Top Chicago City Tours
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101 results | All Chicago Tours
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Chicago Architecture River Cruise
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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From
$38.85
From
$38.85
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience

Gangsters and Ghosts Tour in Chicago
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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From
$27.00
From
$27.00
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
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.
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From
$84.99
From
$84.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Underground Donut Tour: Chicago's First Donut Tour
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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From
$30.00
From
$30.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers

Chicago Loop Secret Food Tour w/ Private Tour Option
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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From
$193.20
From
$193.20
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Grand Half-Day Bus 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.
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From
$52.95
From
$52.95
Transportation vehicles regularly sanitized

Big Bus Chicago Hop-On Hop-Off Tour
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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From
$26.10
From
$26.10
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers

Chicago in a Day: Food, History and Architecture Combo Tour
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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From
$102.30
From
$102.30
Social distancing enforced throughout experience
Guides required to regularly wash hands
Paid stay-at-home policy for staff with symptoms

Go Chicago Explorer Pass with SkyDeck and 360 Chicago
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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From
$66.00
From
$66.00

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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From
$30.00
From
$30.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers

Chicago Lakefront and Museum Campus Small-Group Segway Tour
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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From
$79.06
From
$79.06

Chicago City Minibus Tour with Optional Architecture River Cruise
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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From
$39.95
From
$39.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago's Ultimate City Bike Tour
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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From
$49.99
From
$49.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Favorites Ultimate Food & Walking Tour
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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From
$62.99
From
$62.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Lake Michigan Sightseeing Cruise
Take in superlative-worthy 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 iconic 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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From
$25.07
From
$25.07
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience

Small-Group Chicago Food Tour: Gold Coast and Old Town
Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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From
$74.67
From
$74.67

Bike Tour of Chicago's Lakefront Neighborhoods
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.
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From
$49.99
From
$49.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Gateway to Chicago's West Loop Food Tour
Get a taste of the deliciousness that finds a home in the Loop of Chicago. Lots of creative eateries ply their wares in the West Loop, and this guided tour helps you find some of the best. You will sample dishes at each stop with a bit of walking through the bustling neighborhood between each.
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From
$85.34
From
$85.34

Private Chicago City Tour
Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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From
$425.34
per group
From
$425.34
per group

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.
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From
$73.95
From
$73.95
Transportation vehicles regularly sanitized

Signature Food Tour at Chicago's Navy Pier
Chicago is full of unique and delicious food, but you don’t need to waste time chasing down each dish individually throughout the city. This food tour of Navy Pier will conveniently introduce you to some of the most authentic Chicago cuisine, all in one handy location. Get insider tips from your ‘food ambassador’ tour guide, who will make sure you end the tour full of delicious food and new knowledge.
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From
$64.00
From
$64.00

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)
Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
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From
$622.20
per group
From
$622.20
per group
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Transportation vehicles regularly sanitized

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
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From
$84.99
From
$84.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff

Chicago Loop Walking Tour
Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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From
$40.00
From
$40.00
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- Lookingglass Theatre Company
- Northerly Island
- Chicago Lakefront Trail
- Chicago Cultural Center
- Prairie Avenue Historic District
- Harold Washington Library Center (Chicago Public Library)
- Marina City
- Marquette Building
- Jackson Park
- Wrigleyville
- Medieval Times Chicago
- Chicago Temple
- Chicago Theatre
- Lincoln Monument
- Chicago Riverwalk
- American Writers Museum
- University of Chicago
- Lincoln Park Conservatory
- House of Blues
- Grant Park
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