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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 architecture-focused cruise. See all the most important buildings on one tour, a hard-to-accomplish task on foot....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
“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.”
“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
“It was an excellent introduction to Chicago’s unique architecture – great views of the skyscrapers and other buildings from the river level and very interesting guidance by the knowledgeable CAC docent on board –...”
See dozens of landmark buildings that line the Chicago River on the only architecture cruise lead by expert docents from the Chicago Architecture Center. The vessel—Chicago’s First Lady—is designed for prime...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
“This tour was great, very laid back and enjoyable trip down the river.”
“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.”
“You still get the great architectural info on the buildings on the river but also get a great view of the lit up skyline from the lake.”
$2 Mimosas All Day! Sundays are Fun-Days aboard the floating tiki bar. See the Chicago River the Island Party way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax...read more
“Excellent walking tour from the Chicago Architecture Center to the Merchandise Mart.”
Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish...read more
“She is high energy, entertaining, and has a wealth of knowledge and fun facts about Chicago and it's architecture.”
Everyone does a boat tour when they come to Chicago -- it's "the thing to do." But how many people ever get BEYOND that? Imagine all the amazing interiors just waiting to be explored! This 2-hour walking (*not...read more
Enjoy $2 mimosas (all day) and beautiful views of the Chicago skyline aboard our flagship vessel. Enchantment boasts a Tiki Chic vibe, two climate controlled decks, two bars, two bathrooms, premium sound system,...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
Spice up your visit to Chicago on this in-app audio tour through the creepiest places of the city of lights!Explore the most haunted sites and buildings securing tragic and mysterious stories of Chicagoans. Hear...read more
See Chicago Fireworks the Island Party way. Our floating Tiki Bar offers you the unique opportunity to see the sights of the Chicago River, topped off with a fireworks show. Have questions about the buildings you'll...read more
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