20 Best Bars in Lakeview, Chicago

This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails. Two theaters host multiple shows seven days a week, and drinks and snacks are available for enjoyment during the performances. The Annoyance is mostly focused on improv and sketch comedy, but there are also burlesque performances, open-mic nights, and more. 

This North Side bar and music club brings in the crowds thanks to a good sound system and a great space for solid rock, alternative-rock, country, and rockabilly acts plus live local comedy during the week. On the Kitchen side, guests can order up salads, sandwiches, burgers, pizzas, and desserts. The well-earned popularity of the Belmont location spawned spots downtown on the Riverwalk and a Cantina location at Navy Pier.

This longtime country-and-western themed outpost still hosts line dancing two nights a week (with free lessons!) plus karaoke and bingo nights, and there's also a variety of queer acts throughout the week including all-male revues and multiple drag performances. 

This compact dive bar—one of the few that caters to lesbians, though it draws gay men, too—has an after-hours license, meaning the party's only getting started at 2am when when most other bars are at last call. Karaoke nights at The Closet are particularly energetic.

Diagonally across the street from Wrigley Field stands the Cubby Bear, a Chicago institution since 1953. It's the place where Cubs fans come to drown their sorrows in beer or lift one to celebrate. There are plenty of TVs for game watching, plus live music and a menu featuring burgers and other bar food.

When you combine an amazing whiskey list and tons of great craft beers with a dark, intimate space that plays great music like punk, rockabilly, alt-country and other outsider tunes, you get Delilah's. One of the coolest bars in Chicago for over three decades, Delilah's is a destination whether you want a rare pour of a hard-to-find bourbon, a game of pool, or just a cheap shot and a beer (because you can get one of each for just a few bucks every day).

Just up the street from Wrigley Field, Gman Tavern is a welcoming neighborhood tavern whose vibe is the opposite of the many rowdy sports bars nearby. The back room is outfitted with a small stage, a full bar, and a top-notch sound system for live music and comedy shows (it's also where a scene from The Color Of Money was filmed). In the front room, the well-stocked jukebox and well-curated beer list keep regulars and Cubs fans coming back.

This welcoming, female-owned tavern has been serving the city's craft beer scene since opening in 2011. The ever-rotating draft list focuses on local breweries from around Chicago like Spiteful Brewing and Half Acre, while also exposing patrons to more exotic beverages like the puckeringly sour Duchesse de Bourgogne from Belgium. A small array of wines and spirits supplement the drinks list, and patrons regularly pack the place for trivia nights and Euchre tournaments. 

One of the best-known queer night clubs in Chicago, Hydrate combines a relaxed front lounge with a late-night, high-energy dance floor in the back. Weekly events include DJs, drag shows, and viewing parties for RuPaul's Drag Race when the show is airing. Sundays see the post-brunch crowd stopping in for drinks and then dancing well into the night. 

This outpost of the Laugh Factory is part of the chain of comedy clubs that has locations in Hollywood and Las Vegas, among others. Shows like Chicago's Best Standup, The Nasty Show, and Latin XL take place throughout the week while national headliners also appear regularly. 

Nearly everyone who passes through Chicago plays at Metro at some point, from the best local bands to international superstars looking for an intimate club show experience (including bands like Metallica and Foo Fighters). It's among the best places in town to see live music, whether you're packed in on the main floor or above the fray in the balcony. In the basement is Smart Bar, a late-night dance club that starts hopping after midnight.

This unassuming joint claims the mantle of Wrigleyville's oldest bar, operating continuously since 1951. Whether it's thronged with Cubs fans on game days or by its loyal regulars in midwinter, the Nisei exudes a welcoming, divey vibe. If you want to sample Malört, Chicago's favorite unbelievably bitter liqueur best described as an acquired taste, no bar will be happier to introduce it to you.

Named for its location at the north edge of Boystown, this decades-old gay-friendly sports bar is a favorite spot for watching the game, shooting some pool, throwing some darts, or just having a cheap beer with friends. 

A neighborhood lounge that turns DJ-driven dance spot late at night, this newer entry on the Halsted Street strip makes a striking statement with its signature visual, a cloud-like illuminated ceiling sculpture that's visible from the street.

A longtime favorite, Roscoe's Tavern has a lot to offer its patrons, including a full all-day dining menu, jam-packed front bar, a dance floor, a pool table, an outdoor garden,  DJs on the weekends, and a sidewalk café in warmer weather. When it's airing, Roscoe's also hosts Drag Race aftershows that regularly feature former contestants. 

Built as a "tied house" in 1903 by the Schlitz Brewing Company (whose logo still adorns the exterior), Schubas Tavern favors local and national power pop, indie rock, and folk musicians. The laid-back, wood-paneled back room is the perfect place to hear artists who are just about to make it big. The attached and appropriately named restaurant, Tied House, serves creative comfort food.

With a shaded beer garden in summer and a roaring fireplace in winter, Sheffield's spans the seasons. The laid-back neighborhood pub with a craft beer and barbecue focus features more than 100 kinds of bottled beer, including an impressive list of vintage brews. You can also choose from up to 50 beers at one of the four bars, but for those not interested in brews, wine and cocktails are also available. 

In business for over 40 years, this sprawling, multi-level club packs them in by the hundreds each weekend thanks to the fairly priced drinks (and extremely rare cover charges). Events include show tune singalongs, glow stick dance parties, lesbian-friendly Sapphic Saturdays, and even events for dog owners. 

Of all the sports bars in Wrigleyville, Sluggers is perhaps the most famous. It's always packed before and after Cubs home games (and the ballplayers make occasional appearances in summer). Sluggers has a little bit of everything, including 40 TVs, fast- and slow-pitch batting cages, Skee-Ball, pool tables, air-hockey tables, electronic basketball, arcade games, and even a dueling-pianos show on the weekends. 

At the far north end of the Southport Corridor sits this humble neighborhood watering hole with a wide range of offerings that somehow all work well together. It's a Kansas City-supporting sports bar, with a menu offering New Orleans-style po'boy sandwiches, while also serving some of the city's best deep-fried buffalo wings. Toons also has an impressive beer list for a casual sports-focused environment, with 20 taps serving drafts from the likes of Dovetail, Three Floyds, and Haymarket. Need a budget beverage? Order a Chicago Handshake: a pint of Old Style paired with a shot of Malört.