Best Sightseeing Tours In Chicago

October 12, 2013 7:00 AM

There’s so much to see and do in Chicago that often the most pressing difficulty with a trip is how to fit it all in. Sometimes it’s easier to just concentrate on where you’re going to experience the great food and cultural entertainment the city has to offer and let someone else take care of showing you the sights. Here are five great tours of Chicago that will ensure that you get a dose of the must-see Chicago areas without going crazy having to decide what to fit in to your already packed schedule.



Architecture Boat Tour
Chicago’s First Lady
112 E. Wacker Drive
Chicago, IL 60611
(847) 358-1330

The Architecture Tour given through Cruise Chicago and the Chicago Architecture Foundation will most likely interest both native Chicagoans and newcomers alike. The tour boats are equipped with both open-air and air-conditioned seating (although seating is general admission and first come, first served) and run about 90 minutes long. Tours are perfect for groups that would rather not do a ton of walking or perhaps just want to relax and absorb the city views from the comfort of a boat cruise after a long day of shopping or sightseeing. The guides are informative and will point out several interesting architectural aspects of the city. The boat is also equipped with a full bar. Discounted tours are available on the website on Tuesdays and Wednesdays and group reservations are also an option.

Untouchable Tour
610 N. Clark St.
Chicago, IL 60610
(773) 881-1195

If you’re interested in learning a little about prohibition-era Chicago and enjoying a little camp humor while you’re at it, the Untouchable Tour may be right up your alley. The tour is two hours (with no stops, so use the restroom before you go) and the guides take you through the gangster-related spots in the city. Think Capone and Dillinger. During the drive between locations, music from the 20s and 30s plays to put you in the mood for the tour. Soak up a little history and have a laid-back and amusing time rolling back through the Roaring Twenties. Tours depart from the Rock N’ Roll McDonald’s and group rates and reservations are available through the website.



Chicago Hauntings Ghost Tour
610 N. Clark St.
Chicago, IL 60610
(888) 446-7891

If you’d like a little insight into the history of Chicago with a ghostly candy shell, Chicago Hauntings Ghost Tours may be your type of candy. Tours depart from the Rock N’ Roll McDonald’s on Clark Street aboard a black tour bus. The guides take you through the known rumored haunted spots of the city, and give you a little Chicago history as told through ghost stories. The infamous Resurrection Mary, the Hull House baby, the Eastland disaster, Fort Sheridan and the St. Valentine’s Day Massacre are all covered, among others. Reservations and private tours are all available through the website.

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Steve’s Segway Tours
155 N. Harbor Drive
Chicago, IL 60601
(312) 946-9467

What better excuse to try out one of those weird Segway contraptions than with a tour around Chicago? Steve’s Segway Tours will take you through a visit of the Chicago downtown lakefront and provide your group with historical and factual information about the notable spots. Not only is a Segway tour a great way to cram in all of those must-see tourist attractions like Buckingham Fountain in one fell swoop, but it’s a great compromise if you have some folks in your group who’d like to be active and walk and some who’d rather take it easy. Those who may be worried about operating the Segway need not fear, the tour guides take the time to train everyone and gives the group a chance to practice before heading out.

A woman walks by the Bank of America in

Joyce Walks Chicago
Chicago, IL
(312) 380-9255

If you’d like a more active tour where you get to walk off some of that great Chicago food that you’re undoubtedly enjoying, try checking out one of the neighborhood tours by Joyce Walks Chicago. The tours are designed to show participants around as if you had a native friend walking you around their favorite neighborhood. Choose any tour from Chinatown to Maxwell Street (see a full schedule of tours here) and make your reservation. Advanced purchase is required and tours often sell out. Private and group tours are also available for booking.

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Meredith Lyons is an actor, competitive fighter and fitness instructor in Chicago who also owns an amazing cat named Jake. Meredith has been writing on Examiner as the Chicago Martial Arts Examiner since 2008. Her work can be found at

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