cancellation
  • Taking safety measures
From
$27.25
From
$27.25
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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* A traveler said: "Really nice. Just the right amount of time for this cruise. It was clean and the staff was friendly."


Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
865
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$26.10
From
$26.10
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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* A traveler said: "All of it. Ricardo was engaging and provided helpful tidbits. The ride was comfortable and safe. I would do it again."


Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1037
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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* A traveler said: "The history learned was really cool. Tour guide Mike was very knowledgeable and fun. My kids enjoyed as well"


30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

star-4.5
110
  • 30 minutes
  • Taking safety measures
From
$34.75
From
$34.75
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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* A traveler said: "The water, buildings and weather. The information was great! When the water sprinkled in me. The speaker, captain and all the above was a great experience. I would definitely do it again."


Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

star-5
22
  • 1 hour 15 minutes
  • Taking safety measures
From
$92.64
From
$92.64
Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.
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* A traveler said: "The instructor was amazing I would most definitely come back and my hunny is afraid of highest and made her feel comfortable"


Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

star-4
11
  • 1 hour 15 minutes
  • Taking safety measures
From
$86.69
From
$86.69
Discover the adrenaline rush of skydiving without setting foot on a plane at iFly Chicago-Rosemont. Offered 9am to 10pm, you can easily find a session that fits with your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats.  An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.
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* A traveler said: "The flight instructors were amazing. They made the experience fun for all. If you are in the mood for something different, this is an event everyone should experience at least once."


Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

star-5
1
  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$295.00
per group
From
$295.00
per group
Aviation fanatics can take to the skies and try flying an actual helicopter with this Schaumburg flight experience that's perfect for first-timers. You enjoy helpful advice from your instructor before taking the controls on a flight that whisks you past Sears Centre Arena, Woodfield Mall, and Boomers Stadium. With free parking, noise-canceling headphones, and one-on-one attention from the pilot, this beginner-friendly experience is a near-perfect way to try flying for yourself.
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* A traveler said: "Yes, Sarah was an AWESOME instructor and a pleasure to meet. She gave me the best experience of my life flying in the air with the scenic view of the Chicago building, airport, and the lake. I highly recommend this experience to others. BEAUTIFUL."


Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
496
  • 1 hour 30 minutes
  • Taking safety measures
From
$56.00
From
$56.00
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
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* A traveler said: "Patricia was incredible...informative n immensely knowledgable..witty n entertaining. Best tour on the Chicago River!!"


Chicago CityPASS

Chicago CityPASS

star-4.5
333
  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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* A traveler said: "The city pass is great to get into some of the highlights of Chicago. The museums are a day event to see all the amazing displays. The Willis tower and Chicago 360 give some great views and I’m looking forward to seeing the aquarium next!"


Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
313
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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* A traveler said: "The highlight of our trip to Chicago. So much fun. Julia was the best tour guide ever. The stops foe Brews and Bites were amazing."


Chicago Architecture Boat Tour
Likely to Sell OutLikely to Sell Out

Chicago Architecture Boat Tour

star-5
300
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$32.00
From
$32.00
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. The Chicago River Cruise navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island and the south branch to Chinatown.
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* A traveler said: "Our guide talked the whole 1 1/2 hours without a note! He knew so much information about the buildings we saw, and told stories instead of dry facts. Superb!"


Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
143
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
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* A traveler said: "This was a very nice tour of some of the best spots in Downtown Chicago. Lake was so friendly and informative. Definitely put this on your list the next time you are in Chicago."


Chicago Premier Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
141
  • 2 hours 30 minutes
  • Taking safety measures
From
$158.98
From
$158.98
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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* A traveler said: "The observation deck was very nice, especially since it was a beautiful night. Also the fireworks were a nice touch at the end"


45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
127
  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$23.00
From
$23.00
Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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* A traveler said: "Did the night time tour. It was stunning. Cool history on the buildings too. 1/2 way through you get the most beautiful and breathtaking view of the skyline all lit up In the night."


Chicago Urban Adventure River and Lake Cruise

Chicago Urban Adventure River and Lake Cruise

star-4.5
111
  • 1 hour 30 minutes
  • Free Cancellation
From
$39.00
From
$39.00
See the the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline. Take in towering skyscrapers and spot the gargoyles that live on to of the city’s historic buildings. Hear stories about the city’s history and culture as you pass Chicago landmarks, museums and iconic buildings. Capture unforgettable images of the city skyline from Lake Michigan, and get a unique look at Chicago that’s perfect for all ages.
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* A traveler said: "Being out on lake Michigan, seeing the beautiful skyline, the tour guide Sarah was fun and informative!"


Chicago Lunch Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Lunch Cruise on Lake Michigan

star-4
81
  • 2 hours
  • Taking safety measures
From
$81.46
From
$81.46
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
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* A traveler said: "The food was delicious great atmosphere will definitely be back . Customer service was top notch will definitely be back"


Chicago's West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour

star-5
79
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$79.99
From
$79.99
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
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* A traveler said: "Gabe was a terrific guide on our bike tour. He was very funny & super friendly. Loved all the neighborhoods we rode through, and the food was amazing! I’d highly recommend it!"


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The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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What Outdoor Activities in Chicago are 1 hour or less?
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