Recent Searches
Clear

Top Chicago Classic Car Tours

Saved to wishlist!
Dates
Select Dates
Private and Luxury
Private and Luxury
City Tours
City Tours
Bus Tours
Bus Tours
Car Tours
Car Tours
Private Sightseeing Tours
Private Sightseeing Tours
Half-day Tours
Half-day Tours
Sightseeing Tours
Sightseeing Tours
Water Tours
Water Tours
Arts & Design
Arts & Design
Walking Tours
Walking Tours
Museums
Museums
Kid-Friendly
Segway Tours
Segway Tours
Historical Tours
Historical Tours
Sightseeing Passes
Sightseeing Passes
Day Cruises
Day Cruises
Museum Tickets & Passes
Museum Tickets & Passes
Unique Experiences
Unique Experiences
Sightseeing Cruises
Sightseeing Cruises
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

12 results | All Chicago Tours

Sort by: Featured

Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7010
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
  • Free Cancellation
From
$40.33
From
$40.33

Chicago Spray Paint 'n' Sip at Studio W.I.P.- BYOB

Chicago Spray Paint 'n' Sip at Studio W.I.P.- BYOB

star-5
74
Enjoy a unique creative outlet—and learn the ins and outs of graffiti and street art—during this hands-on urban art workshop. Pick from multiple class times, and make your own way to the Chicago studio. You’ll learn different styles and techniques from your instructors (including guest artists), can try out stenciling and spray-painting, and can even create your own work of art on canvas to bring home at the end of class.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
297
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. Upgrade your tour to include three pours of local craft beer.
More
  • 3 hours
  • Free Cancellation
From
$69.99
From
$69.99

4-Hour Chicago City Tour by SUV

4-Hour Chicago City Tour by SUV

Have only a limited amount of time to explore the Windy City? Leave the planning to someone else with this convenient SUV transfer service. Meet your private driver at a time and place that work best for you, and set off: You’ll be dropped off directly at top Chicago landmarks like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park, with time for solo sightseeing at each stop.
More
  • 4 hours
  • Free Cancellation
From
$540.00
per group
From
$540.00
per group

Chicago CityPASS

Chicago CityPASS

star-4.5
335
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

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
150
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

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2191
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
From
$35.00
From
$35.00

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1363
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
From
$40.00
From
$40.00

Behind-the-Scenes Tour of Historic Chicago Theatre

Behind-the-Scenes Tour of Historic Chicago Theatre

star-4.5
21
Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
More
  • 1 hour
  • Free Cancellation
From
$18.00
From
$18.00

Field Museum of Natural History All-Access Pass

Field Museum of Natural History All-Access Pass

star-4.5
63
One of Chicago’s most popular and recognizable landmarks, the Field Museum of Natural History offers a wide array of treasures, from its Hall of Gems to Sue—one of the best-preserved Tyrannosaurus Rex fossils ever found. Guarantee your admission to this in-demand museum, and prevent any stress, by booking your tickets before you travel. Upon arrival, you can explore the museum at your own pace, and even embark on a complimentary, docent-led tour.
More
  • 1 to 8 hours
  • Free Cancellation
From
$40.00
From
$40.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
218
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 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 years 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.
More
  • 60 days
From
$59.00
From
$59.00

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

Filters

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Classic Car Tours in Chicago?
Q:
What Classic Car Tours in Chicago are taking additional safety precautions?
Q:
What Classic Car Tours in Chicago are good for avoiding crowds?