Chicago Singles Overview

McFadden's Restaurant and Saloon - Irish Pub | Irish Restaurant | Sports Bar in Chicago

Single in Chicago? Plenty of people are! With such a young population, it is no surprise that Chicago offers plenty of upscale, laid-back, swanky, and divey spots where singles can meet, mingle, and more.

A great place to start is Hubbard Street, which offers a great variety of upscale and dress-casual watering holes and clubs where young singles sip martinis and flirt away. From Bull & Bear, a swanky sports bar full of well-dressed young professionals, to RockIt Bar & Grill, where energetic singles belt 80s ballads, Hubbard Street is generally a good bet for those looking to meet someone new.

Hipsters may choose a different route and bar crawl in Chicago’s most skinny jean-clad neighborhood, Wicker Park. With dozens of bars and clubs within a stone's throw of the Damen Avenue blue line stop, there are plenty of places to meet new people. The Flat Iron bar is a popular spot among Wicker Park locals, where Chicago singles can gather and flirt, all while downing whiskey shots.

Although it can be great fun to be single in Chicago, there are a few places to avoid. The Rush & Division corridor is known for older men trying to pick up younger women, and with the nickname “The Viagra Triangle,” it’s best to avoid this area as a single lady.

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