Chicago Gay Nightlife Guide: Lakeview & Boystown

One of the most visible gay district in America, Lakeview - known more familiarly by its nickname, Boystown - is a lively and richly historic Chicago neighborhood on the city's north side. It's been the center of LGBT life for decades and is where the heart of the city's Chicago Gay Pride parade and related festivals take place in June. 

Lakeview stretches from Lake Michigan's shoreline west for about 2 miles to Ravenswood Avenue, and extending north above Lincoln Park neighborhood (at Diversey Parkway) about 2 miles to Sheridan Park (at West Montrose Avenue). Much of the gay scene is focused along north-south-running Halsted Street as well as east-west-running Belmont and Addison streets. 

Lakeview East comprises the blocks of Chicago's Lakeview area nearest the lake and including such bustling commercial strips as North Broadway and North Halsted. You'll find dozens of gay- and lesbian-popular shops, restaurants, bars, and other businesses throughout the neighborhood, which is bound by Diversey Avenue, Halsted Street, Grace Street, and Lake Michigan (the epicenter is around West Belmont Avenue at North Broadway, which is another of the main commercial strips of Lakeview. Among the many gay-popular shops and eateries along this stretch, check out Unabridged Bookstore, Joy's Noodles, Coffee & Tea Exchange, and Wiggleyville

Here's a look at some of top gay bars and gay-popular restaurants in Lakeview and Boystown. The neighborhood is also home to the popular gay sauna, Steamworks - check out the Chicago Gay Bathhouse Guide for more information on this establishment.

Another great neighborhood for exploring LGBT-friendly nightspots and restaurants is Andersonville - check out our dining and nightlife guide to that neighborhood. And you'll also find some fun bars in other parts of town: check out the Downtown and Southside Chicago Gay Nightlife Guide for other areas.

Berlin - gay bar

Berlin nightclub, Chicago
photo by Andrew Collins

A friendly dance club along Boystown's busy Belmont Avenue, Berlin (954 Belmont Ave., 773-348-4975) has been a gay nightlife mainstay in Chicago for many years, its success due largely to its come-one-come-all vibe - on any given night you might see hot muscle twinks, baby dykes snogging on the dance floor, trans revelers, curious heteros, salt-and-pepper-haired yuppies, alt-goths - you name it. It's a fun place early or late, and you can always count on interestig, dance-worthy music. It's just around the corner from Halsted Street and the many gay bars along there - Minibar, Roscoe's, Sidetrack, etc.

Sidetrack - gay bar

Sidetrack bar, Chicago
photo by Andrew Collins

An immensely popular gay video bar in the heart of Chicago's Boystown neighborhood, Sidetrack (3349 N. Halsted St., 773-477-9189) is a rambling place comprising a few different bars on two different levels. This place stays busy early and late, and tends to appeal to a wide range of patrons - gay men and lesbians of all ages, though tending toward the professional, preppy side. It's really a prime fixture in the neighborhood, and for Chicago's LGBT community as a whole. Depending on the night, the video screens play show tunes, comedy, retro videos, or popular current music. And there are a number of monthly parties and special celebrations, too. This is one of the city's must-see gay hangouts for visitors, and it's along a busy block of gay nightlife that includes several other clubs and bars, including Hydrate and Roscoe's Tavern.

Progress bar - gay bar

Progress Bar Chicago
photo by Andrew Collins

A swanky nightspot with a fanciful, eye-catching "cloud" ceiling, Progress Bar (3359 N. Halsted St., 773-697-9268) draws a well-dressed bunch; it's in the space formerly known as Cocktail. The name is meant to evoke the idea that the LGBT has come a long way toward being inclusive and all-welcoming, and indeed, the crowd is fairly mixed, and the bar serves exceptional craft cocktails and boasts a nice selection of craft beers, from Dogfish Head 60 minute to Boulevard Tank 7. It's a good spot to meet up with friends at happy hour before dinner, or to wind down an evening. The staff is particularly friendly and nice, and the mood festive. It's one of the nicer gay lounges along Halsted, along with Roscoe's, Sidetrack, and Minibar.

The Closet - lesbian/gay bar

Among Lakeview gay bars, The Closet (3325 N. Broadway, 773-477-8533) has long cultivated a friendly, mixed-gender following - in fact, it's arguably the most lesbian-popular hangout in Lakeview (and also fairly popular with straights - basically, everybody is welcome here). It was opened in 1978 by two women (a big deal at the time!), and it's never stopped being an inviting and inclusive space. There's a little dance floor, and TVs show music videos and such most of the time. It's basically your friendly locals bar in Lakeview - an easy place to meet new souls. This is the only gay bar along North Broadway, and it's close to the Best Western Hawthorne Terrace and such restaurants as Joy's Noodles & Rice.

Lark - restaurant/mixed bar

The trendy and inviting neighborhood bistro Lark (3441 N. Halsted St., 773-799-8968) opened in summer 2016 in the space formerly occupied by the long-running gay-popular hangout Halsted's Bar + Grill. This rustic-chic space has the same owners as the previous establishment, and they've definitely kicked up the food and drinks offerings a notch and also have cultivated a strong following for the weekday happy hour period (5 to 7 pm), for brunch on weekends, and for late-night nibbling (the kitchen serves until late. The menu offers a forward take on American comfort classics - think parmesan pizza "bones' (wood-fired bread sticks), homemade beef-pork meatballs in a tomato-vodka sauce, and braised-pork Cubano sandwiches. It's simple fare, well-prepared, in a dapper space

Roscoe's - gay bar

Roscoe's Tavern, Chicago
photo by Andrew Collins

One of the great legends of gay Chicago nightlife, Roscoe's Tavern (3356 N. Halsted St., 773-281-3355) has remained fun, relevant, and busy since it opened in 1987, despite the presence of many newcomers along Halsted Street over the years. It's across the street from Progress and near plenty of other restaurants, bars, and shops in Boystown, including Lark and Sidetrack. One feature that makes Roscoe's a favorite for groups of friends is its nightly $15 "pitchers" specials - pitchers Absolut Mandarin Cointreau cosmos, Skyy Moscato sparklers, and Absolut pink lemonades are among the offerings, depending on the night.

