9 2-Hour Experiences in Chicago Worth an Afternoon

1.2-Hour Guided Segway Tour of Chicago

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

Spend about two hours on a guided Segway ride through downtown Chicago. After a short lesson and safety gear fitting, a group of no more than eight follows either a Grant Park and Museum Campus route or a Riverwalk route past Navy Pier, the bridges, Michigan Avenue, and Millennium Park. Guides have included Mike and Captain Segway.

“It was a great tour, Mike Artur guide was awesome funny and very informative. We would totally recommend it”

Check availability →Read our full review

2.2-Hour Chicago Lakefront & Museum Campus Segway Tour

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

This two-hour Chicago Segway tour covers about seven to eight miles, from Buckingham Fountain and Soldier Field to the Field Museum, Shedd Aquarium and the lakefront. You get a helmet, practice time and a guide who shares local stories. Groups are capped at eight, and riders must be at least 12 and meet the weight limits.

“Kevin our tour guide was AMAZING!!! I highly recomend this tour, this is a must to do when visiting Chicago..”

Check availability →Read our full review

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

★★★★★★★★★★5.0 · 35 reviews

Set out from Pioneer Court with a private guide for a two-hour Chicago walk tailored to your interests. The route can focus on architecture, art, food, shopping, or city history, and may include Millennium Park’s Cloud Gate, Crown Fountain, and landmark sculptures. Guides have included Leentje, Dave, and Mimi. The $220 group price covers up to six people.

“Dave was very friendly, knowledgeable and easy going. He took us to sites we had walked by many times without knowing the history. Our 18 year old was fascinated by the tour as well.”

Check availability →Read our full review

4.2-Hour Downtown Kayak Rental

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

At the downtown Chicago River dock, Wateriders Kayak Tours & Rentals provides a paddling lesson, safety briefing, and a two-hour kayak rental. Choose a single or tandem kayak, then paddle among the city’s skyscrapers. The group is limited to six, and the activity is led in English.

“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

5.2 Hour Chicago Pier Fireworks & Evening Segway Tour

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

In two hours, a guide leads a small group of up to seven from Segway training to Buckingham Fountain, Millennium Park and a lakeside fireworks view near Navy Pier. You’ll see illuminated park sights, including Crown Fountain, and may hear from guides such as Ian, Sean or Russell. Helmets and a 15-minute orientation are included.

“Increíble experiencia! El tour muy divertido. Las vistas muy lindas. Nuestro guía Sean espectacular! Valió la pena muchísimo!”

Check availability →Read our full review

6.Downtown Loop & Millennium Park 2 Hour Walking Tour

★★★★★★★★★★5.0 · 5 reviews · from $49

Spend about two hours walking from the Chicago Theatre through the Loop to Millennium Park. Your guide covers Chicago’s history and architecture, with stops for the Picasso sculpture, Tiffany glass, and Cloud Gate. The group is capped at 15, and indoor stops are included for cold or rainy weather. No guide name is provided.

“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

7.2-Hour Chicago’s Chinatown History and Culture Tour

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

Spend two hours with an English-speaking guide exploring Chicago’s Chinatown, including Chinatown Square, the Pui-Tak Center, the Chinese-American Museum, the Nine Dragon Wall, and Ping Tom Memorial Park. The small-group walk is capped at 15 people and costs $30 per person, with a souvenir included.

“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

8.2 Hour Private Chicago Soul House Tour

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

Spend about two hours on a private Chicago drive past homes associated with Barack Obama, Michelle Robinson, Muhammad Ali, Louis Armstrong, Ida B. Wells, and others. Your English-speaking guide shares personal insight and anecdotes. Pickup and drop-off are at the Chicago Theater; the vehicle is air-conditioned.

“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!”

Check availability →Read our full review

9.2 Hour Chicago Landmarks & Lakefront E-Bike Tour

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

In two hours, ride 7 to 9 miles from 300 E Monroe St through parkland and along Chicago’s lakefront to Buckingham Fountain, Museum Campus and Northerly Island. Your guide shares local architecture, culture and history as you pass major museums and Soldier Field. E-bike and helmet are included, and the group is capped at 10.

“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!”

Check availability →Read our full review