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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
“Very informative and entertaining - the tour guide Andy was excellent, views were outstanding, bar on board for refreshments and could sit downstairs in the shade when the July sun got too much!”
Explore all three branches of the Chicago River on a journey through the heart of the city. This riverboat excursion introduces passengers to Chicago’s legendary architecture, narrated by a professionally trained...read more
“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
“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
“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...”
“Our "docent" was Nick, and he is a first-class raconteur: very glib, entertaining, personable, knowledgeable, and passionate about Chicago and the marvels of structural engineering that define the skyline.”
Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this...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...”
“Once in Chicago we took a river boat tour that showed us insights of the city that ended up at spectacular Lake Michigan, which allowed us to admire the impressive city skyline as sailors arriving at a mystical land.”
To truly appreciate Chicago's famous skyline, admire it from the water on this top-rated Lake Michigan architecture cruise. While most sightseeing boats remain on the Chicago River, this one gives you a panoramic...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
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
“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
“If you are looking to explore the beautiful sites of downtown Chicago, look no further!”
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
“This was my second tour and It was amazing and really fun.”
Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your local guide, and see alleys, hotels and sites of some of the...read more
“Our guide, Blanca covered all the essentials, architecture, history, culture and nature and did so from the point of view of a Chicago native, who loves her city.”
See the beauty of Chicago from a new vantage point by going on this scenic cruise along the Chicago River and Lake Michigan shoreline. It’s a great way to spot multiple top Chicago landmarks in a short space of...read more
Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax,...read more
On this self guided audio tour, I’ll show you why Milan has more to offer than design fairs and fashion houses. We’ll start at the city’s cathedral, which is its most famous landmark, but from there I’ll help you...read more
Take a grand tour of America the Beautiful with this ultimate bundle of 50 tours across the USA! Relive the intensity of the Battle of Gettysburg. Witness nature’s raw power and beauty at Yellowstone National Park....read more
We wrote the book(s) on Chicago ghosts! Now in our 18th year!Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history over more than two decades. Chicago Hauntings is the...read more
“The walking was easy, the sights were beautiful and Hillary is knowledgeable about the buildings we saw and gave us a lot of background on the history and the architects, along with fun Chicago factoids.”
Discover Chicago of the Roaring '20s thru its Art Deco architecture! We all LOVE the elegance, glam, and glitz of the 1920s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from...read more
If you’ve taken any tour in Chicago, you’ve likely heard some common urban myths masked in “truth” because the tour guide supposedly knows best. But most tours are basically regurgitated scripts that perpetuate...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