CHICAGO · ILLINOIS
The best of Chicago.
The 10 best 2-hour experiences in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
2-hour small-group Segway tour of Chicago from $65. Learn fast, glide past Millennium Park, Buckingham Fountain, Museum Campus, and the lakefront.
Most Popular“Fantastic tour and Mike is a fantastic guide. I felt safe and secure. Mike chose the absolute best Chicago locations to tour. I will go again many more times.”
A 2-hour Chicago Segway tour with helmet and training, gliding past Buckingham Fountain, Soldier Field, museum campus, and the lakefront.
“Matt was an excellent tour guide. He was warm, welcoming and funny! The segway tour was an absolute blast! Highly recommend!”
A 2-hour private Chicago walking tour customized to your interests, covering Millennium Park icons and public art, with free admissions.
“Leentje was terrific. So knowledgeable, well spoken, and so interesting. She was fun and accommodating (knew where the restrooms were!) made great suggestions for dining, and answered all our questions - really tailored our tour to our interests. I will definitely go on another tour with her.”
Paddle Chicago River downtown on a 2-hour kayak tour with a safety-first lesson, single or tandem options, and skyline views.
“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.”
2-hour Chicago Pier fireworks Segway tour: get trained, glide with a small group, and see Buckingham Fountain and Navy Pier.
“Excellent - went all over the city park areas!”
Walk Chicago’s Loop and Millennium Park with a small-group guide. See the Chicago Theatre, The Bean, Tiffany Windows, and more in 2 hours.
“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.”
Walk Chicago’s Chinatown in 2 hours with a guide: Chinatown Square zodiacs, Pui-Tak Center, Chinese-American Museum, Nine Dragon Wall, Ping Tom Park.
“Very superficial walk through the town. Not much info about the lives of the people or how it was started.”
A private 2-hour Chicago Soul House tour blending neighborhood drive-bys of famous homes with personal stories about Black Chicago culture.
“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!”
A 2-hour Chicago lakefront e-bike loop with expert storytelling, major landmarks, and easy riding from Millennium Park to Northerly Island.
“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!”
A 2-hour small-group Chicago walk with a local guide, popcorn storytelling, and professional photos from Navy Pier to the Water Tower.
“My wife and I got to the pier around 12:20 looked around for about 10 minutes went to meet area never saw our guide nor did we get a msg stating late or no go… went to AMRI Juice bar thing we missed them stayed there until 1:30-1:45pm no cRead more”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
