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735 reviews
Chicago has a past filled with big gangster names such as John Dillinger and the infamous Al Capone. Dive deep into the city’s mobster ways with a guide who knows where “the business” was done. Stay comfortable...read more
Taking safety measures
1–2 hours
from US$45.00
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46 reviews
Sightseeing in Chicago is especially entertaining with this nighttime crime history tour. A guide aboard the bus details the Windy City’s notorious mobsters, from Al Capone to Bugs Moran. It’s a fun and...read more
Taking safety measures
2 hours
from US$50.00
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9 reviews
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
Taking safety measures
2–3 hours
from US$43.95
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128 reviews
Explore the lakefront districts of Chicago's North Side on a bike tour along quiet streets and waterside paths in the Windy City. You cover ground quickly as you pedal with your guide from Lake Shore Drive to the...read more
Taking safety measures
3 hours
from US$46.99
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239 reviews
Chicago offers amazing historical and culinary adventures, and this bike and food tour allows you to experience both while leaving the navigation to a guide. Hop on a provided bike and pedal around 13 miles (21...read more
Taking safety measures
4 hours
from US$79.99
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36 reviews
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
Taking safety measures
3 hours
from US$45.99
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10 reviews
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Taking safety measures
2 hours
from US$108.66
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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
Taking safety measures
2–3 hours
from US$250.00
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1 review
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30 minutes
from US$272.44
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1 review
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you...read more
1 hour
from US$200.00
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Flytographer 90 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do...read more
1–2 hours
from US$544.88
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Flytographer 120 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do...read more
2 hours
from US$708.34
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Flytographer 60 Minute Vacation PhotoshootConnect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do...read more
1 hour
from US$350.00
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1 hour
from US$294.98
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