Recent Searches
Clear

Top Chicago Private and Luxury

Saved to wishlist!
Dates
Select Dates
Architecture Tours
Architecture Tours
City Tours
City Tours
Half-day Tours
Half-day Tours
Historical Tours
Historical Tours
Private Sightseeing Tours
Private Sightseeing Tours
Day Cruises
Day Cruises
Cruises & Sailing
Cruises & Sailing
Night Tours
Night Tours
Crime Tours
Crime Tours
Walking Tours
Walking Tours
Helicopter Tours
Helicopter Tours
Sightseeing Tours
Sightseeing Tours
Classic Car Tours
Classic Car Tours
Food Tours
Food Tours
Photography Tours
Photography Tours
E-Bike Tours
E-Bike Tours
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Ghost & Vampire Tours
Ghost & Vampire Tours
Chocolate Tours
Chocolate Tours
Bus Tours
Bus Tours
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

38 results | All Chicago Tours

Sort by: Featured

Chicago in a Day: Food, History and Architecture Combo Tour
Likely to Sell OutLikely to Sell Out

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

star-5
151
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.
More
  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$104.00
From
$104.00
Taking safety measures

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6841
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).
More
  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
Taking safety measures

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-5
444
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.
More
  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Taking safety measures

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

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

star-5
330
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 Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1292
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
555
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
149
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1093
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$46.00
From
$46.00
Taking safety measures

Chicago CityPASS

Chicago CityPASS

star-4.5
334
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.
More
  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2077
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
284
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$33.00
From
$33.00
Taking safety measures

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

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

star-5
44
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 along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$51.50
From
$51.50
Taking safety measures

2-Hour Chicago Lakefront and Museum Campus Segway Tour

2-Hour Chicago Lakefront and Museum Campus Segway Tour

star-5
173
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.
More
  • 2 hours
From
$73.24
From
$73.24

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
149
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.
More
  • 2 hours
  • Free Cancellation
From
$73.24
From
$73.24

Chicago Hauntings Original Ghost Bus Tour

Chicago Hauntings Original Ghost Bus Tour

star-3.5
101
Calling all fans of the paranormal, this 2.5 to 3-hour ghost bus tour of Chicago takes you into the city’s darkest recesses to reveal its dark past. Travel with ease between locations of reputed haunting and listen to spine-chilling tales delivered by a historian guide. The City Cemetery, the Levee Vice district, and Prairie Avenue all feature on the itinerary, in addition to the site of the notorious St. Valentine’s Day massacre.
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$49.00
From
$49.00
Taking safety measures

Chicago City Minibus Tour

Chicago City Minibus Tour

star-5
54
Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$39.00
From
$39.00
Taking safety measures

Chicago Insider Segway Tour

Chicago Insider Segway Tour

star-5
48
Enjoy an introduction to Chicago’s highlights and history—on wheels. This small-group Segway tour offers a new, and zippy, way to explore. Meet your guide near Millennium Park, and begin with a personalized training session. Once you’re comfortable on your Segway, explore Millennium Park, roll along the Lakefront, and more. As you go, learn little-known Chicago stories and tidbits, from mafia history to the innovations that changed the city.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

star-4
44
Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.
More
  • 1 hour 30 minutes
From
$42.00
From
$42.00

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
39
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$42.67
From
$42.67
Taking safety measures

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
38
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.
More
  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$849.00
per group
From
$849.00
per group
Taking safety measures

2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
27
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.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

2-Hour Chicago Fireworks Segway Tour

2-Hour Chicago Fireworks Segway Tour

star-5
24
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
20
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.
More
  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

star-5
18
Enjoy a private 2-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!
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$200.00
per group
From
$200.00
per group
Taking safety measures

Filters

Frequently Asked Questions