Things You'll Need:
- Creative planning
- A reservation
- Good walking shoes
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Step 1
Consult the Chicago Office of Tourism or Convention and Visitors Bureau for city-endorsed tours. Many of these tours cost at least $25 per adult. You do not want to fork over the money for a bad experience. In addition, the city offers free tours with "city greeters" -- insiders with special knowledge of particular neighborhoods or areas which might interest you, such as that brilliant Windy City architecture. The greeters are a great way to get acquainted with the city's lay-out and transportation, especially if it's your first visit.
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Step 2
Since nothing can replace word of mouth, consult friends or colleagues who know the city well, either as frequent visitors or former residents. Chances are, if they were disappointed with their experience you will be, too. Second to their reviews, check out TripAdvisor, a collection of unbiased reviews of hotels, attractions and tours written by tourists who have "been there, done that." You will receive frank feedback before you even book that trip. Consider the source before you receive a second or third opinion on any trip.
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Step 3
Think outside of the conventional box. A number of weird or paranormal tours take you to the city's allegedly most haunted spots. Even though you may believe such things are hogwash, you will still have a good time as these tours delve into the history of the city as much or more so than they do the paranormal. Tours stop at sites such as the infamous Jane Adams Hull House, the location of the St. Valentine's Day Massacre, and less "spooky" locations, such as the sculpture which marked the spot where the Great Fire broke out.
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Step 4
Consider tours that don't involve the conventional mode of transportation. Author Richard Crowe offers supernatural cruises of the city's waterways, river and lakefront. Architectural cruises are also offered. If a cruise doesn't exactly float your boat, look into a Chicago hop-on, hop-off trolley tour, a bike tour or even a tour on Segways like the ones used by police officers across the country.
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Step 5
Try a gut-busting exploration of the city's tastiest foods and restaurants. Even if you miss Taste of Chicago, you can still take a big bite out of all the city has to offer food-wise on a gastronomic tour. There are tours of ethnic grocery stores, chocolate lounges and tea merchants on the high-end Gold Coast area, and even hot dog tours. Skip the ketchup, though. The signature Chicago-style dog is topped with neon green relish, mustard, onion, a dill pickle spear, tomato slices or wedges, sport peppers and a dash of celery salt. You'll get to taste test these dogs, and more gourmet-style ones, on such tours.
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Step 6
Check out tours offered outside of the Museum district and Loop, as many of the most memorable tours are offered outside of the typical tourist haunts. For example, guides offer insight into Chinese immigration in Chinatown. A diverse array of neighborhood-specific tours are also offered year-round. Trying to get in touch with your Italian roots? How about the Little Italy tour, which also includes a stop at the historic Hull House. You name your interest, and there is sure to be a walk that's right for you.
