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Top Chicago Half-day Tours

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Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

See Chicago from several angles, including the 103rd floor of Willis (Sears) Tower, where you have early access to the Skydeck. This Viator VIP package — available nowhere else — provides a crowd-free morning overlooking city landmarks from glass-enclosed balconies. Follow up your vista with a 2-hour narrated trolley tour past Grant Park, the John Hancock Center, the Wrigley Building and more. Finish with an afternoon cruise on the Chicago River and enjoy a complimentary drink as you discover the city's distinctive skyscrapers from an architecture-savvy guide.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
US$124.00
From  
US$124.00
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Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this 4-hour bike tour through the windy city. You’ll 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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$77.99
From  
US$77.99
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Chicago Prohibition Tour

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.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$45.00
From  
US$45.00
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Chicago Grand Half-Day Tour

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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$49.95
From  
US$49.95
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Chicago Segway Tour

Glide around Chicago and along Lake Shore Drive past Lake Michigan on your very own Segway. After a 30-minute orientation session, you’re off to see highlights of the Windy City with an expert guide. View city sights such as Navy Pier, Buckingham Fountain, Museum Campus, Millennium Park, Grant Park and more. Select a 2- or 3-hour tour in the morning or afternoon. Numbers are limited to eight passengers per guide for a personalized experience.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$70.85
From  
US$70.85
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Chicago Land and River Architecture Tour: North and South Shores

Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$89.95
From  
US$89.95
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Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

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.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$65.00
From  
US$65.00
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Frank Lloyd Wright by Bus Tour from Chicago

Take a deep dive in to Frank Lloyd Wright's Prairie Style on this 4-hour architecture tour of Oak Park from Chicago. Listen to your guide's commentary during the trip, then take a walking tour of the Frank Lloyd Wright Historic District and a tour of the architect's home and studio.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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Famous Tastes of Chicago Food Tour

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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$63.50
From  
US$63.50
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Chicago's Chinatown Food and Walking Tour

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. You'll enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$59.99
From  
US$59.99
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Holiday Hike: Festive Chicago Food and Walking Tour

Stroll through Chicago's winter streets, lit up for the holidays, on this 3-hour walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows at Macy's, and ice skating at Millennium Park. Follow your local guide on a walk down festively decorated State Street and sample generous tastes of classic Chicago foods and holiday treats. Seasonal craft beer tastings will help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$80.00
From  
US$80.00
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Best of Chicago Tour Including a Deep-Dish Pizza

Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
  • Duration: 5 hours 30 minutes
  • Free Cancellation
  • Duration: 5 hours 30 minutes
  • Free Cancellation
From  
US$71.95
From  
US$71.95
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Chicago Lincoln Park Bike Adventure

Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$42.50
From  
US$42.50
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Chicago Style Food Tour

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 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.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$63.50
From  
US$63.50
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Small-Group Chicago Food Tour: Chinatown

Sample different styles and varieties of Chinese food during this 3-hour walking tour of Chicago's Chinatown. Follow your local food-loving guide through one of the oldest Chinese neighborhoods in the country to taste Mandarin-style, Hong Kong-style and Szechuan-style delicacies. The price of this small-group tour, limited to 12 people, includes tastings at 5 restaurants; enough food to add up to a full lunch.
  • Duration: 3 hours 25 minutes
  • Free Cancellation
  • Duration: 3 hours 25 minutes
  • Free Cancellation
From  
US$60.00
From  
US$60.00
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Chicago Architectural Aficionados Bus Tour

Get an overview of Chicago's famous architectural history on this 3.5-hour bus tour. Learn about the city's history through your guide's history, from its founding to the present. Stops include the Loop, Mies van der Rohe's IIT campus, Frank Lloyd Wright's Robie House, and the Museum Campus.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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Chicago Lakefront Neighborhoods Bicycle Tour

Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour 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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$53.99
From  
US$53.99
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Private Chicago Craft Beer and Pizza Tour

Visit three of Chicago’s top craft breweries on a customizable 4-hour tour. Bring your own group of 4 to 11 people on this all-inclusive tour led by a private guide, who shares details about Chicago’s craft brewing scene. Choose the breweries you wish to visit, and pair those suds with an included pizza dinner as well. You’ll learn how these hand-crafted beers are produced, and tour one of the brewery facilities (if available). No need to worry about getting from place to place: Transportation and hotel pickup and drop-off has included, so all you'll have to worry about is which beer to try first.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$129.00
From  
US$129.00
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SPECIAL OFFER

Chicago's Electric Bikes at Night Tour

See Chicago light up at night with a 3-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in evening views of Millennium Park and the Museum Campus. Pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
US$64.75
US$8.76 savings
From  
US$55.99
US$64.75US$8.76 savings
US$64.75
US$8.76 savings
From  
US$55.99
US$64.75US$8.76 savingsSee Details

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Taste food from around the world on this 4-hour cycling tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Mexican tortas, French sweets, and Polish pierogis.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$77.99
From  
US$77.99
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Private Chicago Highlights Driving Tour

Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$99.00
From  
US$99.00
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The Original 1893 Chicago World's Fair Food Tour

Travel back in time to the original 1893 World’s Fair in Chicago for this guided, 3.5-hour food tour. Led by Chicago’s ‘Gold Coast Queen,’ Bertha Palmer, hear her favorite memories from the great 1893 Columbian Exposition and enjoy five different food tastings from around the Windy City.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$78.00
From  
US$78.00
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Scenic Chicago North Side Tour and 360 CHICAGO Observation Deck

Discover the sights of North Chicago on a 2-hour group walking tour. Offered in the morning and afternoon, select a start time that fits with your schedule. Follow your guide to Millennium Park, Lake Michigan, and more. Feel free to pause for photos and ask questions whenever you like. You also get free admission to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$51.95
From  
US$51.95
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Chicago History and Architecture Tour

Learn about Chicago's history and architecture and discover the Loop (Chicago's central business district) on this guided, 3-hour walking tour. You'll visit the Pedway, a system of underground tunnels and overhead bridges in the heart of the Windy City that connects over 40 blocks, covering approximately five miles. Learn to navigate these winding passages and hear interesting stories about Chicago’s past, present and future along the way. Also, stroll across the Michigan Avenue Bridge to the newly expanded Chicago Riverwalk and beyond.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$25.00
From  
US$25.00
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(888) 651-9785
(888) 651-9785