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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.
“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
“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
“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
“Dave was excellent in providing a personable and unscripted view of Chicago’s history including architecture, development, arts, ethnicity, and the all important food & drink.”
“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
“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...”
“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.”
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
“Fun foods that will fill you up....we weren't hungry for dinner until about 10 pm! Kelly was a great guide providing her knowledge of the restaurant scene and Chicago lore as we walked between classic food destina...”
“The tour gave me an excellent introduction, including comparisons to what came before, the ideology that was foundational to this approach, political forces that supported the modernist building boom in Chicago, a...”
“Easy for beginners, saw lots of iconic Chicago sites, and learned some interesting historical tidbits.”
“Sarah will teach you how to ride in minutes, and then off you go on an architectural tour of the city along with the sights of Grant Park, the Riverwalk, and the Chicago Shoreline.”
“We enjoyed a peaceful scenic tour down the river with the sun light touching the shimmering glass of the skyscrapers at just the right moment.”
“Interesting information and beautiful views of the Chicago skylines and architecture Definitely would recommend”
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic...read more
Are you looking for a way to see the wicked city without joining a tour group? Explore at your own pace with this affordable walking tour.• Find the city’s dark side with stories of opium trade, the city’s first...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