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39 Chicago Private and Luxury | All Chicago Tours

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

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

star-5
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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  • 4 hours
  • Taking safety measures
From
$79.99
From
$79.99
Taking safety measures

2-Hour Chicago Lakefront and Museum Campus Segway Tour

2-Hour Chicago Lakefront and Museum Campus Segway Tour

star-5
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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  • 2 hours
From
$73.24
From
$73.24

Chicago Lakefront and Museum Campus Small-Group Segway Tour

Chicago Lakefront and Museum Campus Small-Group Segway Tour

star-5
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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  • 2 hours 30 minutes
  • Free Cancellation
From
$79.06
From
$79.06

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
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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  • 2 hours
  • Free Cancellation
From
$30.00
From
$30.00

Chicago Prohibition Tour

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
$55.00
From
$55.00
Taking safety measures

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
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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  • 2 hours
  • Free Cancellation
From
$40.00
From
$40.00

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

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
$102.30
From
$102.30
Taking safety measures

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

star-5
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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  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$622.20
per group
From
$622.20
per group
Taking safety measures

2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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  • 2 hours
  • Free Cancellation
From
$75.00
From
$75.00

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.63
From
$50.63
Taking safety measures

Lonely Planet Experiences: River North Historical Food Tour

Lonely Planet Experiences: River North Historical Food Tour

star-5
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$60.96
From
$60.96
Taking safety measures

Millennium Park Photo Shoot and Walking Tour

Millennium Park Photo Shoot and Walking Tour

star-5
On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.
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  • 1 to 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Private Chicago Architecture Tour

Private Chicago Architecture Tour

star-5
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$660.00
per group
From
$660.00
per group
Taking safety measures

Chicago City Minibus Tour with Optional Architecture River Cruise

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
$43.95
From
$43.95
Taking safety measures

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$660.00
per group
From
$660.00
per group
Taking safety measures

Navy Pier Photo Shoot and Walking Tour

Navy Pier Photo Shoot and Walking Tour

star-5
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: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours
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  • 1 to 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Cultural Mile Walking Tour of Chicago

Cultural Mile Walking Tour of Chicago

star-5
Discover the sights and sounds of Chicago’s various cultural scenes on a 2-hour walking tour. The 1.5-mile route covers music, literature, art, and architecture within the Windy City. Hear insider stories about Chicago's cultural movements and visit little-known locations linked to iconic artists.  Be sure to have your camera ready for the pièce de résistance, the Tiffany stained glass dome at the Chicago Cultural Center.
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  • 2 hours
  • Free Cancellation
From
$40.00
From
$40.00

2-Hour Chicago Holiday Lights Segway Tour

2-Hour Chicago Holiday Lights Segway Tour

star-4.5
Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive department store displays. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.
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  • 2 hours to 2 hours 15 minutes
  • Free Cancellation
From
$75.10
From
$75.10

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10

Chicago Insider Segway Tour in Small Group

Chicago Insider Segway Tour in Small Group

star-5
This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

2-Hour Chicago City Lights and Skyline Segway Tour

2-Hour Chicago City Lights and Skyline Segway Tour

star-4
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field and Michigan Avenue. 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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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)

Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)

star-5
Enjoy a private 4-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French or Dutch. Focus can be on public or street art, architecture, food and much more!
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$320.00
per group
From
$320.00
per group
Taking safety measures

Lincoln Park Photo Shoot and Walking Tour

Lincoln Park Photo Shoot and Walking Tour

star-5
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.
More
  • 1 to 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Chicago Haunted Halloween Segway Tour

Chicago Haunted Halloween Segway Tour

star-4.5
Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your local guide, and see alleys, hotels and sites of some of the most gruesome disasters and murders in Chicago’s history. During your spooky adventure through the city, you’ll also see Chicago's famous landmarks lit up in glistening lights. Join in the Halloween fun all October long! Costumed guides and ghoulish tales--this haunting good-time is not to be missed!
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  • 2 hours
From
$75.58
From
$75.58

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