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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.
“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
“This night tour was very interesting for people who want to learn about Chicago history, gangster history and the overall tenor of the times between late nineteenth century and mid-twentieth century.”
Sightseeing in Chicago is especially entertaining with this nighttime crime history tour. A guide aboard the bus details the Windy City’s notorious mobsters, from Al Capone to Bugs Moran. It’s a fun and...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
“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
“What a great Wayne to discover the City This tour allowes you to explore other part of the city Thank to Kevin we had a great lesson of history He was a good entertainer, great energy and interesting knowledge of...”
Chicago offers amazing historical and culinary adventures, and this bike and food tour allows you to experience both while leaving the navigation to a guide. Hop on a provided bike and pedal around 13 miles (21...read more
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
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
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
Flytographer 60 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
Working up an appetite won’t be a problem on this tour! We’ll be sampling from Chicago’s well known food staples -- pizza, hot dogs, and Italian beef. You’ll learn the history behind the foods and also get a taste...read more