Home Bistro - restaurant

Among the many gay-popular restaurants along Halsted Street and elsewhere in Lakeview (such as Chicago Diner, Lark, and Nookies Tree), Home Bistro (3404 N. Halsted St., 773-661-0299) stands out for its remarkably tasty, inventive, and well-priced contemporary American (with Mediterranean accents) cuisine - dishes like pan-roasted monkfish with littleneck clams and chickpea salad, double-cut pork chop with rhubarb jam, and almond-stuffed dates wrapped in bacon. There's also a quite popular Sunday bunch where you might sample Spanish chorizo hash or kalbi beef tacos with cabbage slaw and pickled jalapenos. The restaurant occupies a dapper storefront with a tan and brown interior and vintage mirrors on the wall. Good fun for a first date!

Chicago Diner - restaurant

Since 1983, the seemingly old-school Chicago Diner (3411 N. Halsted St., 773-935-6696) has been serving an entirely vegetarian menu, including some highly inventive fare that even meat-lovers rave about. Favorites include the apple-almond salad with mustard-balsamic dressing and dried cranberries; roasted-veggie lasagna with a pesto vegetable saute; and the gyros with sliced seitan, chopped onions, tomatoes, vegan tzatziki sauce, and Spanish rice. The chocolate-chip cheesecake earns plenty of kudos among the desserts. The casual spot with rustic wood floors, deep wooden booths, and a cheery patio out back lunch and dinner seven nights a week and has long been a friend to Chicago's gay and lesbian community. There's also a branch in hipster-favored Logan Square at 2333 N. Milwaukee Avenue.

Hydrate - gay bar

Occupying the site of the long-running (and infamously raucous) Manhole club, the somewhat more eclectic but still quite cruisy Hydrate (3458 N. Halsted St., 773-975-9244) dance club has earned a loyal following for its imaginative theme nights (such as Friday night's Beauties and Beaus, featuring some of the hottest strippers and campiest female impersonators in the city, and occasional lube-wrestling competitions). Mostly, though, it's just a pounding and pulsing place to dance to some of the best music in the neighborhood and check out hot and shirtless patrons. Plenty of the guys who hang out here also party at Sidetrack, and you may also see a few of these fellas at Steamworks Bathhouse later in the evening.

Kit Kat Lounge & Supper Club - mixed bar/restaurant

Kit Kat Lounge Chicago
photo by Andrew Collins

One of Lakeview's swankier mixed gay-straight lounges and eateries, Kit Kat Lounge & Supper Club (3700 N. Halsted St., 773-525-1111) is a swish, retro-hip hangout that's ideal for sipping fancy cocktails or for a full meal. The kitchen turns out commendably prepared international fare (Thai spring rolls with lobster and rock shrimp, wasabi shu-mai pork dumplings, pumpkin-seed-encrusted halibut with a spicy cilantro-cream sauce), and many of the glamorous staffers dress in drag. It's close the the LGBT Center on Halsted, and at the northern end of a strip of Halsted Street hangouts that include Scarlet, Cocktail, and Hydrate. Kit Kat also has the gay-popular Kit Kat Toronto.

Harmony Grill and Schubas - restaurant/live music club

Attached to the venerable live-music club Schubas, the Harmony Grill (3159 N. Southport Ave., 773-525-2508) is a lively, laid-back spot for delicious takes on American comfort food, including highly popular brunches - think Korean barbecue wings, incredibly rich mac-and-cheese, smoked-turkey cobb salads, and exceptionally good home-style grilled sirloin, and all at great prices. The chocolate-bread pudding dessert with Maker's Mark caramel sauce is impressive. For brunch, consider cheddar corn cakes with black beans and topped with eggs any style. The restaurant-bar is on the west side of Lakeview, a short walk from the Boystown action along Halsted Street (i.e., Roscoe's, Berlin, Sidetrack), and it doesn't have as gay a following as some. Or perhaps more to the point, the live-music venue at Schubas pulls in a wide range of folks from all over metro Chicago to see live blues, rock, and alternative music. The owners also operate the similarly esteemed music venue Lincoln Hall, in Lincoln Park.

Scarlet Bar - gay bar

For years the Gentry on Halsted (pictured here shortly before it closed), a Lakeview sister to the former Gentry gay bar downtown, entertained the suits crowd with piano cabaret and a relaxed, low-keyed atmosphere. Since taking over the Gentry place about a decade ago, gay-bar-hoppers have very much enjoyed Scarlet (3320 N. Halsted St., 773-348-1053), a cosmopolitan, upscale gay lounge and dance club known for its dandy drink specials and sleek decor. It's a relatively intimate space as Boystown dance clubs go, but that makes it all the more fun if you're wanting to get close to somebody you admire on the dance floor. Other low-attitude, fun hangouts in the neighborhood include Kit Kat Lounge and The Closet.

Nookies Tree - diner/restaurant

The silly-named Nookies Tree (3334 N. Halsted St., 773-248-9888) serves reliably good traditional American fare - burgers, eggs, steak-and-cheese sandwiches, French toast, and similarly hearty food that patrons especially appreciate late on weekend evenings after bar-hopping. Nookies is open 24 hours on Fridays and Saturdays, and until midnight the rest of the week.

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