Gangster Tour
Perhaps one of the craziest times in the history of Chicago was the 1920s and 1930s, when gangsters virtually ran the place. Al Capone, John Dillinger and many others helped to build the reputation of the city as a haven for outlaws and prohibition-era partying. Of course, many of them died violent, bloody deaths. And you can relive it all with Untouchable Tours. Untouchable Tours offers a two-hour ride through the rough streets of Chicago as it was during gangster days. You'll learn all about the famous hideouts, brothels, underground gambling dens and legendary shootouts, all through the help of costumed character guides who offer a lively recounting of gangster tales. Tours run daily at 10 a.m., with additional times that vary by day and season.
Untouchable Tours
North Clark St.
Chicago, IL 60643
(773) 881-1195
gangstertour.com
Weird Chicago Tour
The Weird Chicago Tour was born in 2006, the brainchild of a guy who just loves history and mystery. The thing about the Weird Chicago Tour is that it's not just one kind of tour but rather offers a range of new ways to enjoy Chicago. There are the obligatory ghost tours, some on a three-hour bus ride and some on foot. Then there are the serial killer tour, the Chicago sex tour and the public enemies tour. Tours are available year round, and the ghost tour, fittingly, starts at 7 p.m. so you can take in the spooky sights in the dark.
Weird Chicago Tour
63 W Ontario St.
Chicago, IL 60654
(888) 446-7859
weirdchicago.com
Tall Ship Windy
If you've never been on a tall ship, you're in for an interesting time. But when you take a ride on Windy or Windy II, you never get the same tour twice. That's because the boats are at the mercy of the wind, so the captain's only course is that which the wind provides. If you want extra strange, take the Real Pirates of the Inland Seas tour, where you can learn about the past pirates of the area and the defenders of the shore. You can also help raise the sails, or you can just go along for the ride...wherever it takes you. The ship sails from Memorial Day through the end of September, from 11 a.m. until midnight.
Tall Ship Windy
401 E Illinois St., Suite 332
Chicago, IL 60611
(312) 731-9689
tallshipwindy.com
About The Author
Patrick Cameron is a freelance writer with 10 years of diverse experience in consumer goods branding, promotions and retail communications. He works out of his home in Denver, Colo. He received his Bachelor of Arts in mass communication from the University of Minnesota.