Top Chicago Segway Tours

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Lakefront Segway Tour in Chicago

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Chicago Landmarks and Museum Campus Small Group Segway Tour

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.

Chicago Insider Segway Tour

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90 Minute Architecture Tour

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

1 hour to 1 hour 15 minutesFree Cancellation

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,328)

from $27

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

Enjoy a new perspective on the Windy City—and see more of its sights in less time, all without breaking a sweat—on this small-group, sunset Segway tour. With included instruction and hands-on guidance, get comfortable on your Segway in no time. Then, set off to discover top Chicago highlights from the Museum Campus and Millennium Park to Buckingham Fountain and beyond, all while the city's lights slowly come on.

Chicago Sunset Segway Tour

Haunted Ghosts & The Chicago Outfit Segway Tour

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

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.

Chicago City Minibus Tour

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

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 Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

Must-Dos in Chicago

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What are people saying about Chicago

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Cheryl_D, Oct 2026

Segway Fun in Chicago

The Segway tour with Mike was one of the highlights of our time in Chicago! He was attentive, knowledgeable, and made sure everyone felt comfortable and included throughout the tour. We learned so much while seeing the city in a fun, memorable way. If you’re visiting Chicago, this tour with Mike is a must-do!

Field Museum of Natural History Admission Tickets

Kathleen_H, Oct 2026

Don’t miss it, whoever you are.

It might be good to talk about what you want to do when you first get there. I recommend SUE. Older kids can figure it all out from there and it’s all spectacular. My advice to parents of younger children: have a plan tailored to them, like seeing the animals. Their attention spans are usually pretty short and they won’t necessarily be interested in the things you and your older children will want to dive into. HAVE FUN!!!

Private 45-Minute Chicago Skyline Helicopter Tour

Jayme_K, Jul 2026

Great View

What an incredible experience! The helicopter ride gave us breathtaking views of the Chicago skyline, Lake Michigan, and all the iconic landmarks. The staff was friendly, professional, and made us feel safe from start to finish. It was smooth, exciting, and definitely one of the highlights of our trip. Highly recommend to anyone looking for a unique way to see Chicago!

Lakefront Segway Tour in Chicago

CALEB_H, Jun 2026

Party Marty For the Win!

Party Marty was my tour guide. He is a born and raised local and gave me such an intimate trip. I left feeling like I got to see a good bit of the city and unearthed local lore I wouldn’t have found through anyone else. By the end of it our day felt more like riding bikes with a friend than a tour. Thanks again Marty.

Chicago Sunset Segway Tour

Mark_N, Jun 2026

10 out of 10

10 out of 10. Would recommend. Every time you go to a Chicago. The Segways are sooooo fun to ride. My 13 year old daughter was very cautious at first but mastered it quickly. My 17 year took to it immediately. Party Marty, our tour guide was excellent. He was funny, charismatic, and very knowledgeable about the area. He also takes incredible pictures and videos. The tour takes you through multiple downtown waterfront parks, and the views of the skyline are incredible.