.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24

Queen Mary Tavern

The brains behind Pub Royale (No. 6) traveled just a few doors down to open this British-navy-themed bar. That means a lot of dark wood and plenty of hot tea punch in white porcelain kettles. But the real feat is that this spot somehow manages to feel both decades old and totally fresh all at … Read more

Bar Siena

From its opening night last July, the massive two-story follow-up to the River North restaurant Siena Tavern became the scene-iest of scenes for the trendy crowd making a night of it on Randolph Street. Stellar wine and beer lists: everything from the standard Lagunitas to the not-so-standard Ommegang Gnomegang blond ale. Bartenders mix ferocious cocktails, … Read more

The Heavy Feather

Skip the sweatfest at the Slippery Slope dance hall in favor of its second-floor sibling. The latest project from the team behind Scofflaw (Chicago’s top bar in 2013), the Heavy Feather has a ’70s fern-bar feel. The drinks are refreshingly retro (gin fizz, anyone?) yet still totally 21st century (the amaretto sour includes a healthy … Read more

Corridor Brewery & Provisions

This come-as-you-are sister to the stalwart Lake View brewery DryHop is a breath of fresh air on an increasingly yoga-pantsy stretch of Southport. Its six flavorful drafts steer clear of becoming total hoppy blowouts. Try to vulture a stool (seating is limited) and settle in at the nabe’s comfiest spot. 3446 N. Southport Ave., 773-270-4272 … Read more

Tack Room

If you can, snag a perch around the piano at Thalia Hall’s Western-themed space: It’s the best seat in the (very intimate) house. Between sips of the simple, easy-drinking cocktails (mostly classics, such as the Aviation or gin rickey, but a few impressive original creations, too), you can loudly sing along with the rotating cast … Read more

The Betty

Sick of complicated cocktails? Each drink on the menu, crafted by Peter Vestinos (Winchester), maxes out at four ingredients. Lots of terrific Eurocentric wines and craft beer options to enjoy in the vintagey space, too. Build in the wait time (about an hour at worst) to your trip. 839 W. Fulton Market, 312-733-2222 Crowd Google … Read more

Appellation

This casual spot next to the cheese shop Pastoral is filled with North Siders catching up over plates of charcuterie. Friendly servers will guide you through the 21 wines available by the glass, which include some excellent European and West Coast vintages. 5212 N. Clark St., 773-358-7181 Crowd Relaxed and all ages Food Cheeses, meats, … Read more

Flower Shop

Hit this companion to divey diner reboot Johnny’s Grill if you’re looking for a quiet place to get a simple, affordable beer or glass of wine. In this neighborhood, that’s increasingly rare. 3149 W. Logan Blvd., 773-278-2215 Crowd Dressed-down clusters of friends Food Diner eats from Johnny’s Top Tipple Moody Tongue nectarine IPA, $6

Sparrow

Salvation is at hand for those sick of fighting the sloppy, slurring masses on Division Street. No meat market here‚ just rum and hotel-lobby-themed poshness. 12 W. Elm St., 312-725-0732 Crowd Couples in heels and ties out for a nightcap Food None Top Tipple La Floridita No. 3 (white rum, maraschino cherry, lime, grapefruit), $12

Presidio

Welcome to the most romantic new lounge in the city. Whether you’re on your first date or 50th, you’ll appreciate the mood lighting, velvet upholstery, and mellow cocktails. 1749 N. Damen Ave., 773-697-3315 Crowd J.Crew-clad couples Food Full dinner menu Top Tipple Sweater Weather (sherry, Scotch, spiced chamomile cider syrup, lemon, dried apple, grated cinnamon), … Read more