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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
“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
“very informative cruising up and down the Chicago river...and then the highlight....passing through the lock out on to Lake Michigan.Very fun! Followed by a wonderful time out and back viewing the city skyline!”
If your feet need a break from the city streets, a short sightseeing cruise is the perfect way to see the best of Chicago without breaking a sweat. Offered regularly throughout the day, it’s easy to fit this tour...read more
“He drove us from the Loop, to the Chicago River, up the Magnificent Mile, the Rush Street restaurant area, a children's farm next to the Zoo, the length of huge Lincoln Park, and back along beautiful Lake Shore Dr...”
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
“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
“If you’re looking for a good time with friends and family, The Spirit of Chicago is the way to go! Great food, great drinks, music, fabulous views, and an outstanding crew!”
This Chicago dinner cruise allows you to see the sights, have fun, and grab a bite to eat all in one evening. An all-you-can-eat buffet, onboard DJ playing dance favorites, and sunset views of Chicago from Lake...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
“Segways are a Blast to ride and a Great way to experience the Second City Lakefront with a knowledgeable guide to make it informative, interesting, and fun! Shout out to our guide Pat who was fantastic!”
Explore Chicago's Museum Campus in record time on a Segway, enabling you to cover more ground in less time when compared to walking. All Segway training and equipment are included, making this tour accessible to...read more
“We had wonderful weather that day and I enjoyed the nice paved trail, views of the lake, and the stops where we looked at different attractions.”
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
“The evening tour was enjoyable and relaxing as the crowds had mostly gone home, and we enjoyed the beautiful views and sights along the lakefront and watching the fireworks from the museum campus.”
“Tyler was fantastic and did a great job on our tour, We were novices and he was a big help in learning the Segway and getting comfortable.”
“Matt was an awesome tour guide & riding the Segway was easy after a brief one-on-one instruction.”
This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a chance to ride Electric Bikes and see the city from a...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
“The guides were fun, knowledgeable and interactive.”
“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
“Sean was great at teaching us how to operate the Segways and made sure every part of the tour was fun, educational, and safe.”
Not only will you receive a safe and scenic guided tour through the city, your guide is an excellent resource to answer those questions you may have about biking the streets of Chicago or the history of a...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
There's no better way to tour the world-class city of Chicago than on a Segway! On your very own private tour, we will cruise around the parks and along Michigan avenue and show you the best that Chicago has to...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
Our Chicago Foodie Lovers Tour will take you to the most iconic and delicious spots in Chicago all in one day. If you are looking for a little bit of culture, great photos, and a ton of delicious food then this is...read more
If you're looking for an exciting and stress-free day exploring the wonders of Chicago, then this is the tour for you. We can’t wait to show you around!The morning will start with a private pickup from your hotel by...read more