Monday, October 12
In honor of the Italian restaurant’s eighth anniversary, Osteria La Madia (59 W. Grand Ave., River North, 312-329-0400) offers a lunch special today through Saturday. For $8, you can get the chef’s choice of pasta as well as your selection of soup or salad. Can’t make it this week? The restaurant will have new weekly specials for the rest of the month, too.
Friday, October 16
Buy crab (or fish, or steak, or any entrée at all), get crab free at the venerable Hugo’s Frog Bar & Fish House (1024 N. Rush St., Gold Coast, 312-640-0999). Called the Practice Crack, this event provides a chance for staffers to warm up for the start of stone crab season. They’ll hand out gratis medium claws starting at 3 p.m. while supplies last.
Saturday, October 17
Speaking of free food: If you find yourself starving in Lincoln Square at midnight tonight, you can head to Taco in a Bag (4603 N. Lincoln Ave., Lincoln Square, 773-250-2437). Every Saturday night in October from midnight to 1:30 a.m., the self-explanatorily named spot will offer an all-you-can-eat special on its namesake item. There will be a new iteration each week starting with tonight's Angry Bird, a verde-braised chicken thigh taco with queso fresco and garlic-infused sour cream.
Sunday, October 18
The Bears take on the Lions at noon today, and starting at 11:30 a.m. you can tailgate on the all-season rooftop at the J. Parker (1816 N. Clark St., Lincoln Park, 312-254-4747). The place will serve brats with pickled onions and beer mustard, Frito-spiced pork rinds, and deals on buckets of beer ($20 for craft options from such makers as Atlas Brewing Company and 4 Hands Brewing Co.).
Another longtime spot celebrates a birthday this week: the nine-year-old Katherine Anne Confections (2745 W. Armitage Ave., Logan Square, 773-245-1630). Starting Sunday, the café will offer special anniversary truffles (coffee-citrus-hazelnut, a combo of three of the shop’s original flavors) for free with any $10 purchase as well as packs of five caramels for $1. On Sunday only, guests in the shop will get a free shot of drinking chocolate with housemade marshmallows and toppings of their choice.