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.

Tour Chicago by bus

Enjoy panoramic views of Chicago’s sights and skyscrapers with Big Bus Tours. Their sightseeing tours on double-decker buses cover the city’s top landmarks, from The Magnificent Mile to Millennium Park, with entertaining and educational commentary from a live guide. Plus, all tours are hop-on/hop-off so you can explore the city at your own pace.

If you’re hungry, Pizza City USA offers Chicago pizza bus tours that will whisk visitors around to some of the city’s most unique pizza spots. Highlights include Chicago classics, like deep dish and tavern style, plus bites of Detroit style, New York slices, and Neapolitan pies. A seasoned guide will teach you about local pizza styles and the history behind each slice.

Or tour the city in a luxury vehicle with a guide from Chicago Private Tours, which offers expert tours on Chicago attractions, history, and culture. Customizable to your unique interests, tours are available in English, Spanish, Italian, French, German, Mandarin, and Russian.

See Chicago on bike

Group bike tour
Bike near the zoo in Lincoln Park

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 was voted #1 Tour Company in Chicago by TripAdvisor‘s loyal crowd — not too shabby. And the Bikes at Night 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 580 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.

Chicago Segway tours

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 Absolutely Segway Tours, or City Segway Tours, which both offer a selection of specialty excursions, from a Fireworks Tour that lights up Navy Pier and Buckingham Fountain, to a Riverwalk Tour along the downtown waterfront, to a Holiday Lights Tour during the festive winter months.

Go with #1 Chicago Tours for more Segway excursions — 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!

More ways to see Chicago on wheels

Sightseeing on the l train

Cover more ground with an ‘L’ tour of Chicago. The city’s raised public transit system, known as the ‘L’, is one of the best ways to explore the city. Let L Stop Tours be your guide as you explore different ‘L’ lines and the neighborhoods they connect. Each tour features one to three unique neighborhoods, covering topics like local history, architecture, hidden gems, museums, and more.

Go Chicago
Save up to 55% admissions to Chicago’s top attractions with Go Chicago. Explore Chicago at your own pace. Pay nothing at the gate — just use the pass on your phone or print it out in advance. No need to exchange money or hand over a credit card with contactless scanning at the attraction. The interactive mobile app will have you traveling around the city like a local! Choose from 25+ attractions, including:

  • Skydeck Chicago
  • Shoreline Architecture River Cruise
  • Hop-On Hop-Off Big Bus Tour
  • Art Institute of Chicago
  • Navy Pier rides
  • And so much more!

Explore Go Chicago options:

Go Chicago — All Inclusive
Go Chicago — Explorer
Go Chicago — Build Your Own

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