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92 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!"


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 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"


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"


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 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!"


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 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."


Field Museum of Natural History Admission Tickets
Likely to Sell OutLikely to Sell Out

Field Museum of Natural History Admission Tickets

star-4.5
145
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
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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* A traveler said: "What a wonderful, educational experience! We thoroughly enjoyed touring the museum and leisurely exploring different exhibits. The mammals exhibit and Nature Walk were especially well designed and the animals looked as through they could be living and breathing in their glass enclosures. It was absolutely fantastic!"


Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-5
426
  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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* A traveler said: "The tour was excellent! Rick was funny, witty. Knowledgeable about the city. He knew both historical and Pop culture. The short stops were perfect! I have been traveling for the last 3 weeks to various city for my bday and I did not want to go on another tour. But I am glad I did! PS.. I am a Philly girl so not easily impressed!"


Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
250
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$65.99
From
$65.99
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. Upgrade your tour to include three pours of local craft beer.
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* A traveler said: "Our tour guide, Brooke, was fabulous! She was very knowledgeable and entertaining. I would definitely recommend this day tour. Lots of fun and lots of food!!"


Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
267
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$33.00
From
$33.00
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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* A traveler said: "Hillary did a great job showing us an out of the path Chicago. She is very knowledgeable of Chicago with focus in history and architecture. The selection of places gave us an amazing experience through styles and time. We highly recommend this tour! Thank you Hillary!"


2-Hour Chicago Lakefront and Museum Campus Segway Tour
From
$73.24
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.
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* A traveler said: "Good segways and a great guide (Tammy).. you won’t regret taking this tour.. wear comfy shoes or your feet will curse you by the end"


Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
145
  • 2 hours
  • Free Cancellation
From
$73.24
From
$73.24
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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* A traveler said: "It was the funniest way to see Chicago. The Segway girl, named Tammy, is the best. Ride a Segway is very easy, even for child’s."


Chicago Private Tours

Chicago Private Tours

star-5
142
  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$425.34
per group
From
$425.34
per group
Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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* A traveler said: "We loved how knowledgeable our tour guide was. He had so much information about the city. We really enjoyed driving around the city."


2-Hour Guided Segway Tour of Chicago
Likely to Sell OutLikely to Sell Out

2-Hour Guided Segway Tour of Chicago

star-5
121
  • 2 hours
  • Free Cancellation
From
$65.00
From
$65.00
Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.
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* A traveler said: "Captain Segway made our first Segway experience a great one! My wife was very hesitant about climbing on a Segway but Mike was able to provide her the confidence to drive around by helping her through the tour. At the end, she was proud of her accomplishment and we were able to enjoy Chicago on a beautiful Summer day. Thank you Mike!"


Chicago in a Day: Food, History and Architecture Combo Tour
Likely to Sell OutLikely to Sell Out

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

star-5
125
  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$104.00
From
$104.00
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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* A traveler said: "Very knowledgeable guide. An interesting and educational tour. Kelly did a great job showing us Chicago"


Chicago Night Crimes Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Night Crimes Bus Tour

star-4.5
98
  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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* A traveler said: "Katie was very informative and entertaining. Enjoyed seeing the neighborhoods we went through and many restaurants."


Offbeat Chicago Food Tour: Go Deeper Than Deep Dish

Offbeat Chicago Food Tour: Go Deeper Than Deep Dish

star-5
95
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$70.00
From
$70.00
Savor the flavors of Chicago — the ‘City of Neighborhoods’ — on a guided, ethnic food tour. This 3.5-hour adventure explores two of Chicago's most diverse neighborhoods: Argyle and Andersonville on the city’s North Side. Sample seven distinctly different types of food, visit landmark locations and learn about the local history and culture.
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* A traveler said: "We had such a great time on this tour! We've been to Chicago many times, but never would have ventured to these cute little neighborhoods. All the food was outstanding, the history was entertaining, and the local venues were worth revisiting. Can't recommend this tour highly enough!"


Chicago Walking Tour: Art Deco Skyscrapers
Likely to Sell OutLikely to Sell Out

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
78
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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* A traveler said: "David took us to a trip to the past. Art Deco can be hidden or glowing in front of you and David gave us tips on how to recognize it. He took us to amazing places around Downtown where this style exists. Thank you for sharing with us! We highly recommend this tour!"


Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

star-4.5
63
  • 1 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
One of Chicago’s most popular and recognizable landmarks, the Field Museum of Natural History offers a wide array of treasures, from its Hall of Gems to Sue—one of the best-preserved Tyrannosaurus Rex fossils ever found. Guarantee your admission to this in-demand museum, and prevent any stress, by booking your tickets before you travel. Upon arrival, you can explore the museum at your own pace, and even embark on a complimentary, docent-led tour.
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* A traveler said: "Loved it. We ran out of time to see everything even starting at 11am-5pm. We will definitely be visiting again!"


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