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Chicago Tours

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Chicago Day Cruises
Chicago Day Cruises 29 Tours & Activities
360 Chicago Observation Deck  Tours
360 Chicago Observation Deck Tours12 Tours & Activities
Chicago River and Lake Michigan Cruises
Chicago River and Lake Michigan Cruises10 Tours & Activities
Willis Tower  Tours
Willis Tower Tours30 Tours & Activities

280 results

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
4772
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). From Memorial Day to Labor Day (May 29 - September 6,) each ticket includes a one-way water taxi ticket.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.15
From
$38.15
Taking safety measures

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
502
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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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$39.00
From
$39.00
Taking safety measures

360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
252
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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  • 1 day
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1275
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Chicago CityPASS

Chicago CityPASS

star-4.5
303
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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  • 9 days
From
$109.00
From
$109.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4
758
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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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-4
66
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$111.38
From
$111.38
Taking safety measures

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

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

star-5
243
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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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
110
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

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

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

star-5
13
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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  • 1 hour 15 minutes
  • Taking safety measures
From
$92.64
From
$92.64
Taking safety measures

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
213
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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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$39.00
From
$39.00
Taking safety measures

45-Minute Chicago River Architecture Tour from Magnificent Mile

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-5
46
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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  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$23.00
From
$23.00
Taking safety measures

Chicago in a Day: Food, History and Architecture Combo Tour

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
65
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$102.30
From
$102.30
Taking safety measures

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
150
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$62.99
From
$62.99
Taking safety measures

Chicago Lunch Cruise on Lake Michigan

Chicago Lunch Cruise on Lake Michigan

star-4.5
33
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$81.46
From
$81.46
Taking safety measures

Spray Paint 'n' Sip at Studio W.I.P.

Spray Paint 'n' Sip at Studio W.I.P.

star-4.5
13
Native 312 offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Urban Art as we learn about some different styles and techniques with guest artists. Then you get your hands dirty as you walk around our gallery setting and test out your skills in different mediums like aerosol spray and stencil. At the end of your workshop you will be able to go home with your own piece of art!
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

star-5
4
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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  • 1 hour 15 minutes
  • Taking safety measures
From
$86.69
From
$86.69
Taking safety measures

Premier Chicago River Dinner Cruise

Premier Chicago River Dinner Cruise

star-3.5
3
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
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  • 3 hours
  • Taking safety measures
From
$172.58
From
$172.58
Taking safety measures

Tandem Skydiving Experience in Chicago

Tandem Skydiving Experience in Chicago

star-5
29
Go skydiving in Indiana at a location situated only a 1-hour train ride from Chicago, making it easy to reach without a car. Your instructor provides all necessary equipment and training for your jump, then accompanies you on the tandem skydiving experience from 14,000 feet (4,267 meters). See Lake Michigan and perhaps the Chicago skyline from the air, and purchase video and photos of your jump if you wish.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$209.00
Price varies by group size
From
$209.00
Price varies by group size
Taking safety measures

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
38
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
129
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

2-Hour Guided Segway Tour of Chicago

2-Hour Guided Segway Tour of Chicago

star-5
65
2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!
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  • 2 hours
  • Free Cancellation
From
$65.00
From
$65.00

Chicago Family Food & Bike Tour with Top Attractions

Chicago Family Food & Bike Tour with Top Attractions

star-5
35
See Chicago light up with a 4-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, Italian beef, and a tasty dessert for good measure. Upgrade your experience to enjoy a locally crafted beer pairing at three of the food stops. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$79.99
From
$79.99
Taking safety measures

Chicago's West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour

star-5
69
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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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$79.99
From
$79.99
Taking safety measures

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