CHICAGO · ILLINOIS
The best of Chicago.
The 15 best city tours 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.
Chicago Loop walking donut tour with multiple bakery stops, landmark sights, and included samples for a sweet meal. Vegan options available.
Most Popular“It’s a fun fact filled tour and a great way to experience several types of donuts and learn the history.”
Small-group Chicago architecture tour by minibus, with optional open-top river cruise. Hit the Loop, skyline views, and top icons fast.
“Best tour ever!!! Avery was FANTASTIC!!! I could have ridden around with him for hours hearing about the city. Hate that it only lasted 2 hours! He really knows his history and was able to answer every question I threw at him! Trevor give this man a raise! He was awesome and I would book…”
Seadog speedboat from Navy Pier blasts along Lake Michigan with a live guide, skyline views, and optional Extreme Thrill spins.
“The access was very expeditious and the tour itself was so fun!”
See Chicago highlights in 2 hours on an air-conditioned minibus with live narration, key photo stops, and easy downtown pickup.
“This was a great tour with wonderful historical facts anf photo opportunities. It was a perfect opportunity to see the sites while staying out of the freezing temperatures.”
A 2-hour small-group lunch cruise on Lake Michigan from Navy Pier with buffet lunch, DJ entertainment, and skyline views.
“This was for my boyfriends birthday. We came here from DC. This was a ball. The DJ was on point!! The food was amazing! Salmon, Chicken, veggies, pasta, salad.. A table of sweets! The customer service was A1! Everything was a beautiful time! Make sure you go upstairs and hangout!”
A 75-minute Seadog speedboat architecture cruise from Navy Pier. See Chicago River landmarks and Lake Michigan sights with live narration.
“This boat ride was lots of fun and very informative! Our guide, Andrew, was knowledgeable and very funny! This was the best way to see Chicago.”
A 3-hour Chicago bike tour for $59, riding mostly bike paths along Lake Michigan and major museums, with time for photos and stories.
“Bike tours are an excellent way to explore new cities/places. Having a great tour guide is important and Meredith is the best. She is knowledgeable, fun and perky! Bikes were in good shape and helmets clean.”
Lake Michigan lunch or dinner cruise from Navy Pier with a big buffet, live DJ, rooftop games, and skyline views. Brunch includes bottomless mimosas.
“The whole experience was wonderful for my husband & I.”
Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.
“The bean and Wrigley field. Buying cub jerseys personalized. The skyscraper view at navy pier. Chicago university.”
Climate-controlled minibus tour of Chicago’s key architecture with three photo stops, plus optional 75-minute river cruise.
“Informative as well as humorous - good driver - good way to see downtown highlights as well as the nice area near Lincoln Park. Highly recommend.”
A $32 small-group Chicago ghost tour through Lincoln Park, with stop-by-stop true crime and haunting stories for a spooky one-hour walk.
“Elliot’s tour was amazing!! It was so cool to learn more about the history and ghost stories of Lincoln Park!”
A 2-hour Chicago food walk through the Loop, Riverwalk, and iconic classics, with enough tastings for a real meal and plenty of local tips.
“Brilliant tour and the guide really tailored it to our family. Great way to enjoy Chicago. Was very full up by the end. With food and knowledge.”
Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.
“I had a great time on this walking tour. Just fyi there is another sign up if you want to add the food walking tour. First tour is 3 hours, second is 2. Our guide did an amazing Job. You could tell he was very passionate about his city. We had about 12 people on…”
City Cruises Chicago River brunch, lunch, or dinner pairs a 3-course meal with glassed-in skyline views and optional narration, DJ, and mimosas.
“Food is excellent!!!! I was running late and they still allowed me on! I would most definitely come here again and worth every single penny. A must do!”
A Chicago Lake Michigan fireworks dinner cruise with a buffet, DJ, and Navy Pier views. Smart casual, weather-dependent fireworks, great value.
“The staff worked extremely hard throughout the cruise to make our experience memorable. Kudos to your team!”
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.
