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Top Chicago Tours, Sightseeing & Cruises

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197 Chicago Tours, Sightseeing & Cruises | All Chicago Tours

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Big Bus Chicago Hop-On Hop-Off TourBus Tours

Big Bus Chicago Hop-On Hop-Off Tour

star-4.5
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 live commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$29.00
From
US$29.00
Taking safety measures

Chicago in a Day: Food, History and Architecture Combo TourHalf-day Tours

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

star-5
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
US$102.30
From
US$102.30
Taking safety measures

Chicago Crime and Mob TourBus Tours

Chicago Crime and Mob Tour

star-4
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
US$45.00
From
US$45.00
Taking safety measures

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and MuralsPhotography Tours

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

star-5
Get off the beaten path to experience some of Chicago's best street art on this immersive tour. With a guide in the lead, you can leave the navigation to them and simply take in the scenery. Listen to in-depth commentary focused on the street-art community, the artists, and the history and meaning behind the art.
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  • 2 hours
  • Free Cancellation
From
US$26.67
From
US$26.67

Chicago Grand Half-Day Bus TourHalf-day Tours

Chicago Grand Half-Day Bus Tour

star-3.5
Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$52.95
From
US$52.95
Taking safety measures

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)Attraction Tickets

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

star-3.5
This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$73.95
From
US$73.95
Taking safety measures

Go Chicago Explorer Pass with SkyDeck and 360 ChicagoMulti-day Tours

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
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 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 3, 4, or 5 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 (purchased by December 31) 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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  • 30 days
From
US$66.00
From
US$66.00

Chicago City Minibus Tour with Optional Architecture River CruiseBus Tours

Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
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
US$43.95
From
US$43.95
Taking safety measures

Chicago Night Crimes TourBus Tours

Chicago Night Crimes Tour

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

Gangsters and Ghosts Tour in ChicagoCultural Tours

Gangsters and Ghosts Tour in Chicago

star-4.5
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
US$27.00
From
US$27.00
Taking safety measures

Chicago CityPASSAttraction Tickets

Chicago CityPASS

star-4.5
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, and the Field Museum as well as a choice of the Art Institute of Chicago or Adler Planetarium, and Museum of Science and Industry or 360 Chicago (John Hancock Observatory). Plus enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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  • 9 days
  • Free Cancellation
From
US$109.00
From
US$109.00

360 CHICAGO Observation Deck Admission (Hancock Center)Attraction Tickets

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4.5
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 interactive touch screens and educational exhibits on site. Upgrade to 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
US$22.00
From
US$22.00
Taking safety measures

Chicago North Side TourBus Tours

Chicago North Side Tour

star-4
Explore the North Side of Chicago on this guided sightseeing tour by coach. During this 2-hour tour, experience the bustle of the Loop, the central business district and one of the financial centers of the country. Visit State Street, an important thoroughfare in Chicago's history and the Magnificent Mile along Michigan Avenue. Learn about the history and culture of the city from your local guide; upgrade your tour to include a Chicago River cruise.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$34.95
From
US$34.95
Taking safety measures

Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$28.00
From
US$28.00
Taking safety measures

Chicago History Museum Admission TicketAttraction Tickets

Chicago History Museum Admission Ticket

star-5
See Chicago on more than just a surface level by visiting the Chicago History Museum. Inside, you can delve into the history and culture of Chicago and learn about aspects of the city’s past you might otherwise overlook. A great way to start off your tour of Chicago, the museum provides a foundation for exploring the rest of the city.
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  • 2 to 3 hours
  • Taking safety measures
From
US$19.00
From
US$19.00
Taking safety measures

Underground Donut Tour - Chicago's First Donut TourCulinary & Gourmet Tour

Underground Donut Tour - Chicago's First Donut Tour

star-5
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
From
US$30.00
From
US$30.00

Chicago Style Food TourHalf-day Tours

Chicago Style Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
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  • 3 hours
From
US$71.47
From
US$71.47

Chicago Prohibition Tour Half-day Tours

Chicago Prohibition Tour

star-4.5
Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$55.00
From
US$55.00
Taking safety measures

Famous Tastes of Chicago Food TourHalf-day Tours

Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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  • 3 hours
From
US$68.50
From
US$68.50

Chicago South Side Tour with Optional River CruiseBus Tours

Chicago South Side Tour with Optional River Cruise

star-4
See the landmarks of Chicago’s South Side on a 2-hour coach tour through this historic, diverse and culturally-rich neighborhood. Take in views of Jackson Park and the University of Chicago, pause at the foot of the stunning Lake Point Towers then watch the bustling crowd at Navy Pier. Get a glimpse of American history as you explore President Obama’s former neighborhood and see the President and First Lady’s home; with an optional upgrade, you can finish your trip with a scenic cruise along the Chicago River.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$34.95
From
US$34.95
Taking safety measures

Land and River Architecture Tour of Chicago's Scenic North SideHalf-day Tours

Land and River Architecture Tour of Chicago's Scenic North Side

star-4.5
Discover Chicago’s iconic architectural gems from every angle on a 3.5-hour tour of the North Side. Divided between land and water, the comprehensive tour enables you to cover a huge area of the city without getting worn out. Travel comfortably by coach or trolley to Fort Dearborn, Wrigley Building, and more. Afterwards, see the Windy City's famous skyscrapers, bridges, and historical sites on a 90-minute cruise down Chicago River.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$76.95
From
US$76.95
Taking safety measures

Chicago Favorites Ultimate Food & Walking TourBeer & Brewery Tours

Chicago Favorites Ultimate Food & Walking Tour

star-5
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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  • 2 hours 30 minutes
  • Taking safety measures
From
US$62.99
From
US$62.99
Taking safety measures

Chicago Architecture River CruiseDay Cruises

SPECIAL OFFER

Chicago Architecture River Cruise

star-5
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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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$35.49
US$40.33
US$4.84 savings
From
US$35.49
US$40.33
US$4.84 savings
Taking safety measures

Chicago Loop Secret Food Tour w/ Private Tour OptionHalf-day Tours

Chicago Loop Secret Food Tour w/ Private Tour Option

star-5
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
US$81.48
From
US$81.48
Taking safety measures

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