3329 N. Lincoln Ave. 773-281-7300
This local institution warmed up its ovens in the 1920s and still is charming locals with its doughnuts, which range from cinnamon-sugar to sour cream to old-fashioned glazed.
3159 N. Southport Ave. 773-525-2508+
The beautiful wood-accented back room of this hundred-year-old building is one of the city's best places to catch touring and local acts before they get big, while the front bar area serves up a mean mac 'n' cheese.
The Gingerman Tavern
3740 N. Clark St. 773-549-2050
Refreshingly unpretentious, this beat-up bar is the perfect place to escape from—or mentally prepare for—the insanity of Wrigleyville with a game of a pool.
2871 N. Lincoln Ave. 773-549-5549
A small club featuring mostly local and regional acts seven nights a week, this noted venue stood at the center of Chicago's emerging acid jazz movement in the '90s, helping to launch groups like Liquid Soul.
1300 W. Addison St. 773-477-2900
Behind the distinctive ivy-covered facade of this neighborhood institution, regulars can partake in board games and beers in one of Lakeview's coziest settings.
Music Box Theatre
3733 N. Southport Ave. 773-871-6604
This historic theater, which first opened in 1929, features an unbeatable lineup of independent and foreign films in addition to frequently hosting one-of-a-kind talks, film festivals and screenings.
Metro & Smart Bar
3730 N. Clark St. 773-549-4140
There may be no prouder accomplishment for a Chicago band than headlining at this legendary theater, which has hosted countless famous acts in its 30-plus-year history. Downstairs, DJ-fueled Smart Bar caters to the city's house and electronic scene.
1059 W. Addison St. 773-327-1662
With its location steps from Wrigley Field, this iconic bar is mostly known as a place for sports fans, but it regularly books local and touring acts, offering fans the chance to see major bands in a small room.
Vic Theatre/Brew & View
3145 N. Sheffield Ave. 773-929-6713
Alternately a music venue and a movie theater, this celebrated locale is the perfect place to catch prominent touring artists or enjoy a few beers during rowdy screenings of second-run and classic movies.
The Chicago Diner
3411 N. Halsted St. 773-935-6696
"Meat-free since '83" is the motto at this restaurant, which looks like a classic American diner but serves vegetarian and vegan versions of comfort foods such as reuben sandwiches, country-fried steak and even a turkey dinner on Thanksgiving. For a serious feast, order the Southern Style, a vegan platter of spicy buffalo wings, mac 'n' cheese, greens, black-eyed peas and jalapeno corn fritters.
Tac Quick Thai Kitchen
3930 N. Sheridan Road. 773-327-5253
This eatery is known for the authentic dishes on its "secret" Thai language menu, but the regular menu features plenty of pan-fried noodle dishes and curry bowls that can be made with tofu instead of meat.
3257 N. Halsted St. 773-248-6160
French-trained Japanese chef Yoshi Katsumura cooks seafood specials that change often based on what's fresh, but tried-and-true favorites such as roasted Cornish game hen and a wagyu beef burger piled high with toppings are always available.
909 W. Belmont Ave. 773-348-2378
This Swedish restaurant has earned a legendary reputation for its sticky sweet cinnamon rolls. The first Ann Sather opened in 1945 just a few storefronts down from this location, so this is arguably as close as you'll get to the original.
3325 N. Broadway 773-477-8533
"Big fun in a lil' gay bar" is the motto at this lesbian-owned Boystown fixture, which opened in 1978 and is about as small as you'd expect from the name. Thanks to a late-night license, it's open until 4 a.m. (5 a.m. on Saturdays) and grows most crowded after the rest of the neighborhood's bars and clubs close for the night.
954 W. Belmont Ave. 773-348-4975
Dark, loud and sweaty, this anything-goes melting pot of a dance club keeps the party going all week long with everything from theme parties to album release bashes to dollar drink night.
Clark Street Dog
3040 N. Clark St. 773-281-6690
Got a late-night hot dog craving? This local legend has been around since the '70s and is open until 3 a.m. nightly—and until 4 a.m. on weekends.