The 9 2-Hour Experiences in Chicago That Earn Their Price

1.2-Hour Guided Segway Tour of Chicago

★★★★★★★★★★5.0 · 442 reviews · from $65Our pick

Learn to ride a Segway, then follow a guide such as Mike Artur through Grant Park, Buckingham Fountain, Museum Campus, and the lakefront. Some departures use a Riverwalk route past Navy Pier, Michigan Avenue, Millennium Park, and Chicago’s famous bridges. Groups are limited to eight.

“If you want to explore the "museum campus" this is the tour for you, if you except a tour of the city then you will be disappointed. The description states 2 hour "Tour of Chicago". it was barely 1.5 hours, and we only toured the campus which we had already done the day bRead more”

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2.2-Hour Chicago Lakefront & Museum Campus Segway Tour

★★★★★★★★★★5.0 · 345 reviews · 2 hours (approx.) · from $64

Ride a Segway from Grant Park to Buckingham Fountain, Soldier Field, the Field Museum, Shedd Aquarium, and the lakefront. English-speaking guides such as Kevin, Michael, Colton, Shannon, and Marshall lead small groups of up to eight, with training, helmets, photo stops, and Chicago stories along the way.

“Great staff that made it fun and easy to learn to ride a segway and explore the lakefront and museum campus. Our guide, Marshall, was great! He provided fun facts and history along the tour, offered to take photos, and was always alert to ensure everyone's safety. Highly recommend!”

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3.Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

★★★★★★★★★★5.0 · 35 reviews

Start at Pioneer Court and explore central Chicago with a private CTPA licensed guide for up to six people. Your two-hour walk can focus on architecture, art, food, shopping, or history. Guides including Leentje, Dave, and Mimi offer tours in English, French, or Dutch, with pickup available.

“Our guide Dave reached out prior to learn about what we wanted to do and see. He timely met us at our hotel and gave us a GREAT tour of downtown Chicago including lots of history, facts and places we had not considered including the Read more”

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4.2-Hour Downtown Kayak Rental

★★★★★★★★★★4.5 · 19 reviews · 2 hours · from $62

You’ll receive an English-language paddling and safety lesson, choose a single or tandem kayak, then follow the Chicago River through downtown’s steel canyons. The small group is limited to six, and the dock sits near Chicago transit and downtown sights.

“The person checking us in and giving us our kayaks gave the worst advice on where to kayak. Also, there were so many dead fish and birds floating and a lot of trash. My husband who ended up finishing it and going the opposite way, said it was much better and cleaner.”

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5.2 Hour Chicago Pier Fireworks & Evening Segway Tour

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $77

Ride a Segway through Chicago’s evening parks with a small group of up to seven. After a 15-minute lesson, your English-speaking guide leads you past Buckingham Fountain, Millennium Park, rose gardens, and Crown Fountain to a fireworks view near Navy Pier. Guides Ian and Sean have earned especially strong praise.

“Excellent - went all over the city park areas!”

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6.Downtown Loop & Millennium Park 2 Hour Walking Tour

★★★★★★★★★★5.0 · 5 reviews · from $49

Follow a professional guide from the Chicago Theatre through the Loop to Millennium Park. You’ll see the Marshall Field building, Picasso sculpture, Chicago Cultural Center, Tiffany glass, Millennium Station, and Cloud Gate. The small group is capped at 15, with indoor stops for cold or rainy days.

“I enjoyed the tour. He talked to me about the history of Chicago, and recommended many places. Would go on a tour again in the future.”

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7.2-Hour Chicago’s Chinatown History and Culture Tour

★★★★★★★★★★3.5 · 4 reviews · 2 hours (approx.) · from $30Best value

Walk through Chicago Chinatown with an English-speaking guide, from Chinatown Square and its zodiac statues to the Welcome Gate, Pui-Tak Center, Chiu Quon Bakery, the Chinese-American Museum, Nine Dragon Wall, and Ping Tom Memorial Park. Expect a small group of up to 15 people, free stops, and plenty of photo breaks.

“Very superficial walk through the town. Not much info about the lives of the people or how it was started.”

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8.2 Hour Private Chicago Soul House Tour

★★★★★★★★★★4.0 · 4 reviews · 2 hours (approx.)

Ride through Chicago with a private guide, hearing stories tied to Barack Obama, Michelle Robinson, Muhammad Ali, Ida B. Wells, Muddy Waters, Nat King Cole, and more. Mr. Johnson has been praised for personal care and clear storytelling. Pickup and drop-off are at the Chicago Theatre.

“Mr. Johnson gave us a phenomenal tour and truly took care of u throughout the duration of the tour. Will take additional tours with him next visit to the CHI!”

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9.2 Hour Chicago Landmarks & Lakefront E-Bike Tour

★★★★★★★★★★5.0 · 4 reviews · 2 hours (approx.) · from $72

Ride an e-bike with a guide from Millennium Park to Buckingham Fountain, Museum Campus, Northerly Island, and the Lakefront Trail. Clark or Mike may lead your group, sharing Chicago stories over 7 to 9 mostly scenic miles. The tour ends where it begins.

“Fantastic way to see Chicago! The e-bikes made the ride effortless, and Clark’s energy and local insights made the tour both fun and memorable. A perfect mix of sightseeing and adventure!”

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