52 Best Bars in Lincoln Park and Wicker Park, with Bucktown and Logan Square, Chicago

Bungalow by Middlebrow wears a lot of hats---brewery, natural winemaker, sourdough bread bakery, pizzaiolo, all-day neighborhood third place---and looks darned good in all of them. There’s a relaxed, come-one-come-all feeling to the dining room and patio here; indie folk types play mellow sets while friends sip wild ales and families linger over pizza. Fun one-off events, like block parties and collaborative pop-up dinners, are frequent; check in with the house Instagram account ( instagram.com/middle_brow) to find out what's upcoming.

This place may have toys and knickknacks around the bar (including a case of macabre baby-doll heads), but when it comes to booking rock, punk, and jazz bands from the indie scene, it's a serious place with no pretensions. Grab some grub next door at Pizza Friendly Pizza before the show—the thick Sicilian-style squares, created in collaboration with fine dining vet Noah Sandoval, are among the best pizza bets in the whole city.

The Hideout, which is literally hidden away in a North Side industrial zone, has managed to make country music hip in Chicago. Players on the city's alternative country scene have adopted the friendly hole-in-the-wall, and legendary local acts like Wilco and Andrew Bird have been known to use the crowd here as a sounding board for new material. Late-night DJ sets, stand-up, and even the odd square dance round out the entertainment offerings.

In West Town near Wicker Park, the Matchbox isn't much bigger than a you-know-what, but the hodgepodge of regulars doesn't seem to mind. In fact, many claim it's the dark, cramped quarters (we're talking three feet wide at its narrowest) that keep them coming back. A heated front patio comes in handy when you need to reclaim a little personal space. You're practically required to try the signature drink, a margarita.

Just a stone's throw from Second City, Old Town Ale House has attracted a diverse cast of characters since it opened in 1958, including comedy legends John Belushi and Bill Murray. With eclectic artwork and a mural of bar denizens painted in the 70s, it's a dingy neighborhood bar unlike any other in the city—perhaps the country. Esteemed film critic Roger Ebert called it "the best bar in the world."

Lovers of vintage bar rooms will be in heaven at this veritable 1950s-era time capsule on Division Street. After shuttering in 1975, it was left undisturbed until 2015, when a local hospitality group dusted off the warm wooden interior and reopened the doors. Today there’s an emphasis on nautical quaffs like grog and navy strength gin. The Sunday and Monday oyster and martini happy hour is a favorite with locals.

On a given night at Rosa's Lounge, you'll find Tony, the owner, working the crowd. He moved here from Italy out of a pure love for the blues, and what makes his club special is a gritty authenticity that some of the sleeker city center blues establishments lack. Stop by and partake in Rosa's winning mixture of big-name and local talent, stiff drinks, and friendly service—the same since it opened in 1984. Take a rideshare after the show, as this corner of the neighborhood can be a bit rough around the edges at night.

The epicenter of comedy since 1959, The Second City has launched the careers of countless comedy legends, including Bill Murray, Catherine O’Hara, Stephen Colbert, Tina Fey, and Keegan-Michael Key. The revues on the company's historic Mainstage and more intimate e.t.c. space are fully realized sketch comedy shows, but the prescripted material is developed through improvisation in front of audiences. There’s always plenty of time in each show devoted to demonstrating the comedy chops of the quick-witted performers. Most nights, a free improv set after the late show features cast members and invited guests (sometimes famous, sometimes not). UP Comedy Club presents award-winning touring shows, comedy festivals, and special guest performances. In Donny's Skybox upstairs, you're likely to see one of Chicago's many fledgling improv comedy troupes debuting fresh material.

You know a taproom takes beer seriously when they specify exactly what temperature their drafts are served at. That's the Beer Temple, an inviting space with around 20 ever-changing handles and lots of seating for the requisite beard-and-flannel types. Do pay a visit to the fantastic bottle shop, which precedes the taproom by several years. It specializes in super-limited-release local drops and brews from Belgium and France, and the staff's knowledge of obscure brewers and beer styles is mind-boggling.

This Logan Square cocktail go-to with an impressive catalog of vintage spirits focuses on elevating classic drink recipes by using unexpected ingredients. The Charlie Trotter's alums who opened Billy Sunday cheekily named the bar for the Prohibition-era temperance evangelist.

This breezy, seasonal, casual bar and grill puts you so close to Lake Michigan that you might consider wearing a swimsuit. Perched atop the North Avenue Beach Boathouse, Castaways creates the perfect setup for lazy summertime sipping.

