Chicago · CITY TOURS
This is the shortlist you would send a friend: 11 city tours worth the money, each with its price, its traveller verdict and the one thing to know before you commit.
Ride a climate-controlled minibus through the Loop, Gold Coast, Lincoln Park, and Museum Campus with guides such as Avery, Rick, and Reenie. Add a 75-minute Chicago River cruise for close views of iconic buildings and the story of the river.
“Very informative and an excellent guide on our walk. So much to learn and absorb about your city..thanks Jennifer”
Explore Chicago by private vehicle with a guide and driver, stopping at Millennium Park, the Loop, Lincoln Park, Hyde Park, the University of Chicago, and Wrigley Field. Guides such as Todd, Mike, Matt, and Scott tailor the route to your interests, while downtown hotel pickup keeps the morning simple.
“The guide was super knowledgable and the driver was so smart about which route would get us safely to our destination. We did this tour as soon as arriving to Chicago and we are so glad we did! Thanks for helping to make our Chicago trip memorable!!!”
Ride Chicago’s L with a certified guide and a group of no more than 10. You will spend only about 15 minutes on the train, with most of the two-hour tour outdoors at stations, viewing Chicago landmarks and learning how the city grew around its rail system.
“Steve our tour guide was great, very professional and knowledgeable and great stories about the history and characters involved in building the elevated system. I would highly recommend this tour.”
You’ll tour Chicago by air-conditioned vehicle with bottled water, snacks, and an English-speaking guide. Ilyas and the team cover major sights from Millennium Park to Hyde Park, with photo stops, hotel pickup for a fee, and groups capped at 10. Expect a fast, full day rather than long visits inside attractions.
“Very good experience My initial tour was fully booked but the tour operator did not cancel; instead, they gave me an alternative for a more private and luxury experience. Very beautiful and comfortable car Full explanation All spots And they took me all photos also!”
You’ll tour Chicago in a private, air-conditioned vehicle for 2 to 8 hours with a guide such as Cavani or Ilyas. Expect flexible pickup, city highlights, architecture, lakefront views, snacks, water, parking, and time for souvenirs. Attraction admission is generally extra.
““E” our driver was prompt friendly And very knowledgeable. He made sure we hard the best experience in our 6 hour time. We explored all around Chicago and inside may buildings looking at the architectural design. I would highly recommend this…. Thanks “E””
Travel from Chicago to Milwaukee with an English-speaking guide in a group of up to 14. Visit the Harley-Davidson Museum and Miller Brewery if selected, browse the Public Market, and see the lakefront and Milwaukee Art Museum. Guide Nico is one named guide associated with the experience.
“Personal service was great Nico our guide and driver was excellent and very helpful. No need to change anything”
Spend about three and a half hours seeing Chicago from two useful angles: a guided downtown minibus ride and a 90-minute Chicago River architecture cruise. Joseph has led the bus tour, while the boat guide explains the city’s famous buildings. Expect short walks, photo stops, bottled water, and free Starbucks coffee onboard.
“Great tour, great value for the cost. Wish the bus ride longer than the boat ride. Bout ride heavy focus on architecture. Bus ride spoke on the history of Chicago, much more engaging!”
Travel from Chicago to Milwaukee in a small group of up to 14 people, with stops at the Harley-Davidson Museum, Milwaukee Public Market, Miller Brewery, lakefront, Art Museum, and City Hall. Choose a basic city tour or add museum and brewery admissions when booking.
“The Milwaukee Art Museum was a visual masterpiece—its stunning architecture and lakefront setting made for the perfect introduction to the city’s creative spirit. Inside, the collection was diverse and thoughtfully curated, with something to capture every kind of art lover. The Milwaukee Public Market was a lively and delicious stop. From artisan cheeses to fresh-baked pastries and handmade crafts, it had the kind of local charm that made it easy to lose track of time. I’d also like to highlight the exceptional service provided by our tour guide. He is knowledgeable, friendly, and kept everything running smoothly without ever making the day feel rushed. His insights added so much to…”
Start at Millennium Park with Cloud Gate, then see Grant Park, Michigan Avenue, landmark buildings, and Chicago's skyline from 360 Chicago. Depending on the departure date, add the Art Institute, an architecture cruise, or a 100-minute exterior architecture tour. Guide Momo can assist with tickets and reduced walking.
“Momo was so kind to us. She got tickets for us and dropped us off where we could have easy access to attractions. We have some mobility issues and Momo helped minimize any excess walking. Great day of all the highlights.”
See Chicago’s best-known sights in about two hours by luxury minibus, with stops at Palmer House, Museum Campus, Buckingham Fountain, and the Rookery Building. Guides such as Avery and Logan add facts, humor, and local context while you ride past Soldier Field, the Field Museum, Millennium Park, and the Magnificent Mile.
“Filled with fun, obscure facts and the traditional tour details. Avery was personable, knowledgeable and downright funny at times.”
See Chicago at its most festive with a private guide and driver, including the Magnificent Mile, Christkindl Market, Macy’s Walnut Room, Millennium Park, Solidarity Drive, and Lincoln Park Zoo Lights. Pickup is offered downtown, and the comfortable vehicle keeps winter weather at bay.
“Matt and Vick were AMAZING!! The diversity, knowledge, and understanding was one of a kind and know I couldn't find it anywhere else. It was chilly out today but the vehicle was warm and comfortable. The uniqueness of Chicago which makes this city so monumental and the truth inside the bean! We are so happy we took those tour and blessed Matt and Vick were our tour guides and driver!”
Pick a river, a sidewalk or a plate.
