Somehow, Bar DeVille manages to be laid-back and quirky yet sexy, much like its patrons, who run the gamut from industry folks to creative types and hipsters. The dim lighting, extensive cocktail menu and craft beer list, old-school corner bar vibe, and French boudoir decor make it the perfect spot for meeting interesting, creative types.
While ESTATE definitely attracts a good-looking crowd, the vibe at this particular rooftop bar is slightly more chill and approachable than its Downtown counterparts. Not only does the jaw dropping skyline view at this riverfront spot provide a sultry ambiance, the StarDeck’s open layout and lounge seating make it easier to mingle and work the room... err, rooftop.
The color red is said to be both stimulating and able to evoke feelings of passion. While we’re not entirely sure if that’s true, we’ll be the first to admit that Slippery Slope’s red-lit bar does a pretty good job of setting a flirtatious mood. Keep things lighthearted and challenge your fellow singles to a game of Skee-Ball, or cozy up in a (stimulating?) red booth.
Near North Side
With its classy old-school interior and its status as one of Chicago’s best whiskey bars, The Berkshire Room is the perfect place to meet the Don Draper or Joan Holloway of your dreams. You know... if Don worked at a digital ad agency in River North and Joan lived in Lakeview. Anyway, what we’re trying to say is that The Berkshire Room is the perfect place to mingle with singles that fall into the “grown and sexy” category.
River North, Lakeview
Headquarters Beercade is the cure for anyone who’s found themselves pining for the dating scene they enjoyed in their youth. Plus, let’s face it: challenging an attractive guy/girl to an intense game of NBA Jam is much, much easier than trying to come up with a new and creative way to say, “So... do you come here often?”... and probably slightly more effective.
Thanks to its laid-back vibe, Rockit is one of the better (and least-intimidating) River North spots for singles. While the second floor lounge gets quite busy on Friday and Saturday nights, the weekday after-work crowd is comprised mainly of young professionals, making it less of a traditional singles scene and a bit more conducive to meeting right one rather than just the right booty.
Thanks to their '80s/'90s dance parties on Friday and Saturday nights, Innjoy is the perfect place to find a mate that shares your undying love for “Come on Eileen”. When the upstairs inevitably gets packed, grab your drinks and head to the basement for a more low-key rec room-style atmosphere that’s better suited to chatting.
Punch House’s laid-back rec room-themed atmosphere is quite conducive to mingling, and their signature bowls of punch are the perfect type of liquid courage you need to seal the deal. Of course, if that doesn’t work, you can always sneak into your preferred gender’s bathroom and write your name and number on the chalkboard walls... but just don’t blame us if some Tommy Tutone-wannabe turns your contact info into a song.
OK, so Nick’s Beer Garden may be a bad decision bar around the 4am mark. However, before 2am, the crowd tends to be friendly, laid-back, and very approachable, making it a good place to meet other singles. Of course, the cheap drink specials and nice outdoor patio don’t hurt, either. Just be sure to high-tail it outta there around 1:30am or so -- right around the time other bars in the area start announcing last call. Don’t say we didn’t warn you.
While WestEnd Bar may not be the best spot to meet ladies, the exact opposite is true for down-to-earth women on the prowl. Because it’s a popular spot to watch Chicago sports, the crowd skews towards males in their late 20s and 30s, yet is blessedly devoid of rambunctious frat boys. Of course, the fact that they make a killer Bloody Mary doesn’t hurt, either.
The combination of sunshine, sand, amazing lake views, South Beach-style cabanas, and tropical cocktails tends to attract a younger, attractive, and very, very single crowd to this North Ave beach venue. While you may not find your future husband or wife at Castaways, you can definitely find your next summer romance.
1. Bar DeVille701 N Damen Ave, Chicago
2. ESTATE Ultra Bar1177 N Elston Ave, Chicago
3. Slippery Slope2357 N Milwaukee Ave, Chicago
4. The Berkshire Room15 E Ohio St, Chicago
5. Headquarters Beercade213 W Institute Pl, Chicago
6. Rockit Bar & Grill22 W Hubbard St, Chicago
7. Innjoy2051 W Division St, Chicago
8. Punch House1227 W 18th St, Chicago
9. Nick's Beer Garden1516 N Milwaukee Ave, Chicago
10. WestEnd1326 W Madison St, Chicago
11. Castaways Bar & Grill1603 N Lake Shore Dr, Chicago
Craft drafts, liquor-forward libations, and hip environs -- such are the makings of a great night out at Bar DeVille. Manned by veteran bartender Brad Bolt and Chicago hospitality gurus Matt Eisler and Kevin Heisner, Bar DeVille offers expertly mixed cocktails, whether familiar classics or original favorites like The Hard Sell, made with Beefeater gin, Malort, St. Germain, and lemon. Come for the drinks, stay for the ambience: from the live DJ, pool room, and photo booth, to the Art Deco-inspired bar and refurbished Victorian sofas, this trendy neighborhood watering hole is frequented by industry folk and locals alike.
