Located on the north side of Chicago, the neighborhoods of Uptown & Edgewater contain some of the city's best hidden gems. From jazz clubs and beaches to gay bars adjacent to weekend brunch spots, these neighborhood make for a relaxing day among the LGBTQ-friendly locals.
It is apt that the gay beach in Chicago, popularly called Hollywood Beach, is officially named after Kathy Osterman, the Chicago politician who fought for gay rights in the 1980s. The beach is full of sandy stretches that, on a sunny Midwest day, makes you feel as if you are in Florida rather than Illinois. You’ll also find a friendly, down-to-earth crowd with a lot less attitude than other Chicago area beaches.
Chicago is known nationwide for its iconic storefront theatre scene–it’s the kind of theatre where you’ll experience knock-your-socks off acting and innovative, jaw-dropping productions from intimate 50-100 seat theaters. With over fifteen theater companies based in Edgewater, the neighborhood is a hotbed for the kind of theatre that’s put Chicago on the map and helped make Edgewater the vibrant, exciting community that it is. Our favorites include The Raven Theater on Clark Street, the Rivendell and Steep Theatre companies, and the NeoFuturists on Ashland Avenue
Not to be confused with Chicago’s famous Gino’s East pizzeria known for their deep dish pizza, this Edgewater gem is a family-run neighborhood institution that does cracker-thin pizza right. Best described as a “time warp”, this old-school joint is located underneath the Granville Red Line L stop and boasts a delightfully retro decor, complete with horseshoe-shaped leather booths and a curvy, back-light bar. Added bonus? Owner Peggy, who turns 86 this August, hand-makes the pies and the bartenders here are known for their filled-to-the-brim $5 pours.
A favorite in the community, this colorful and cozy Uptown spot known for its fresh and organic breakfast options and the charming, eccentric, décor. The menu here consists of creative Benedicts, breakfast burritos, corn arepas, and has a plethora of veggie and gluten-free friendly options. Insider tip: It is cash only and if you’re looking to “drunch” definitely opt for the Bloody Mary (hello garnishes!).
Big Chicks in Uptown, Tweet’s boozy sibling, has an amazing back patio, fun atmosphere, and well-priced drinks. If that’s not a winning combination we don’t know what is, which is why this place is a sure-fire favorite of locals. Don’t miss the free summer BBQ on Sundays and their oh-so-delicious vodka lemonades! This LGBTQ staple also features DJs and dancing after dark in the adjoining Tweet space.
Located half a block west from Gino’s North, this no-frills gay bar is worth popping into if only to marvel at the low set circular bar that sometimes doubles as—much to the bartender’s dismay—a catwalk for those looking to strut their stuff once a quarter’s dropped in the jukebox. While it’s a tad divey, the clientele here is as friendly and diverse as they come and the patio out back is a great place to kick back when the weather allows.
This retro cocktail lounge is one of the city's most famous music venues—and for good reason. Some of the best jazz and cabaret music takes the stage most nights, and on Saturday afternoons, an array of local (and, occasionally, famous acts) comedians, musicians, and storytellers perform at The Paper Machete, a free "live magazine" that embraces diverse, original voices.
by Amber Holst of Concierge Preferred
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