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)
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)
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
BEER So you’ve mastered the art of pairing beer with fish, steak and maybe even Thai food. Bravo. Now you need to pick a brew that will work with eight courses of craziness at Schwa. The meal’s going to have ingredients you can’t even identify, let alone match up to beer. If there’s one style that can handle anything you throw at it, it’s saison. Known as a “farmhouse” ale due to its history as a Belgian-farmer brew concocted during harvest season, saisons are now being crafted stateside with delicious results. A saison’s carbonation can cut through fats or dance off a dish’s acidity, and its earthy malts, citrusy hops, and balance of spice and sweet almost seem to adjust according to what you’re eating. The Belgian Saison Dupont is a measuring stick for the style, while Ommegang Hennepin is a favorite American take. —Heather Shouse
WINE There’s no telling what you’re going to eat at a place with an ever-changing menu, so there’s no telling what wine you should bring. One thing is for certain, though: You’ll eat a lot of rich food. In this instance, sparkling wine is your best friend. People say sparkling goes with everything, but the truth is it doesn’t so much go with it as it scrubs flavors off your palate, prepping you for the next bite. It even cuts through butter and cream without effort, making it a perfect foil for heftier foods. So buy a bottle of Mionetto’s charming IL prosecco (the cheap, casual option), the M. Lawrence Sex (a sparkling rosé from Michigan) or go big (and pricey) with a bottle of one of the world’s most delicious creations, Laurent-Perrier Champagne. And whatever you do, drink it before it goes flat. —David Tamarkin