Recent Searches
Clear

Top Chicago Tours by Duration

Saved to wishlist!
Dates
Select Dates
Architecture Tours
Architecture Tours
Half-day Tours
Half-day Tours
Hop on Hop Off Buses
Day Cruises
Day Cruises
Cruises & Sailing
Cruises & Sailing
City Tours
City Tours
Historical Tours
Historical Tours
Private and Luxury
Private and Luxury
Private Sightseeing Tours
Private Sightseeing Tours
Audio Guides
Audio Guides
Food Tours
Food Tours
Sightseeing Passes
Sightseeing Passes
Multi-day Tours
Full-day Tours
Full-day Tours
Sunset Cruises
Sunset Cruises
Crime Tours
Crime Tours
Bus Tours
Bus Tours
Dinner Cruises
Dinner Cruises
Water Tours
Water Tours
Walking Tours
Walking Tours
When are you travelling?
Select Dates
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. 🌎

Price
USD0
USD500+
Duration
Time of Day
RatingClear
Specials

80 results | All Chicago Tours

Revenue may affect this sort orderWhy you are seeing these results Sort by: Featured

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
479
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
  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
166
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.
More
  • 3 hours
  • Free Cancellation
From
USD54.99
From
USD54.99

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

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

star-5
388
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 Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. 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
From
USD89.99
From
USD89.99

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown Food and Walking Tour

star-4.5
87
Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
More
  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
74
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
  • 3 hours
  • Free Cancellation
From
USD54.99
From
USD54.99

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1135
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
  • 2 hours
  • Free Cancellation
From
USD44.99
From
USD44.99

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8579
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
From
USD46.87
From
USD46.87

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1529
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
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
USD46.00
From
USD46.00

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2240
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
From
USD42.00
From
USD42.00

Chicago Small-Group City Tour with Optional Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Small-Group City Tour with Optional Architecture River Cruise

star-5
521
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
  • 2 to 4 hours
  • Free Cancellation
From
USD43.95
From
USD43.95

360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
332
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.
More
  • 1 to 4 hours
  • Free Cancellation
From
USD30.00
From
USD30.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2937
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
  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
456
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this 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
  • 40 minutes
  • Free Cancellation
From
USD28.34
From
USD28.34

Chicago Night Crimes Bus Tour

Chicago Night Crimes Bus Tour

star-5
180
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
From
USD52.00
From
USD52.00

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
877
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
From
USD42.00
From
USD42.00

Chicago Sunset Cruise
Likely to Sell OutLikely to Sell Out

Chicago Sunset Cruise

star-4.5
389
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
USD40.00
From
USD40.00

Chicago Craft Brewery Barrel Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Craft Brewery Barrel Bus Tour

star-5
100
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
More
  • 3 hours 45 minutes
  • Free Cancellation
From
USD99.60
From
USD99.60

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
237
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 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 years 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
  • 60 days
From
USD65.00
From
USD65.00

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

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

star-5
299
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
  • 5 hours
  • Free Cancellation
From
USD104.00
From
USD104.00

Chicago Pizza Tour
Likely to Sell OutLikely to Sell Out

Chicago Pizza Tour

star-5
289
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
From
USD75.00
From
USD75.00

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

Chicago Signature Dinner Cruise on Lake Michigan

star-4
181
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
More
  • 3 hours
From
USD122.80
From
USD122.80

River North Food Walking Tour

River North Food Walking Tour

star-4.5
66
Get to know the River North district of Chicago through its food on a culinary walking tour that takes you to five local food venues. You'll enjoy tastings of Mexican fare, Chicago deep dish pizza, and other items while learning about the neighborhood's history and food culture.
More
  • 3 hours
  • Free Cancellation
From
USD75.00
From
USD75.00

African American Heritage Tour of Chicago with Soul Food Meal included

African American Heritage Tour of Chicago with Soul Food Meal included

star-5
13
Immerse yourself in Chicago’s rich and dynamic African American heritage during this private half-day tour. Highlights include interior visits to two African American museums, a stop at the birthplace of gospel music in Bronzeville, and a look at the Obama home in Hyde Park and Kanye West’s lakefront childhood home. A tasty Soul Food buffet is included.
More
  • 4 hours
  • Free Cancellation
From
USD175.00
From
USD175.00

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

star-4.5
24
Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this full-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronzeville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.
More
  • 8 hours 30 minutes
  • Free Cancellation
From
USD175.00
From
USD175.00

Filters

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 by Duration in Chicago?
Q:
What Tours by Duration in Chicago are taking additional safety precautions?
Q:
What Tours by Duration in Chicago are good for avoiding crowds?