The 5 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”

Check availability →Read our full review

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!”

Check availability →Read our full review

3.2-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.”

Check availability →Read our full review

4.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.”

Check availability →Read our full review

5.2-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.”

Check availability →Read our full review