Many visitors like to eat typical Chicago-style foods. Some of the most popular choices are deep-dish pizza (thick with lots of cheese), Italian beef (dipped in beef juice until the bread is soaked) and the hot dog (mustard, not ketchup). I cannot say that there are consensus choices for which restaurants have the "best" ones, as many locals have different favorites.
There are many Italian, Mexican, Chinese, Korean, Polish and Mediterranean restaurants in Chicago.
The annual Taste of Chicago is held in Grant Park over the July 4th holiday. Sure it is overcrowded and touristy, but it is fun to try weird ethnic foods and Chicago favorites.
Quick Tips:
Most visitors will hang around the downtown area and its adjacent neighborhoods (the Loop, River North, Gold Coast, South Loop, West Loop). While there are certainly good dining choices here, some prefer to venture a bit farther for food. Some popular areas a bit further out with a good selection of restaurants are Wicker Park, Bucktown, Lincoln Park, Lakeview, Andersonville, Hyde Park and Chinatown.
The downtown area contains or is within walking distance of zillions of attractions, hotels and restaurants. I am always asked if walking in downtown is "safe". Indeed, the big bad city may intimidate the untrained visitor with its urban attitude. However, I always say that as long as you use common sense (for example, do not count your stash of cash in the middle of a busy street), you should have no problems wandering about Chicago. Walks along the lakefront and down Michigan Avenue are essential to any visit in Chicago.
Best Way To Get Around:
I complain about the CTA (public transportation system of buses and "L" trains), but I still ride it every day. While I may unfairly compare it to exemplary public transportation systems elsewhere in Europe and Asia, the CTA is on the whole a reliable and comprehensive system. If you are hanging around downtown, there are many useful bus and L routes that you can use. Get a CTA transit card that is good for all-day travel for one to five days. The L routes are handy to get to some of the more far-flung attractions, and you have direct access to both airports (Blue Line to O''Hare, Orange Line to Midway). There are also various downtown trolley services (some free, some part of a tour) that are geared to tourists.
If you enjoyed my reviews on Chicago dining, please take a look at my accompanying articles: "Bill at home in CHICAGO - Activities" and "...Accommodations".
I would like to thank my colleague, Chicago architect Marius Ronnett, for sharing many of his stunning images of his adopted hometown.