61. The Cubby Bear
City: Chicago, IL
Category: Nightlife
Telephone: (773) 327-1662
Address: 1059 W. Addison St.
Description: You don’t have to be a Chicago Cubs groupie to have a good time at this old favorite across from Wrigley Field, but it doesn’t hurt. On game days, expect some craziness, drunken debauchery, and potentially a wait to get in. Don’t expect fancy drinks (or even glasses) or upscale food. Do expect to give in to the fun. There’s also a lively lineup of live music acts, many of them cover bands like Rock Candy and Sixteen Candles, and popular live salsa on Sunday. Winter hours: Mon through Thurs for dinner and late night; Fri through Sun for lunch through late night; summer hours: non-game days open daily lunch through late night; game days open earlier (10 a.m., and on Sat at 9 a.m.).
62. The Fifty/50
City: Chicago, IL
Category: Nightlife
Telephone: (773) 489-5050
Address: 2047 W. Division St.
Insider Pick:
Description: Having met as managers at Joe’s Seafood, Prime Steak, and Stone Crab in Chicago, Fifty/50 co-owners Greg Mohr and Scott Weiner scored big with their own sporty, friendly, three-level Ukrainian Village bar and restaurant. Top menu options include their “triple secret” Heaven Burger with double-cream brie, pears, and smoked-berry jam; raved-about mac and cheese; wings with smoked-in-house and aged sauce; and sweet potato fries. Of course, there’s a hefty drink menu too. Beer cocktail, perhaps? Open daily for lunch and dinner, and Saturday and Sunday brunch.
City: Chicago, IL
Category: Nightlife
Address: 345 W. Armitage Ave.
City: Chicago, IL
Category: Nightlife
Address: 600 E. Grand Ave.
City: Chicago, IL
Category: Nightlife
Address: 3655 N. Sheffield Ave.
City: Chicago, IL
Category: Nightlife
Address: 9 W. Hubbard St.
67. Timothy O’toole’s Pub
City: Chicago, IL
Category: Nightlife
Telephone: (312) 642-0700
Address: 622 N. Fairbanks Ct.
Description: Combine the trappings of an Irish pub—a Guinness “black list,” for example—with a sports bar—tons of TVs (we’re talking 60-plus)—and you get this rowdy Streeterville spot. There’s also a full menu of burgers, ribs, chicken sandwiches, baskets of finger-licking fried apps, and award-winning wings (tip: of the seven sauces, the extra spicy clinched it). The Sunday brunch features a $20 bottomless Bloody Mary bar and $16 bottomless Mimosa bar. Any team jersey will get you in the spirit, but be forewarned that this is Bears football land. Open from 11 a.m. Mon through Fri and from 9 a.m. Sat and Sun.
68. Westend Bar & Grill
City: Chicago, IL
Category: Nightlife
Telephone: (312) 981-7100
Address: 1326 W. Madison St.
Description: Over near the United Center, there aren’t as many downtown drinking spots, but the founders of Four Corners Tavern Group opened this one a few years ago. Though some complain of too-loud music, it gets points for friendly service; plenty of space at the U-shaped bar and leather booths; a creative menu that includes surprises like chopped smoked turkey wraps, barbecue chicken nachos, and bacon cheddar pizza (along with standards and a kids’ menu too); and its free shuttle to Chicago Blackhawks and Bulls games. It fills up fast with pre-game drinkers, so get there early or right before the game starts when ticketholders file out. Open Mon through Fri from 5 p.m. (4 p.m. on game days), Sat and Sun 11 a.m. (9 a.m. on game days).
City: Chicago, IL
Category: Nightlife
Address: 3343 N. Clark St.
70. Celtic Crossings
City: Chicago, IL
Category: Nightlife
Telephone: (312) 337-1005
Address: 751 N. Clark St.
Insider Pick:
Description: Though it gave in and added a few TVs recently, this Irish pub in River North is still one of the most charming, conversation-friendly in town. You can’t miss the rich red exterior; follow it in and you’ll be warmly welcomed by its traditional old-fashioned bar, wood-burning fireplace, live music most nights—including Irish sessions on Sunday—and a perfect Guinness pour. Irish coffees come with hand-whipped cream, and Thursday features $5 Irish Car Bombs. Open Mon through Fri from 3 p.m., Sat and Sun from noon.
City: Chicago, IL
Category: Nightlife
Address: 444 N. LaSalle Blvd.
City: Chicago, IL
Category: Nightlife
Address: 100 W. Grand Ave.
City: Chicago, IL
Category: Nightlife
Address: 1300 W. Addison St.
City: Chicago, IL
Category: Nightlife
Address: 661 N. Clark St.
City: Chicago, IL
Category: Nightlife
Address: 1106 W. Lawrence Ave.