Top Chicago Sightseeing Tours
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109 results | All Chicago Tours
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Big Bus Chicago Hop-On Hop-Off Tour
701
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
Learn More

Go Chicago Explorer Pass with SkyDeck and 360 Chicago
199
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 City Minibus Tour with Optional Architecture River Cruise
357
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
$39.00
From
$39.00
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

Chicago Night Crimes Bus Tour
51
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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From
$50.00
From
$50.00
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

Chicago CityPASS
302
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 (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck.
Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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From
$109.00
From
$109.00

Go Chicago All-Inclusive Pass with Skip the Line Access
23
Enjoy admission to more than 25 of Chicago's most popular attractions with the Go Chicago™ All-Inclusive Pass. Create your own itinerary and sightsee at your own pace.Take a hop-on hop-off bus tour of the Windy City, check out the fascinating exhibits at Shedd Aquarium, admire the stunning views from SkyDeck Chicago, and much more. Save your pass, available as your 'ticket' after purchase, on your mobile device; don't waste time redeeming vouchers. This pass offers something for all members of the family. The Go Chicago™ All-Inclusive Pass is available in 1-, 2-, 3-, or 5-day options.
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 the number of remaining consecutive days purchased.
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From
$114.00
From
$114.00

Chicago Lakefront and Museum Campus Small-Group Segway Tour
132
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

Big Bus Chicago Night Tour
39
See Chicago's dazzling skyscrapers lit up for the night during this 75-minute Big Bus tour. The entire loop takes passengers from the Magnificent Mile to Michigan Avenue, through the Museum Campus and around the architectural gems on the Loop skyline. Live commentary in English.
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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
Learn More

Private Chicago City Tour
130
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

2-Hour Chicago Lakefront and Museum Campus Segway Tour
79
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.
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From
$73.24
From
$73.24

Chicago Lake and River Architecture Tour
213
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.
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From
$39.00
From
$39.00
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

Chicago Architecture River Cruise
4770
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). From Memorial Day to Labor Day (May 29 - September 6,) each ticket includes a one-way water taxi ticket.
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From
$38.15
From
$38.15
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More

360 CHICAGO Observation Deck Admission (Hancock Center)
252
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.
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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
Hand sanitizer available to travelers and staff
Learn More

We Love Chicago Walking Tour
10
Downtown Chicago is filled with gems. Some famous, others known only by select locals. Many of these spots are best seen on foot as opposed to a moving vehicle. We'll take you inside several of these architectural masterpieces, to where much of Chicago's real beauty can be seen. We'll also give you time to check out famous public art by the likes of Picasso and Chagall and see the world's very first skyscrapers! All of our tours are led by experienced guide that have been giving quality tours of Chicago since 2005 and have accrued well over 500 five-star reviews. People mostly comment on how our tours are both informative and entertaining. The walk is a little under 2 miles and conducted at a comfortable pace.
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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
Hand sanitizer available to travelers and staff
Learn More

90-Minute Chicago River Architecture Tour
499
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.
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From
$39.00
From
$39.00
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

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
217
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
Learn More

Sparkling Chicago: 360 CHICAGO Observation Deck (Hancock Center) with Prosecco
13
This admission ticket for two people gets you and a special someone access to 360 Chicago (John Hancock Observatory) plus a half bottle of Prosecco — a package that’s not available for purchase at the tower. After a quick elevator ride to the 94th floor of the Hancock Center, savor panoramic views over Chicago from 1,000 feet (304 meters) above the Magnificent Mile. Lift your glass in a toast to landmarks like Navy Pier, the Willis (Sears) Tower and Lake Michigan. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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From
$70.00
From
$70.00
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

Chicago Riverwalk Photo Shoot and Walking Tour
1
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir.
Your photo tour includes:
-Your choice of a 30 minute or 1-hour private tour with a professional photographer
-High-resolution edited images delivered via a private online gallery within 1-2 days
-Enjoy unlimited access to your photos and download as many as you would like with no expiration date
*not all stops may be included depending on the length of time you select.
…More
From
$150.00
per group
From
$150.00
per group
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Learn More

Chicago Family Food & Bike Tour with Top Attractions
35
See Chicago light up with a 4-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 daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, Italian beef, and a tasty dessert for good measure. Upgrade your experience to enjoy a locally crafted beer pairing at three of the food stops. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
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From
$79.99
From
$79.99
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

2-Hour Guided Segway Tour of Chicago
65
2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!
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From
$65.00
From
$65.00

Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk
3
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood.
The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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From
$5.34
From
$5.34

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)
75
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
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Private Al Capone Gangster Tour in Chicago
2
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
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From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
Learn More

Bike Tour of Chicago's Lakefront Neighborhoods
129
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
Learn More
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