You can see Chicago from any angle: from high above in the sky, along the shores on a boat and on the ground with your own two feet. So it stands to reason that you can also explore the city on wheels. Take your pick of vehicle – bus, bike, Segway or Trikke – with these Chicago tours.

Four-wheeled fun

You'll recognize the big, bright red buses from Chicago Trolley & Double Decker Company throughout the city. Check out the famous Hop On, Hop Off Tour that covers miles of city attractions and offers you the opportunity to jump off the bus for a close-up look and jump back on when you're ready to roll on to the next stop for more sightseeing. Even better, you can keep the ride inside or outside on the Double Decker tour, with enclosed seating on the lower level and open air seating – and views – up top. Adding to the entertainment factor, the guides are always good for a laugh.

Or tour the city in a luxury vehicle with a guide from Chicago Private Tours, who's an expert on Chicago attractions, history and culture. Customizable to meet your particular interests, tours are available in English, Spanish, Italian, French, Greek, German, Mandarin, Russian and Japanese among the many other languages.

Trek across town on two wheels

Combine your love for exploration with a little exercise on a bike tour. Chicago's smooth, flat terrain makes it easy to sightsee by bicycle, with tour possibilities covering everything from neighborhood outings to food adventures. Bobby's Bike Hike and their Lakefront Neighborhoods Tour was recently voted Best Tour in Chicago by TripAdvisor's loyal crowd – not too shabby. And the Bikes @ Nite Tour with Bike and Roll shows off Chicago's sparkly side when the sun goes down and the downtown lights come on.

Join the local cyclists who cruise the bike lanes using the city's bike sharing system, Divvy. Painted a bright baby blue, you'll spot this fleet right away. Bike share racks are parked at major hubs across town (there are over 300 stations) and a 24-hour pass can be purchased on-site anytime, making for a convenient way to have access to your own wheels just about anywhere.

Don't want to break a sweat? Rev up your urban spirit and experience the city with ease on an electric bike with WanderBikes, the only dedicated electric bike rental and guided tour operation in Chicago. Whether you decide to roam on your own, or join them for a tour, sightseeing has never been easier. Cruising at a comfortable 15 mph, you'll see and do more in less time with WanderBikes.

Think outside the norm with these rides

But a bike isn't the only way to cruise around Chicago on two wheels. If you don't feel like pedaling, zoom around with the skyline in view on a futuristic Segway. Step onto your two-wheeled self-balancing ride and cruise down Chicago's streets. Try Segway Experience of ChicagoAbsolutely Segway Tours, or City Segway Tours, which all offer a selection of specialty excursions, from a Fireworks Tour that lights up Navy Pier and Buckingham Fountain, to a Riverwalk Tour that passes under Trump Tower, to a Holiday Lights Tour during the festive winter months.

Go with #1 Chicago Tours for more segway excursions – try Steve's Segway North Tour and Steve's Segway Museum Campus Tour – or take it one wheel further with a three-wheeled Trikke. Lean into the wind on these stable, user-friendly electric rides while you learn about top sights like the gorgeous open parks and scenic lakefront on their Trikke Chicago Tour.

No matter your age or fitness level, there's a tour for you. Grab some wheels and go!


Please note: Some of the above tours are available seasonally and are weather dependent. Please check with each tour company for availability.


Related Listings

#1 Chicago Tours
155 N. Harbor Dr.
Chicago, IL 60601
(312) 946-9467

658 N. Milwaukee Ave.
Chicago, IL 60647
(855) 553-4889

City Segway Tours - Chicago
910 S. Michigan Ave.
Chicago, IL 60605
(312) 819-0186

Absolutely Chicago Segway Tours
238 E. Monroe
Chicago, IL 60603
(312) 552-5100

Bobby’s Bike Hike Chicago – Bike, Walking, Food Tours & Rentals
540 N. Lake Shore Dr.
Chicago, IL 60611
(312) 245-9300

Chicago Trolley and Double Decker Co.
Water Tower Pumping Station
Chicago, IL 60611
(773) 648-5000

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