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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.
“He was very knowledgeable and answer all questions he made the ride interesting and fun! 10/10 recommend when you book ask for Clifton to be your host!”
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
“Great your, Connor was very informative and fun! Went on this tour with my husband who used to live in Chicago and we both learned a lot! We’ve been going down the rabbit hole on a few of the stories Connor mentio...”
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
“Even got cheese caramel popcorn at the Chicago theatre!! Eric was great!!! Fantastic tour: highly recommend & I’m a native Chicagoan!”
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
“The tour was very informative and the stops for photos was great Our driver Rick was very friendly and funny The boat tour was also very informative and the crew was great I would definitely recommend this tour to...”
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
“In addition to visiting several iconic Chicago restaurants and sites and enjoying their delicious specialties, Gabe took us to several sites important to Chicago’s history and architecture.”
Stroll around the Loop with a guide, discovering Chicago's lively food scene, on this small-group walking tour. Learn about the city's history and culinary heritage from your guide as you stop at favorite local...read more
“We loved the sites that we saw from Grant Park, The Stock Exchange, the view of the skyline, Duncan's Toy Chest, the World's largest Starbucks, Lincoln Park, the Chicago River and the Playboy Mansion.”
“Paul, our fearless and fun loving guide, led us on our amazing 3 hour tour by showing us the highlights of Chicago and sharing the historical events telling the incomparable story of a one of a kind place.”
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
“This was my first ride on a helicopter, and it was such amazing experience and there are few reasons for that first one is Pilot Wayne was exceptional, professional and so much fun he made it look so easy to contr...”
“Vincent was the best tour guide- so fun!! Would recommend to my friends!! Have a lot of information about the city and was very mindful of the group”
Expand your horizons in Chicago by gliding along the city’s scenic Lakefront Trail on a fun and smooth-moving Segway. Instead of a long, tiring walk or being confined to a tour bus, enjoy fresh air and flexibility...read more
“Had a wonderful time, our guide was very knowledgeable and a bunch of fun.”
“Finishing the tour right by Navy Pier around 2:00 pm fueled and ready to play, the boys cooled off in a nearby water park, before ending our first day enjoying the Navy Pier and a Riverwalk stroll back to the hotel.”
“Both of the walking tours I have done with Chica-Go walk about were amazing tours lead by a knowledgeable guide!”
Flytographer Private Vacation Photo ShootConnect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best...read more
“Easy for beginners, saw lots of iconic Chicago sites, and learned some interesting historical tidbits.”
“This tour far exceeded our expectations!! Julia was so awesome, she made the trip so interesting and fun! Highly recommend this tour for a great afternoon learning about and experiencing the city!!”
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
“Great tour guide Katrina was very knowledgeable, friendly, and happy to answer questions and involve all the tour members”
Wind & Souls uses the ghosts of Chicago’s past to recreate a city that was and is no longer. Theater fires and the Alley of Death; HH Holmes at home in his murder castle. Chicago has seen it all. From empty tombs to...read more
Get ready to discover the storied architecture of Chicago. You’ll take the first elevator ride of the morning up to Skydeck at Willis Tower to see the city from a birds-eye prime vantage spot. Journey back to street...read more
“Hand picked exteriors and interiors such as London House, Langham Hotel and Chicago Cultural Center will give you an appreciation for the variety and outstanding architectural achievements located within blocks of...”
Welcome to Chicago! Here in the Windy City, we've got outstanding architecture, inspiring public art, a fabulous downtown district, and so much more. Come along with a local guide to check out some of the Must See...read more
“You can tell he loves his city and strives to make the adventure tour something where you can learn about Chicago but also have a fun time.”
This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way!Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour...read more
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along. We are an Austin, TX-based...read more
Are you looking for a way to see Chicago without joining a tour group? Explore at your own pace with this affordable walking tour.• Take in Chicago’s concrete giants and hear fascinating stories about quirky...read more
“Our guide was super fun, friendly and knowledgeable.”
Discover Chicago's bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture. Guests will see iconic...read more