Monday, October 26
Smoke and sip at Fountainhead’s (1970 W. Montrose Ave., Ravenswood, 773-697-8204) Cigars & Whisk(e)y event, where a $15 ticket gets you a one-and-a-half-ounce pour of the brown stuff and a cigar to enjoy on the bar’s rooftop starting at 7 p.m.
Claw into Alaskan king crab at Del Frisco’s (58 E. Oak St., Gold Coast, 312-888-2499), available for the next two weeks only. The seasonal specialty will run for $55 a pound (and $27.50 a half pound).
Thursday, October 29
Attention tequila fiends: Meet master distiller and Tequila Tromba founder Marco Cedano over a $100 four-course dinner at Naha (500 N. Clark St., River North, 312-321-6242), with beverages featuring the booze whipped up by the spot’s bar director, Amy Starr. Call the restaurant to make a reservation. Dinner starts at 6:30 p.m.
Saturday, October 31
Rebar (401 N. Wabash Ave., River North, 312-588-8034) will rebrand itself as Reboo tonight, but don't be scared—it's just for a Halloween party. The $25 entry includes a specialty cocktail and a chance to enter a costume contest. There are also open-bar and dinner packages should you wish to go all out. More info available here.
You can still buy tickets for the 9 p.m. seating of Kill Grill, a Tarantino-inspired izakaya dinner at Fat Rice (2957 W. Diversey Ave., Logan Square, 773-661-9170). The multi-course menu takes its inspiration from Kill Bill Vol. 1 and Vol. 2, and there will be plenty of cocktails included to round out the $80 meal.