Top Chicago Segway Tours

2-Hour Chicago Lakefront & Museum Campus 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.

Special Offer

Chicago Insider Segway Tour

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.

Special Offer

Chicago Pier Fireworks Segway Tour

Lakefront Segway Tour in Chicago

Special Offer

1 hour 30 minutesFree Cancellation

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

5.0

(237)

from $70

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.

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

(3,547)

from $28

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.

Explore Chicago's legendary architecture and history.

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

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.

(10,852)

from $45

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,901)

from $39

Haunted Ghosts & The Chicago Outfit Segway Tour

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.

(38)

from $75

Chicago City Minibus 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).

4.9

(634)

from $50

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(945)

from $34

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

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

1 hour 30 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.

(2,426)

from $45

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

4.9

(260)

from $59

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

(1,302)

from $30

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

4.6

(577)

from $29

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

(359)

from $37

Private 45-Minute Chicago Skyline Helicopter Tour

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

(134)

from $849

Per group

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.

2-Hour Guided Segway Tour of Chicago

2-Hour Chicago Lakefront & Museum Campus Segway Tour

(497)

from $65

Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Ramin_P, Aug 2026

Relaxed and Great Fun. Incredible sense of freedom.

Michael took very good care of us and was very accommodating on our arrival. Segway lesson was fun and clearly explained. Michael’s tour of Chicago was just right - funny, informative, not too much, not too little. The sense of freedom and ease of movement on the Segways was perfect for a big spacious cityscape - our group of . It seemed pricey at first but we were happy that we had had a good experience and it was well worth it. We would do it again - maybe trying one of the other tours they offer (ours was the Museum Campus). A really good way to see the city.

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!

Field Museum of Natural History Admission Tickets

Ann_W, Jul 2026

Great Half-Day Adventure

Great place to take kids. Very educational and fun! Lots to see for all age groups. We always spend about 4 hours with people who haven’t visited before. The 11 year old was greatly surprised and excited to discover the Pokeman Fossil Museum exhibit! There are some great galleries and as a lacrosse (LAX) family of three players, we totally enjoyed the history of LAX in the area “Native Truths.” There’s a couple virtual reality adventures, Gems and DNA displays, and the historic animals to see. The museum is well worth a visit.

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 CityPASS®

Paul_M, Jun 2026

Save some cash with the CityPass

City Pass is a great way to see Chicago if you know you are going to some of the most popular museums (Field and Shedd) and then allow for some other excursions that you wouldn’t necessarily want to pay full price for (Skydeck, Architecture Cruise) but were still enjoyable and save some cash overall. The Adler Planetarium was a nice find. I would not use for the art institute if you have kids under 13 as they get in for free.