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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.
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
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
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
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
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
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
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
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic...read more
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
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
Enjoy a private 2-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English,...read more
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 is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you...read more
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
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
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
Alley Kat Adventures is an Austin, TX-based event design company offering city scavenger hunts in 30 cities in the US and Mexico as well as custom events worldwide. Our specially hand-crafted, interactive quests are...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