Get Looped

It happens all the time: You’re downtown following a late night at the office or an evening show at the Goodman, and you want a drink. In a bad way. But  finding a decent cocktail (and a decent crowd) in the Loop can be as tough as nabbing a seat on the Red Line at rush hour. Thankfully, there are several places where you can settle in and hang out downtown—if you know where to look.

A striking dash of glam in contrast to the typical Loop bar’s grit, the WB draws a bevy of attractive locals to linger in its intimate cave of cool.
Dive factor (10 being the most divey) 0
Eat it Flash-fried calamari with arugula, grilled lemons and caper sugo ($11)
Best deal $8 mixed drinks. That may seem steep for a whiskey and coke, but it’s reasonable considering the drinks are made with 1.5-ounce shots rather than the standard 1 ounce.
Night owl score (10 being open the latest) 9
Mon–Fri 4pm–2am; Sat, Sun 5pm–2am. 172 W Adams St, 312-782-4933, midnightoilbars.com.

Upstairs, an affordable diner is stocked with a full bar and a menu of munchies. But take the stairwell or the elevator to the lower-level bar—or, better yet, the elevator to the roof deck with a gorgeous view of the skyline—and the Plymouth could easily become your crew’s new favorite hang.
Dive factor 6 in the diner, 5 in the bar, 1 on the roof deck
Eat it Grilled cheese and ham sandwich ($5.95)
Best deal $3 you-call-it well drinks on Thursdays
Night owl score 5
Mon–Sat 6am–11pm; Sun 7am–4pm.327 S Plymouth Ct, 312-362-1212.

The grimy view from Cal’s sidewalk chairs is as bleak as the inside of this tiny dive favorite—but that’s part of the charm. The El rumbles overhead, barely drowning out sloppy local bands, while bike messengers join career drunks throwing back $2 cans of brew.
Dive factor 10
Eat it A bag of chips from next door, you yuppie asshole.
Best deal A can of good ol’ PBR is $2, every night.
Night owl score 4
Sun–Thu 7am–7pm; Fri 7am–2am; Sat 7am–3am.400 S Wells St, 312-922-6392, drinkatcalsbar.com.

The Big Downtown Bar & Restaurant

Despite its unfortunate name and even more unfortunate logo, the Big Downtown is nice—posh, even. The waiters here sport white shirts, black pants and friendly ’tudes, and there are a handful of decent wines (although they ain’t cheap—a glass of Guenoc Cabernet Sauvignon costs $12).
Dive factor 4
Eat it Crab back appetizers ($14)
Best deal Inexplicably, they don’t offer drink specials, but a 22-ounce Leinenkugel Honey Weiss goes for $6.75 any day.
Night owl score 6
Daily, 6:30am–12am.124 S Wabash Ave (in the Palmer House Hilton), 312-917-7399.

Though it’s a chain, this English pub “concept” works when all you really want is a beer poured by a bartender who’s not going to give you attitude.
Dive factor 3
Eat it The Alaskan halibut fish and chips ($13)
Best deal A “British Imperial Pint” (20oz) of Guinness for $6, any night. No, that’s not a good deal, but it’s a good amount of beer.
Night owl score 5 Mon–Fri 6:30am–11:30pm; Sat, Sun 7am–11:30pm.111 W Adams St, 312-236-6656, elephantcastle.com.

Part of the Italian Village restaurant mashup, The Village offers a low-key but not scruffy place to grab a drink and some crispy thin-crust pizza. Take a left at the top of the stairs on the second floor and pull up to the bar, where the full Village restaurant menu is available, and the kitchen is open until 11:45pm on weekdays, 12:45am on weekends.
Dive factor 2
Eat it A half order of risotto primavera ($8.95), dotted with zucchini, peppers, peas and sun-dried tomatoes, makes a filling late-night meal.
Best deal $8 for a glass of earthy, peppery 2005 Cusumano Syrah
Night owl score 6 Mon–Thu 11am–midnight; Fri, Sat 11am–1am.
71 W Monroe St, 312-332-7005, italianvillage-chicago.com.

During the week, they’ll turn you politely away at the door after about 8:30pm, but if you’re around earlier (or on the weekend), poke your vodka-loving nose in the door at Russian Tea Time. The red awning and general poshness are intimidating, but the staff—and the prices—are plenty welcoming. The expansive vodka list features vodka flights—three 1oz. shots for $11. You can pick from the list, or make your own flight. We always choose from the ten house-infused vodkas, especially the bracing lime and the hurts-so-good horseradish, served ice cold. There’s a full dinner menu, but if drinking is the main goal, the hot appetizer menu offers plenty of sturdy dishes to cushion the blow to your system.
Dive factor 0
Eat it We can’t get enough of the blinchiki (blintzes filled with ground beef and carmelized onions, $9.95) or the vareniky (dumplings filled with potato, pumpkin, beef, or asparagus and cheese, $6.95).
Best deal If a vodka flight is a bit much, try a single two-ounce shot of any one vodka for $8.
Night owl score 2 Sun–Thu 11am–9pm; Fri, Sat 11am–midnight. 77 East Adams St, 312-360-0000, russianteatime.com.

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In the Loop: If you're having trouble picturing the various bars and restaurants in this article, check out this photo gallery of these fine - and not-so-fine - Loop establishments.