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171 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
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).
More
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
Taking safety measures

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1115
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1914
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 City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-5
426
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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  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Taking safety measures

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
865
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$26.10
From
$26.10
Taking safety measures

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1037
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 Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
483
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

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
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

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
303
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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  • 40 minutes
  • Free Cancellation
  • Taking safety measures
From
$27.25
From
$27.25
Taking safety measures

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
250
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$65.99
From
$65.99
Taking safety measures

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
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
$104.00
From
$104.00
Taking safety measures

Underground Donut Tour: Chicago's First Donut Tour

Underground Donut Tour: Chicago's First Donut Tour

star-5
281
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4
215
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
$59.00
From
$59.00

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

Chicago Night Crimes Bus Tour

star-4.5
98
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.
More
  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Big Bus Chicago Night Tour

Big Bus Chicago Night Tour

star-4
64
See Chicago's dazzling skyscrapers lit up for the night during this 75-minute Big Bus tour. The entire loop takes passengers from Navy Pier, down the Magnificent Mile to Michigan Avenue, through the Museum Campus and around the architectural gems on the Loop skyline. Live and audio commentary available in English.
More
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$29.00
From
$29.00
Taking safety measures

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
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.
More
  • 2 hours 30 minutes
  • Taking safety measures
From
$158.98
From
$158.98
Taking safety measures

Chicago Pizza Tour
Likely to Sell OutLikely to Sell Out

Chicago Pizza Tour

star-5
233
Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
More
  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.00
From
$60.00
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
313
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.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
496
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.
More
  • 1 hour 30 minutes
  • Taking safety measures
From
$56.00
From
$56.00
Taking safety measures

Chicago River Floating Tiki Bar Cruise

Chicago River Floating Tiki Bar Cruise

star-4
34
See Chicago the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have questions about the buildings you'll see along the river? Our helpful staff will be happy to answer questions.
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  • 1 hour 15 minutes
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

star-5
253
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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  • 3 hours
  • Taking safety measures
From
$84.53
From
$84.53
Taking safety measures

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
50
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

Lonely Planet Experiences: River North Historical Food Tour
Likely to Sell OutLikely to Sell Out

Lonely Planet Experiences: River North Historical Food Tour

star-5
13
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$60.96
From
$60.96
Taking safety measures

Chicago City Minibus Tour

Chicago City Minibus Tour

star-5
47
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 10 people ensures a more personal experience. 
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$39.00
From
$39.00
Taking safety measures

Filters

What people are saying about Tours, Sightseeing & Cruises in Chicago

star-5
Chicago Architecture River Cruise
"Great tour with outstanding guide who made the experience memorable with interesting stories and facts."..."
star-5
90-Minute Chicago River Architecture Tour
"Awesome experience! Our host was funny, knowledgeable and very personable. He certainly knows his Chicago history!"..."
star-5
Gangsters and Ghosts Tour in Chicago
"Lizzie was very informative, fun, and personable. I enjoyed hearing stories about Chicago I’d never heard before and seeing the fabulous Palmer Hotel."..."
star-5
Chicago City Minibus Tour with Optional Architecture River Cruise
"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!"..."
star-5
Big Bus Chicago Hop-On Hop-Off Tour
"All of it. Ricardo was engaging and provided helpful tidbits. The ride was comfortable and safe. I would do it again."..."
star-5
Chicago Crime and Mob Bus Tour
"The history learned was really cool. Tour guide Mike was very knowledgeable and fun. My kids enjoyed as well"..."
star-5
Chicago Lake and River Architecture Tour
"Great tour, great knowledge and great views! Enjoyed the bar down stairs and AC as a. Option to stay outside the sun"..."
star-5
45-Minute Chicago River Architecture Tour from Magnificent Mile
"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."..."
star-5
Lake Michigan Sightseeing Cruise
"Really nice. Just the right amount of time for this cruise. It was clean and the staff was friendly."..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"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!!"..."
star-5
Chicago in a Day: Food, History and Architecture Combo Tour
"Very knowledgeable guide. An interesting and educational tour. Kelly did a great job showing us Chicago"..."
star-5
Underground Donut Tour: Chicago's First Donut Tour
"We loved this tour. The donuts were fantastic, but I have to say it was the community feel that made it special. Walking along, chatting with strangers and learning about the city. It was the perfect Saturday morning!!!"..."
star-5
Go Chicago Explorer Pass with SkyDeck and 360 Chicago
"So fun! The River architecture boat tour was my favorite. We saw the Field Museum as well and it took a whole day to attempt to see it all"..."
star-5
Chicago Night Crimes Bus Tour
"Katie was very informative and entertaining. Enjoyed seeing the neighborhoods we went through and many restaurants."..."
star-5
Big Bus Chicago Night Tour
"Awesome tour! Our guide was funny and informative. We saw great sites! We stopped on Museum Campus for a night time city sky line photo opt. It was the best thing we did while in Chicago! Highly recommend!"..."
star-5
Chicago Premier Dinner Cruise on Lake Michigan
"The observation deck was very nice, especially since it was a beautiful night. Also the fireworks were a nice touch at the end"..."
star-5
Chicago Pizza Tour
"Very knowledgeable!!! Guide was fun and enthusiastic! All the four was good and the staff was friendly. I would highly recommend."..."
star-5
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
"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."..."
star-5
Chicago Architecture Center River Cruise aboard Chicago's First Lady
"Patricia was incredible...informative n immensely knowledgable..witty n entertaining. Best tour on the Chicago River!!"..."
star-5
Chicago River Floating Tiki Bar Cruise
"The best part was when it started to get dark and the city was so bright! And of course the yummy drinks!"..."
star-5
Chicago Loop Secret Food Tour with Private Tour Option
"Deanise was very nice and knowledgeable. It felt like walking with. Friend from Chicago versus someone paid to show us around . The food places where delicious , would recommend taking this tour."..."
star-5
Chicago's Ultimate City Bike Tour
"Love doing bike tours at the beginning of a trip to orient myself with a city - this was a great way to see Chicago and get some history. Did this tour with my adult daughter and we really enjoyed it. Our guide, Gabe, was funny, engaging and informative. Highly recommend!"..."
star-5
Lonely Planet Experiences: River North Historical Food Tour
"This was a pretty goo tour, would have liked more food options to try. Our tour guide Wallach was amazing!"..."
star-5
Chicago City Minibus Tour
"Saw such interesting things in Chicago. Our guide was very informative. We were allowed to stop several times for pictures. Enjoyed seeing old neighborhoods."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Tours, Sightseeing & Cruises in Chicago?
Q:
What Tours, Sightseeing & Cruises in Chicago are taking additional safety precautions?
Q:
What Tours, Sightseeing & Cruises in Chicago are good for avoiding crowds?