Top Chicago Segway Tours

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.

5.0

(349)

from $70

2-Hour Guided Segway Tour of 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.

(496)

from $65

Chicago Landmarks & Museum Campus Small Group 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.

5.0

(230)

from $70

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

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.

(3,171)

from $28

Chicago River 90-Minute Architecture Tour

Lakefront Segway Tour in Chicago

(9,950)

from $45

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.

4.6

(145)

from $70

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,039)

from $39

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

4.8

(26)

from $75

Likely to Sell Out

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.

(38)

from $75

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,239)

from $30

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

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Lake Michigan 30-Minute Speedboat Ride

30 minutesFree Cancellation

4.1

(337)

from $36

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

4.8

(128)

from $849

Per group

Likely to Sell Out

Chicago Lake and River Architecture 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).

(2,330)

from $45

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(909)

from $33

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

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.

(566)

from $50

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

3 hoursFree Cancellation

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.

(243)

from $59

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(515)

from $29

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

2 hours 20 minutesFree Cancellation

Experience Chicago at its most magical—and admire views that few other visitors get to see—on this evening Segway tour. Visit popular Grant Park and see Buckingham Fountain’s summertime light show, with an illuminated Windy City skyline as the perfect backdrop. Then, glide along the lakefront, and admire Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included.

(52)

from $72

Chicago Pier Fireworks Segway Tour

2-Hour Chicago Lakefront & Museum Campus Segway Tour

(34)

from $80

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Reimay_N, Apr 2026

Super fun! Try it, you won’t regret it!

If you don’t like standing around and reading plaques in museums all day, or you can’t find parking and are walking around Chicago’s parks but that’s too slow for you, or if you’re a human, you’ll like this! It’s fun from the hands-on aspect and the novelty of gliding on a Segway. Totally worth it, Chicago has a large and beautiful outdoor expanse that’s just perfect for Segwaying along. Marshall was our guide, he was super knowledgeable and shared many interesting details about Chicago! Only recommendation other than to DO IT!! is get there early if you’re a tourist. It’s a lot harder to find than we thought. The tour ends at the same time regardless of when you get there, so if you arrive early for training you’ll get the most time on a Segway in the parks.

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

2-Hour Guided Segway Tour of Chicago

Jeffrey_P, Nov 2025

A fun time

My daughter and I really enjoyed this experience. We had no previous experience driving a Segway but the instructions given were great and we were riding along in no time. The tour itself was informative and funny. We really enjoyed this and look forward to doing it again the next time we come to Chicago

Chicago Landmarks & Museum Campus Small Group Segway Tour

Jennifer_P, Jul 2025

Chitown’s Abundant Wonders!

The experience was well worth the ticket price. You safety travel to see many interesting and picturesque sights. I loved seeing everyone by Segway. The guide was very knowledgeable and gave the experience that extra Chitown’s flavor. It was Supa Dupa!!!!

Bike Tour of Chicago's Lakefront Neighborhoods

Veronica_P, Jun 2025

Fabulous up close tour of a beautiful and interesting city. Will be back.

Wonderful, informative and inspirational biking experience. Enjoyed seeing details of the city that you would miss driving by. Be prepared to ride and stop for a few hours and 9-10 miles. In very hot weather, it can be uncomfortable at times. Liam was our guide and he paced us well. Very much enjoyed.

Chicago Pier Fireworks Segway Tour

Tennille_J, Jun 2025

Amazing evening tour!

My 15 yr old son & I tried this for the first time & it was so much fun! Our guide Kevin, was good at instruction of the Segways to make sure we felt comfortable riding them, & explaining all the attractions downtown. We got to see so many things we never even knew existed in Chicago. I highly recommend doing the evening tour with the fireworks over Navy Pier- our view of the skyline was absolutely amazing! We would definitely do this again!

Lakefront Segway Tour in Chicago

Braden_B, Jun 2025

5 Stars – Fun, Safe, and Scenic Segway Tour of Chicago!

We had an amazing time on this Segway tour of Chicago’s lakefront! It was a beautiful day, and cruising on a Segway made it even better. Our guide, Joe, was awesome - super friendly, knowledgeable, and fun. He kept the group engaged and made sure everyone felt comfortable the whole time. We visited iconic spots like Buckingham Fountain, Soldier Field, and Grant Park, all while learning obscure interesting facts about the city. The Segways were easy to maneuver, and we never felt unsafe. Joe gave great instructions and kept an eye on everyone. This was such a fun and informative way to see the city. Highly recommend if you’re looking for something unique and enjoyable to do in Chicago!