Chicago · 2-HOUR EXPERIENCES
Every trip has one free afternoon too few. These 11 2-hour experiences justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
2-hour small-group Segway tour of Chicago from 2 E 8th St. Learn to ride and glide past Millennium Park, Buckingham Fountain, and more.
“The great stories were entertaining and the old airport nature preserve was a beautiful surprise! Thank you Mike!”
Ride a Segway through Chicago’s lakefront and Museum Campus on a small-group, 2-hour tour with helmet training, live guide commentary, and great photo stops.
“Shannon was a great tour guide. He was energetic, was patient with us, and offered to take some photos of me and my partner”
A private 2-hour walking tour in Chicago tailored to your interests, covering Millennium Park public art like The Bean and Cloud Gate.
“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.”
Kayak the Chicago River downtown for 2 hours with a safety lesson, single or tandem boats, and skyscraper views for $62.
“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.”
Glide Chicago at night on a segway, then watch Navy Pier fireworks with big views of Buckingham Fountain and Millennium Park.
“Increíble experiencia! El tour muy divertido. Las vistas muy lindas. Nuestro guía Sean espectacular! Valió la pena muchísimo!”
Walk the Loop’s architectural icons and Millennium Park highlights in 2 hours, with indoor stops in bad weather and great photo spots.
“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.”
2-hour Chinatown History and Culture Tour in Chicago with murals, dragon walls, Pui-Tak Center, a museum, and Ping Tom river views.
“Very superficial walk through the town. Not much info about the lives of the people or how it was started.”
A 2-hour private Chicago Soul House tour with pickup and narrated stops tied to Black icons, from Obama to Muddy Waters.
“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!”
Ride an e-bike along Chicago’s lakefront to see Buckingham Fountain, Museum Campus, Northerly Island, Adler, and Shedd in about 2 hours.
“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 Chicago highlights walk with a local guide, popcorn stories, and professional photos, starting at Navy Pier.
“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”
Rent a kayak for 2 hours on Chicago’s Bubbly Creek from Bridgeport. Spot wildlife, enjoy calm water, and learn stockyard history for $48.
Every kind of day out in the city, and the best of each.
