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Tours, activities and experiences bookable on Tripadvisor, ranked using exclusive Tripadvisor data including reviews, ratings, photos, popularity, user preferences, price, and bookings made through Tripadvisor.
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Tours, activities and experiences bookable on Tripadvisor, ranked in alphabetical order.
“Amazing tour full of fascinating facts and information about The Chicago theater history and architecture.”
“Our tour guide was Dylan and he was excellent, very informative tour and his jokes gave the tour a relaxed and enjoyable feel- would recommend this tour if you’re visiting the city!”
Combine a Chicago history lesson with supernatural tales for an ideal activity for adults and kids. Go back in time on the Gangsters and Ghosts tour to hear about Chicago in the roaring 1920’s when speakeasies...read more
“The night tour was great and James was an amazing tour guide who did all these extras to make the ride fun, like light strings and a bubble gun! Perfect views during the day and at night!”
Known as a world-famous hub for architecture, art, and politics, the lakeside city of Chicago has a wealth of must-see sights. Know exactly where to go in the Windy City on this hop-on, hop-off bus tour, complete...read more
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you...read more
“Walking pace between food stops was just right, food choices were scrumptious, and history narratives, views of the river, architecture, and choice of stops superb!”
Combine tastes of Chicago's most famous foods with stops at local must-see landmarks on a single tour. Instead of spending the day chasing down these foods and highlights on your own, save valuable vacation time by...read more
“This tour offered a local perspective of Chicago so it totally didn’t feel like a scripted tour at all. Kelly gave us interesting and unique facts about Chicago’s architecture and transportation and history, even...”
“Chicago Architecture River Cruise 2) 360 Chicago (former John Hancock Building) 3) Art Institute of Chicago 4) Hop-On Hop Off Bus Tour We purchased this option as it gave us 1 additional choice compared to the reg...”
Discover the Windy City your way with a Go Chicago Explorer Pass. Valid for 60 days, the pass is ideal for travelers who want to take their time exploring the city. You can visit top attractions such as the SkyDeck,...read more
“I got a great handle on what makes Chicago Chicago, while also learning about the buildings, the hiatory, the food traditions and comfort food of locals, and plenty of insight into the life and mindset of the ever...”
“I was blown away by our trip to Chicago and Gray Line Tours was the way to see the sights!”
“We had wonderful weather that day and I enjoyed the nice paved trail, views of the lake, and the stops where we looked at different attractions.”
Get close to Chicago's most important monuments and parks on a top-rated bike tour that travels entirely on the city’s abundant bike paths, so there's no need to worry about traffic. Pedal through Grant Park, along...read more
Downtown Chicago is filled with gems. Some famous, others known only by select locals. Many of these spots are best seen on foot as opposed to a moving vehicle. We'll take you inside several of these architectural...read more
Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then...read more
If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around!The morning will start with a private pickup from your hotel by...read more