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Schwa
Like trying to reconnect with a former lover, getting a date at Schwa requires a fair number of humiliating unreturned voice mails. After clearing the reservation hurdle, the rest is easy: Order the nine-course menu, and chef Michael Carlson’s wacky creations—such as crispy sweetbreads for dessert—will have you licking the red-pepper paint off your plate. 1466 N Ashland Ave, 773-252-1466.
Corkage fee $2.50 per person
Best nearby liquor store Todd’s Wine (1616 N Damen Ave, 312-698-9952)
Café 103
If the terms BYOB and seasonal American cuisine don’t have you immediately thinking 103rd Street, this small, simple South Side spot is reason to reconsider. Winter comfort foods go slightly upscale in dishes like roasted cauliflower soup with bacon bits and a brined, mustard-glazed pork chop served with a turnip puree and grilled cabbage. 1909 W 103rd St, 773-238-5115.
Corkage fee $5 per bottle for wine, none for beer
Best nearby liquor store Town-Armanetti Liquors (10000 S Western Ave, 773-239-2800)
Urban Belly
There will be a wait, a crowded communal table and an awkward stool as a perch. But then there will be dumplings: tender wontons stuffed with brandy-spiked ground lamb or crisply fried pouches of fragrant duck meat. And finally, an enormous bowl of noodles—a spicy broth in which fried chicken and mango pieces mingle beautifully. 3053 N California Ave, 773-583-0500.
Corkage fee None
Best nearby liquor store Provenance Food and Wine (2528 N California Ave, #2, 773-384-0699)—Julia Kramer
The Kendall College Dining Room at 900 N. Branch Street also has BYOB and an amazing, affordable menu!!