I can think of three restaurants with free parking. They are all in Hyde Park. There is only one theater there, but I highly recommend it: The Court Theatre--it alsoi has free parking:
The restaurants are: La Petit Follie http:lapetitfollie.com
The Cedars of Lebanon: http://www.eatcedars.com
Piccolo Mondo: http://chicagometromix.com/restaurant...
1642 E 56th St Ste 1, Chicago, IL 60637
I assume you're going to one of the theaters in the Loop. The only restaurant in the Loop I'm aware that offers free parking is Everest. Everest also has a nice pre-theater deal for 5:00/5:30 seatings, with a set three-course menu for around $50. www.everestrestaurant.com
Otherwise, you'll have to pay for parking. As ferret notes, if you eat close to the theater, you'll only have to pay once. Some restaurants may have arrangements for valet parking including theater hours - not free, but not excessive. You can find recommendations for restaurants near the Chicago, Oriental, and Cadillac Palace theaters in the Loop in these topics:
There's a website covering downtown Chicago on which you can enter the address you're going, and what time you're arriving and departing, and it shows you the rates for parking at all the garages/lots in the vicinity. I use it all the time and it's great; it's amazing how much rates can vary among garages within a few blocks of each other. It's http://chicago.bestparking.com/index....
Wow. Great site! Thanks. Actually, the theaters we go to aren't limited to the loop. There are all kinds of great "black box" smaller theaters that we love. The restaurants don't necessarily have to be near the theater. We like to try different neighborhoods. Ina's in the west loop has a parking lot, and I was just wondering if there were others. Thanks.
As I recall, the valet parking at Greek Islands is free, although you still should of course tip. Otherwise Ferret's suggestion is a good one. A number of restos in the Loop Theater area have a single rate for parking for both dinner & the theater - I know that Trattoria No. 10 does that.