Top Chicago Segway Tours

2-Hour Chicago Lakefront & Museum Campus Segway Tour

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 & Museum Campus Small Group Segway Tour

Lakefront Segway Tour in Chicago

5.0

(235)

from $70

Special Offer

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

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.

4.9

(52)

from $72

Special Offer

Chicago Sunset 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

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

(10,544)

from $45

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

(3,417)

from $28

Haunted Ghosts & The Chicago Outfit Segway Tour

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

(1,283)

from $30

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.

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

4.9

(255)

from $59

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

(555)

from $29

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

4.4

(937)

from $34

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 30 minutesFree Cancellation

4.8

(16,628)

from $39

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

(130)

from $849

Per group

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

4.9

(621)

from $50

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

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.

(2,383)

from $45

from $144

Top Attractions in Chicago

1 / 2

Attractions

What are people saying about Chicago

Chicago City Minibus Tour

Charles_B, Jul 2026

An informative, fun filled adventure!

Whether you are in Chicago for one day, or for a week or more, this is the trip to take. Our tour guide, who says his name is Trevor, although that could be an alias, lead a fun filled adventure. We saw many historical sites, including the Rookery, the “Bean“, Buckingham Fountain, Soldiers Field, among others, and Trevor had many informative stories about the Windy City, both the good side and the dark side! Incredibly interesting. Trevor also pointed us in the right direction, in regards to other sites and transportation methods we were able to use around the city. It was a very fun time.

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 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.

2-Hour Chicago Lakefront & Museum Campus Segway Tour

Yolanda_M, Jun 2026

Great tour!

I have been on several segway tours over the years and feel like there are less opportunities to explore cities via segway. Fortunately, my husband and I were guided by Kevin in Chicago. After completing the waiver sheets, helmet fitting and training, we were off. We began our tour near Millennium Park and were able to ride through Grant Park and along the Michigan Lake coast. We were able to see some of Chicago’s highlights while having fun. Kevin was always willing to snap a picture of us too. I recommend it!