Top Chicago Tours, Sightseeing & Cruises
Saved to wishlist!
When are you traveling?
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.
You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎
Coffee Cruises
Day Cruises
Dinner Cruises
Lunch Cruises
Night Cruises
Ports of Call Tours
Sailing
Shore Excursions
Sightseeing Cruises
Sunset Cruises
Bike Rentals
Bike Tours
Bus Tours
Car Tours
Classic Car Tours
E-Bike Tours
Helicopter Tours
Luxury Car Tours
Mountain Bike Tours
Rail Tours
Rentals
Segway Tours
Self-guided Tours & Rentals
Speed Boats
Walking Tours
Water Tours
Adventure Tours
City Tours
Hop on Hop Off
Night Tours
Observation Decks
Private Sightseeing Tours
Sightseeing Cruises
Sightseeing Passes
Skip-the-Line Tours
Skyscrapers & Towers
Day Trips
Full-day Tours
Half-day Tours
Multi-day Tours
Price
Duration
Time of Day
RatingClear
Specials
Select Dates
171 results | All Chicago Tours
Sort by: Featured
Chicago Architecture River Cruise
6405
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More
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).
…More
* A traveler said: "Great tour with outstanding guide who made the experience memorable with interesting stories and facts."
90-Minute Chicago River Architecture Tour
1115
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* A traveler said: "Awesome experience! Our host was funny, knowledgeable and very personable. He certainly knows his Chicago history!"
Gangsters and Ghosts Tour in Chicago
1914
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
Learn More
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.
…More
* 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 City Minibus Tour with Optional Architecture River Cruise
426
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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!"
Big Bus Chicago Hop-On Hop-Off Tour
865
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More
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.
…More
* 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
1037
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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
483
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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"
45-Minute Chicago River Architecture Tour from Magnificent Mile
127
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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."
Lake Michigan Sightseeing Cruise
303
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More
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.
…More
* A traveler said: "Really nice. Just the right amount of time for this cruise. It was clean and the staff was friendly."
Chicago Favorites Ultimate Food & Walking Tour
250
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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 in a Day: Food, History and Architecture Combo Tour
125
Social distancing enforced throughout experience
Guides required to regularly wash hands
Paid stay-at-home policy for staff with symptoms
Learn More
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.
…More
* A traveler said: "Very knowledgeable guide. An interesting and educational tour. Kelly did a great job showing us Chicago"
Underground Donut Tour: Chicago's First Donut Tour
281
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More
From
$30.00
From
$30.00
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.
…More
* A traveler said: "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!!!"
From
$59.00
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.
…More
* A traveler said: "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"
Chicago Night Crimes Bus Tour
98
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* A traveler said: "Katie was very informative and entertaining. Enjoyed seeing the neighborhoods we went through and many restaurants."
Big Bus Chicago Night Tour
64
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Learn More
From
$29.00
From
$29.00
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
* A traveler said: "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!"
Chicago Premier Dinner Cruise on Lake Michigan
141
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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"
Chicago Pizza Tour
233
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More
From
$60.00
From
$60.00
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
* A traveler said: "Very knowledgeable!!! Guide was fun and enthusiastic! All the four was good and the staff was friendly. I would highly recommend."
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
313
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* 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 Center River Cruise aboard Chicago's First Lady
496
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
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.
…More
* A traveler said: "Patricia was incredible...informative n immensely knowledgable..witty n entertaining. Best tour on the Chicago River!!"
From
$35.00
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.
…More
* A traveler said: "The best part was when it started to get dark and the city was so bright! And of course the yummy drinks!"
Chicago Loop Secret Food Tour with Private Tour Option
253
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
From
$84.53
From
$84.53
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.
…More
* A traveler said: "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."
Chicago's Ultimate City Bike Tour
50
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
From
$49.99
From
$49.99
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.
…More
* A traveler said: "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!"
Lonely Planet Experiences: River North Historical Food Tour
13
Social distancing enforced throughout experience
Guides required to regularly wash hands
Paid stay-at-home policy for staff with symptoms
Learn More
From
$60.96
From
$60.96
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.
…More
* A traveler said: "This was a pretty goo tour, would have liked more food options to try. Our tour guide Wallach was amazing!"
Chicago City Minibus Tour
47
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More
From
$39.00
From
$39.00
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
* A traveler said: "Saw such interesting things in Chicago. Our guide was very informative. We were allowed to stop several times for pictures. Enjoyed seeing old neighborhoods."
* How are review snippets generated?
- Wrigley Building
- Chicago Lakefront Trail
- Chicago Riverwalk
- Lincoln Monument
- American Writers Museum
- Lincoln Park Conservatory
- Chicago Loop
- Wrigley Field
- Grant Park
- Chicago Children's Museum
- Chicago Board of Trade Building
- Second City
- Harold Washington Library Center (Chicago Public Library)
- Northerly Island
- Rookery Building
- Medieval Times Chicago
- Biograph Theater
- Jackson Park
- Navy Pier
- Pizzeria Uno
- Things to do in Illinois
- Things to do in Nashville
- Things to do in Pittsburgh
- Things to do in Toronto
- Things to do in Niagara Falls & Around
- Things to do in Niagara Falls
- Things to do in Buffalo
- Things to do in Branson
- Things to do in Greenville
- Things to do in Atlanta
- Things to do in Washington DC
- Things to do in Ontario
- Things to do in Missouri
- Things to do in Tennessee