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Top Chicago Classic Car Tours

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12 results | All Chicago Tours

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8527
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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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

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

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

star-4.5
143
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
USD40.00
From
USD40.00

360 CHICAGO Observation Deck Admission (Hancock Center)
Likely to Sell OutLikely to Sell Out

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
330
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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  • 1 to 4 hours
  • Free Cancellation
From
USD30.00
From
USD30.00

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
475
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.
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  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

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.
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  • 4 hours
  • Free Cancellation
From
USD700.00
per group
From
USD700.00
per group

Chicago CityPASS

Chicago CityPASS

star-4.5
367
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, 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. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
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  • 9 days
  • Free Cancellation
From
USD114.00
From
USD114.00

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
174
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
  • Free Cancellation
From
USD76.48
From
USD76.48

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2907
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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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2205
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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  • 1 hour 30 minutes
  • Free Cancellation
From
USD42.00
From
USD42.00

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.
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  • 1 hour
  • Free Cancellation
From
USD18.00
From
USD18.00

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
237
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.
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  • 60 days
From
USD65.00
From
USD65.00

2-Hour Chicago Fireworks Segway Tour

2-Hour Chicago Fireworks Segway Tour

star-5
26
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.
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  • 2 hours
  • Free Cancellation
From
USD78.43
From
USD78.43

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What people are saying about Classic Car Tours in Chicago

star-5
Chicago Architecture River Cruise
"Spiro made the trip very interesting. I don't think the cruise would have been as good if it were not for Spiro."..."
star-5
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
"Went on a couples date but will be going back with the kids. Very fun. Can’t wait to go back again.!"..."
star-5
360 CHICAGO Observation Deck Admission (Hancock Center)
"Long lines but they move pretty quickly. The view is absolutely breathtaking once you make it to the top. ❤️"..."
star-5
Chicago Favorites Ultimate Food & Walking Tour
"The food was delicious ! I loved getting to know the history of the city! Tour guide was very friendly"..."
star-5
Chicago CityPASS
"family memories- great weather- but around Wrigley park dirty part of city - people are somewhat nice - got some very rude people in Chicago"..."
star-5
Chicago Lakefront and Museum Campus Small Group Tour
"Tammy was a wonderful guide! I was nervous because I had never done anything like this before but she was patient and helpful and we all caught on quickly! We had a blast and have already signed up to do another one on our next vacation! Thank you Tammy!!"..."
star-5
Gangsters and Ghosts Tour in Chicago
"Stories of the tragedies that shaped Chicago and the countries ruled and laws. Would recommend this to everyone"..."
star-5
90-Minute Chicago River Architecture Tour
"Really enjoyed the view and the knowledge of our tour guide. Would highly recommend going on this tour."..."
star-5
Behind-the-Scenes Tour of Historic Chicago Theatre
"Tour guide was excellent and the Theatre is just amazing. From the history to the breathtaking details of its structure, it is a must see on your trip to Chicago!"..."
star-5
Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions
"We used the Explorer Pass for our first day in Chicago for the Hop on Hop off bus and the Architectural river cruise. It was fantastic. We just showed our tickets at each location and were able to exchange for tickets. We still have another activity for tomorrow on our 3 activity pass. Well worth the price and convenience."..."
star-5
2-Hour Chicago Fireworks Segway Tour
"Excellent training & lots of Chicago history: the beautiful Chicago skyline & fireworks made it spectacular!"..."
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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?
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What Classic Car Tours in Chicago are taking additional safety precautions?
Q:
What Classic Car Tours in Chicago are good for avoiding crowds?