Chef’s Special brings fun energy to Bucktown’s bar scene with brightly flavored cocktails in colorful shabby-chic digs. Don’t snooze on the menu of kitschy classic Chinese-American dishes; the kitchen is overseen by the team from Giant, the Logan Square favorite. Happy hour, held every evening from 5pm to 6 pm, means the place is packed within minutes of opening. 

The old-school taverns tucked at random along Bucktown's residential streets---many distinguished by a vintage Old Style beer sign---are a major contributor to the neighborhood's character, and this one (the latest iteration of a series of bars that have existed on this site since the 1950s) is a prime example. Come for the ice-cold beer, the easygoing dive vibe, and the jukebox tunes.

In the historic Flat Iron Building, the Debonair Social Club combines visual arts, music, and late-night dining. Upstairs, curated video installations line the walls surrounding the stage-cum–dance floor; the dimly lighted downstairs has a more clandestine feel.

A rare dive bar amid Lincoln Park's tonier establishments, Delilah's is dark and a bit grungy. But the bar has a friendly, unpretentious vibe and a standout whiskey selection (more than 800 types are on offer). DJs spin punk, metal, and rockabilly.

Two of America’s favorite pastimes—drinking and playing classic arcade games—come together here. More is more is the governing M.O.: there are over three dozen arcade games to choose from, along with Skee-Ball, pinball machines, and around two-dozen beers on draft. There are also locations in Logan Square and the West Loop. 

Mexican spirits like mezcal, sotol, and raicilla are the focus at petite Estereo, which has an unusual triangular shape due to its position on an angled corner lot. When the garage-style windows that surround the room are rolled up and the vintage Latin tunes are pumping, you’d be forgiven for thinking you’d been transported to a city much nearer to the equator.

Although it's a 30-minute schlep west of downtown Chicago, FitzGerald's draws crowds from all over the city and suburbs with its mix of folk, jazz, blues, zydeco, and rock. This early 1900s roadhouse has both great sound and sight lines. There's a menu of fantastic barbecue fare from Babygold, the adjoining restaurant. During the family-friendly Sunday brunch, it's paired with live acts that run the gamut from classic country to New Orleans funk.  

Full of sports fans and former frat boys, Gamekeepers has more than 40 TVs, three projection screens, and complete satellite sports coverage. There's barely a game it doesn't get.

It's probably just our imaginations, but somehow the sunlight that streams over the vintage tiles and velvety banquettes in this easy-going Humboldt Park cocktail bar seems to glow. An equally dreamy side patio has a second bar and a brick fireplace flanked by lots of low seating for basking in the firelight once the sun sets. Dogs are very welcome here.

Formerly called ImprovOlympic, I.O. is the city's home for long-form improvisation. The signature piece is "The Harold," in which a team of improvisers explores a single audience suggestion throughout a series of stories and characters until they all eventually weave back together to fit with the original audience idea. There's no drink or age minimum. Seating is first-come, first-served, so be sure to arrive early, especially for weekend shows.

Popular Kincade's packs 'em in on two levels with a 10-foot-wide video monitor, several plasma screens, and a bar menu that invites patrons to linger for a game—or three. An outdoor beer garden, pool tables, and French doors that prop open on warm summer days are added bonuses.

In 1968, Kingston Mines went down in Chicago history as the first blues club to open on the North Side, and it's hosted luminaries like Koko Taylor and Junior Wells. Though it's since moved to bigger digs with not one, but two stages, it still offers the same traditional sounds and late-night hours as the original club. Have something you need to get off your chest? Work it out at the Sunday evening open blues jam.

Enjoy late-night music, potent martinis, and Gothy vibes? Late Bar, located along a somewhat lonely stretch of Belmont Avenue, is the place for you. The best time to come is Saturday night, when the club is bumping with New Wave classics until 5 am. 

Done up in pretty Prussian blue with warm walnut accents, this wine bar/bottle shop channels calm vibes—and if you're still feeling keyed up, a pour or two from the Eurocentric wine list should do the job. Standard wine bar fare like cheese and charcuterie plus a few Spanish-inspired pintxos make up the small food menu. 

The owners of Lincoln Hall transformed a former movie theater into an intimate concert space with great sight lines, an excellent sound system, and a wraparound balcony with seating. The booking is always on point, so it's worth taking a chance on a lesser-known band. A separate bar up front pours preshow pints from local breweries.