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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.
“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
“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...”
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“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
“Very informative and fun! Knowing the details of Chicago's long history of crime was very interesting and seeing the shrine to Frank Nitti was fantastic!”
Chicago has a past filled with big gangster names such as John Dillinger and the infamous Al Capone. Dive deep into the city’s mobster ways with a guide who knows where “the business” was done. Stay comfortable...read more
Named for the cable car turnarounds and the prominent elevated railway that encircled the area at the end of the 19th century, the Loop is Chicago's commercial and cultural core. On today's epic scavenger hunt of...read more
“Great tour guide Joe, lots of good places and gave passengers some decision making ( zoo or Portillo's for food).”
Get a grand overview of Chicago on this half-day tour that ventures beyond downtown to both the North Side and South Side. With included coach transport, you don't need to rent a car or tackle traffic to see...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
“This was the perfect way to get an overview of the city and its sights and get some excellent recommendations for good places to eat and drink!”
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“We had bill and he was the best so Knowledgeable about Chicago history and all of the food we were eating!! Everything was great, big portions everyone was stuffed by the end of the tour!! Highly Recommend this to...”
Chicago's famous food scene is a huge part of its identity but finding the best of all the options can be daunting. Let a foodie-guide show you the way on this culinary-focused tour of the River North neighborhood....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...”
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“He drove us from the Loop, to the Chicago River, up the Magnificent Mile, the Rush Street restaurant area, a children's farm next to the Zoo, the length of huge Lincoln Park, and back along beautiful Lake Shore Dr...”
Check many Chicago landmarks off your must-see list on this small-group sightseeing tour aboard a minibus. Cover more ground than on foot, and hit lots of highlights over the tour. See Museum Campus, the Rookery,...read more
“Very fun and informative, great tour guide, convenient photo op stops.”
PLEASE NOTE: Our mini buses are disinfected after each tour. We will do our best to make each tour fun, informative and as SAFE as possible!Freshly discounted private tours are also available. They will be the best...read more
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“Our guide, Matt J, was really enthusiastic and brought a sense of fun and exploration along with being informative about the city’s history and culture.”
Explore the lakefront districts of Chicago's North Side on a bike tour along quiet streets and waterside paths in the Windy City. You cover ground quickly as you pedal with your guide from Lake Shore Drive to the...read more
Schedule your transfers in advance so you don't have to worry or be late to start your vacation or to begin your business trip.Reliable transportation that you can count on.First class limo/car serviceProfessional,...read more
“I was blown away by our trip to Chicago and Gray Line Tours was the way to see the sights!”
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Schedule your transfers in advance so you don't have to worry or be late to get your business trip or vacation started.Reliable transportation that you can count on.Professional chauffeured-driven in luxury car...read more
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“Tyler was fantastic and did a great job on our tour, We were novices and he was a big help in learning the Segway and getting comfortable.”
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“The guides were fun, knowledgeable and interactive.”
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Don’t miss Chicago’s famous sights (now including Wrigley Field!) and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus,...read more
Schedule your transfers in advance so you don't have to worry or be late to get your business trip or vacation started.Reliable transportation that you can count on.Professional chauffeured-driven in luxury car...read more
Schedule your transfers in advance so you don't have to worry or be late to start your vacation or to begin your business trip.Reliable transportation that you can count on.First class limo/car serviceProfessional,...read more
Choose the number of hours and we can help you make the most out of your time! Book a VIP treatment to see the city in your private car. Our knowledgeable drivers will do the hard work so that you an enjoy the view....read more
Flytographer 90 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do...read more
Flytographer 120 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do...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