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Date Ideas in Chicago
All Ages / Asian Food / Casual
Reviewed by Maria S.
"My Take: Deemed Chicago's First Sushi Restaurant, this Japanese sushi bar offers a variety of fresh options. If you are not interested in traditional ..." more
1531 North Wells Street
Chicago, IL 60610
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Absinthe / After Work / Blouses
Party Earth Review Right at home among the quaint brunch spots, casual ethnic restaurants, and quirky boutiques that call Andersonville home, In Fine Spirits is a cozy wine bar that exudes sophistication without exhausting patrons’ wallets. The space is bright and minimally decorated, with low lounge chairs and simple tables scattered down ... more
5420 North Clark Street
Chicago, IL 60640
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Button-downs / Cocktails / DJ / Bar
Reviewed by Scott N.
"One of the most underrated bars in Downtown Chicago. Instead of taking the usual route of most people. Try the skyline bar EPIC. Perfect for that s ..." more
112 West Hubbard Street
Chicago, IL 60654
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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30s / 40s / Business Types / Dinner
Party Earth Review Tantalizing plates of veggies, fish, and, yes, plenty of takes on goat give Girl & the Goat wide appeal among everyone from hardcore foodies to adventurous groups of trendy friends. Opened in 2010, Top Chef winner Stephanie Izard’s West Loop hotspot still sees reservations booked far in advance, but the cavernous loft ... more
809 West Randolph Street
Chicago, IL 60607
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30s / 40s / Alternative Rock / Bar
Party Earth Review The Midwest is miles from the salty ocean shores, so the hungriest sailors rely on Fish Bar, Lakeview’s interpretation of the New England crab shack. Sky blue exterior walls with a giant fish painted over the brick lure in many inquisitive seafoodies, while the ever-rotating selection of freshly caught grub keeps regulars ... more
2956 North Sheffield Avenue
Chicago, IL 60657
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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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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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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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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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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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