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Date Ideas in Chicago
20s / 40s / Artsy / ATM / Average Joes
Party Earth Review A strange planet where tiki life meets retro drinking den, The Orbit Room attracts artsy hipsters and blue-collar locals alike looking for updated American pub fare paired with specialty drinks. Mature college students entering the single room lounge head to the leather-padded bar to sip one of the few craft beers on hand ... more
2959 North California Avenue
Chicago, IL 60618
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Ambient / Casual / Chill / Crowded
Reviewed by Joshua M.
"As a fan of anything related to the 1920's and The Great Gatsby, I was recommended this speakeasy-style bar from several friends and potential bootleg ..." more
3201 West Armitage Avenue
Chicago, IL 60647
30s / 40s / Ambient / Blouses / Dinner
Party Earth Review Inspired by a couple's trip to a wine bar in Spain – and their lassitude about remaining in the litigation world – Webster's Wine Bar is an unpretentious little venue that bottles up a whole world of wine. Whether to vie for the budget-friendly flights, the featured wine, the informative classes, or just to lay waste to ... more
1480 West Webster Avenue
Chicago, IL 60614
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20s / 30s / 40s / After Work / Ambient
Party Earth Review An offshoot of the adjoining Dunlay’s on Clark restaurant, D.O.C. Wine Bar is an oasis of civilized consumption in a neighborhood better known for its party-hardy post-college crowd. The lounge is almost cocoon-like, featuring a few porthole windows looking out onto noisy Clark Street and a starkly decorated industrial ... more
2602 North Clark Street
Chicago, IL 60614
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30s / 40s / Affluent / After Work
Party Earth Review Far removed from the bigger nightlife areas of Chicago, Arami entices discerning diners with Japanese fare way (WAY!) beyond California rolls. A Shinto gate marks the otherwise nondescript entrance, leading patrons into a small, modern lounge with exposed brick, a handful of candlelit bamboo tables, and a long sushi bar ... more
1829 West Chicago Avenue
Chicago, IL 60622
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30s / 40s / Ambient / Bar / Blouses
Party Earth Review Camouflaged behind a colorful plank façade adorned with an ever-changing display of graffiti art, The Violet Hour offers an unexpected touch of upscale luxury to a neighborhood better known for dive bars and hipster hangouts. A series of dark blue floor-to-ceiling curtains part to reveal the various rooms of the venue ... more
1520 North Damen Avenue
Chicago, IL 60622
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Acoustic / ATM / Balcony / Bar Food
Party Earth Review Substantially renovated in 2011 by Spike TV’s Bar Rescue, The Abbey Pub & Grill is an Irish pub-meets-concert hall that welcomes patrons with Guinness, guitars, shepherd’s pie, and a good dollop of soccer. Known as The Green Room, the pub/restaurant space sees couples cozying in around candlelit tables with bangers and ... more
3420 West Grace Street
Chicago, IL 60618
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20s / 30s / 40s / ATM / After Work / Bar
Party Earth Review Were it not for the large sign emblazoned across the stone façade and the two raised outdoor decks overflowing with boisterous patrons when the weather permits, The Galway Arms could easily be mistaken for a classy old house. Inside, this massive bar and restaurant opens into a collection of mini partitioned rooms, all ... more
2442 North Clark Street
Chicago, IL 60614
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20s / Artsy Dresses / Blouses / TVs
Party Earth Review Helmed by a former bartender from The Violet Hour and a GM whose previous ventures include The Aviary, The Barrelhouse Flat is a temple to craft cocktails located in an area better known for rowdy packs of college kids. The first floor has a saloon feel, with weathered exposed brick and a vintage jukebox that plays this ... more
2624 North Lincoln Avenue
Chicago, IL 60614
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20s / 30s / After Work / Bar Food
Reviewed by Carissa L.
"It’s not the most Irish of Irish pubs (RIP Johnny O’Hagan’s), but I always enjoy the food here. They have a delicious chicken, pear and goat cheese sa ..." more
3443 North Southport Avenue
Chicago, IL 60657
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Chicago Date Ideas Overview
Planning a date in Chicago? Well, it’s almost not fair how easy it is. In a city teeming with classy cocktail lounges, music venues, comedy clubs, and world-class restaurants, it is nearly impossible to go wrong.
Those hoping for a romantic date should head to the Signature Lounge on the 95th floor of the John Hancock Building, where they can sip cocktails and enjoy sweeping views of the city skyline. Afterwards, enjoy an exquisite meal at one of Chicago’s world-famous restaurants, such as Aviary or Girl & the Goat, which offers a fantastic foodie experience for those who love to eat.
Looking for something more casual? Chicago blues clubs offer a laid-back experience and unbeatable music on most nights of the week. Check out B.L.U.E.S. in Lincoln Park or Buddy Guy’s Legends in the South Loop for a relaxed date experience that is sure not to miss. Chicago is also home to hundreds of music venues across a variety of genres, so hipsters can take their sweethearts to Metro while metalheads enjoy date-night at The Mutiny.
Hipsters and cocktail-lovers should head to The Violet Hour for a romantic date. Or if the line is too long, try The Whistler, which also serves up classy cocktails and offers live music or DJs nearly every night of the week. Beer nerds can bring their dates to The Map Room, while whiskey-lovers should head to Fountainhead for an extensive scotch list and mouthwatering mac & cheese.
And of course, for those at a complete loss, it’s impossible to go wrong with a Second City show. A late night of laughs at this Chicago institution is sure to earn anyone a good night kiss.
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