Claiming to be Chicago’s biggest al fresco rooftop, ESTATE Ultra Bar is the ideal Noble Square destination for those looking to sip with a scenic view and trendy ambience. While food is available in the way of New American light fare, the focus here is on the drinks, as the bar slings cocktails with “skinny” variations for the health-conscious and craft brews for the bros who throw down. If you’re unwilling to peel your eyes from the sweeping views of the Chicago River, there’s bottle service to boot.
Skee-ball, tamales, and and an expansive, crimson-lit dance floor await at this two-story club made to replace what Bonny's once was. The beer is cheap, the wine is boxed, and we promise this will probably be one of the only times you'll hear "Mother-In-Law" (a tamale-chili combo) and not be filled with dread.
Inside the Acme Hotel in River North, The Berkshire Room is an old-time cocktail lounge that harks back to when the hotel was called The Berkshire Hotel from the 1920s to 1950s. The drink selection puts a heavy emphasis on barrel-aged cocktails, but the real stunner is the Dealer's Choice, essentially an off-menu cocktail based on your choice of spirit, flavor profile, and glassware. The space is dark and cozy with black-and-white tiled floors and a long, glossy bar.
Cheers to never growing up. Headquarters Beercade lets you relive your childhood with all of the video games you loved and the added bonus of being able to consume alcohol while you play. There’s an extensive list of American craft drafts and games galore: whether you’re a pinball wizard looking for your next conquest, or brushing up your skills at arcade classics like NBA Jam and Mortal Combat, this bar is a gamer’s paradise. The space itself is sprawling and the vibe is convivial, making it a popular weekend destination for groups.
Rockit serves American-style cuisine with an upscale twist with bites like prosciutto parmesan garlic bread, bourbon chipotle maple wings, and buffalo calamari cobb salad. We recommend the burger with brie for extra gooey wonderfulness. Be on the lookout for their special menus, including a game day menu (so you can eat your feelings). It can get crowded during the weekends, but the after-work scene is much more laid-back and relaxed, making it the perfect place to catch up.
Innjoy in West Town is the perfect bar to head to when you really just want to dance your heart out to your favorite '80s or '90s song (Friday and Saturdays are the best night for this). Upstairs is where all the dancing occurs, but if you want to take your drink downstairs to the rec room-style basement, you'll have much easier time talking to a friend or date. In the summer, there is also an inviting patio to chill out when you need some fresh air after all of that dancing.
Located underneath Thalia Hall, Punch House is Pilsen’s underground, 70s-inspired basement pub specializing in… well, punch. With eight options on draft -- including classics like Milk Punch and Pisco Punch, and contemporary concoctions -- you can enjoy any one of them in a single-serving glass, in sno-cone form, in a carafe, or in a large-format bowl for groups. While punch is the real draw, they have an abbreviated list of craft cocktails, and a more extensive list of beer and wine for those less punch-inclined.
Nick's is a neighborhood bar that transforms into a packed madhouse in the early hours of the morning. Get there early to snag a table on their little back patio or, as they call it, the beer garden. To avoid the madness, arrive (and leave) before the 1:30am mark to enjoy the more laid-back and friendly crowd. They often have insanely cheap drink deals, which help the conversation if you're headed to this popular late night spot to meet someone new (if you know what we mean.)
WestEnd Bar in West Loop is the perfect place in Chicago to watch sports and down a few beers. The crowd is mostly men in their 20s and 30s, but it is (thankfully) free from the obnoxious bro type. The bar has half-price draft beers, wine and mixed drinks almost every day of the week. If you come to watch a sports game in the earlier hours of the day, order the killer Bloody Mary that will help cure anything left over from last night.
Located at North Avenue Beach, this bar and grill serves american classics (think burgers and sandwiches) along with a full menu of island worthy umbrella drinks, from daiquiris to margaritas. In addition to incredible lake views, this bar-on-a-boat has South-Beach style cabanas you can rent out to privately sip your very tropical drinks. Of course, this place is a hot spot during the summer, so come early to grab a good spot to take in the sun and sand.