Chicago Gay Nightlife Guide: Andersonville & Uptown

Situated on the north side of Chicago - a mile or so north of the city's most gay-identified neighborhood, Lakeview - the diverse and engaging Andersonville neighborhood is also one of the top places to live, work, and play among LGBT persons. Historically home to large Swedish and subsequently Middle Eastern populations, the neighborhood began to gain popularity with lesbians and gays in the 1970s and has remained one of the city's alternative community hubs ever since. It's not just about the LGBT scene: Andersonville has few chain businesses and a strong appreciation for indie shops, cafes, bars, and restaurants. It's home to everything from feminists bookstores to one of the country's oldest gay bathhouses (see the Chicago Gay Bathhouse Guide for more on that). You'll find hipster eateries and one of the most successful branches of the gay burger restaurant and drinkery, Hamburger Mary's. 

Here's a look at a few of the best places in Andersonville for...MORE drinking, dining, cafe-going, and mingling with LGBT folks.

Another great neighborhood for exploring LGBT-friendly nightspots and restaurants is Lakeview, aka Boystown - have a look at our guide to that neighborhood. And for gay nightlife closer to downtown hotels as well as farther south, visit the Chicago Downtown Gay Bars Guide.

  • 01 of 05
    Hamburger Mary's, Chicago
    ••• Hamburger Mary's, Chicago. photo by Andrew Collins

    The popular gay burger franchise, Hamburger Mary's Brew & Grilles (5400 N. Clark St., 773-784-6969) is one of the more attractive ones in the chain, and it's also an easy-going, inclusive, and diverse hangout in the heart of Andersonville - a good spot for cocktails and to relax with friends on the patio, and a decent if not always consistently good place for a meal. This particular Hamburger Mary's also operates a craft nanobrewery that turns out some first-rate ales, including Mary Hoppins American Pale Ale and Leopold Belgian Dark Ale (plus lots of other rotating seasonal beers). As the name suggests, burgers (with campy names, like Queen Mary Burger and Big Kahuna) are the featured fare, but you can also get plenty of other pub-food items - veggie melts, Mandarin chicken salads, shepherd's pie, apple brown Betty, and a fun one called a GLBT sandwich (a blt with guacamole). Just down the street is Anteprima restaurant.

  • 02 of 05
    Big Chicks Chicago
    ••• Big Chicks, Chicago. photo by Andrew Collins

    Although not actually in either Lakeview or Andersonville, the endearingly fabulous gay bar Big Chicks (5024 N. Sheridan Rd., 773-728-5511) is relatively close to both district, in Chicago's ethnically diverse Uptown neighborhood. What stands out about this laid-back but highly popular gay bar with a vaguely sports-bar vibe is that it welcomes a genuine mix of lesbians, gay guys, heteros, and everybody else, and the crowd is age-varied and generally low on attitude but high on style. A very fun spot for cocktails, the bar adjoins the terrific restaurant, Tweet, which serves largely organic menu of good old-fashioned comfort foods - burgers (many veggie varieties available), sandwiches, salads, and the like. On Sundays, there's a barbecue-buffet cookout that's great fun.

  • 03 of 05
    Anteprima, Chicago
    ••• Anteprima, Chicago. photo by Andrew Collins

    Andersonville has a number of excellent restaurants but few that could be called bona fide destination dining experiences. Anteprima (5316 N. Clark St., 773-506-9990), however, is worth seeking out. This softly lighted, romantic purveyor of rustic but sophisticated Italian fare occupies a deep storefront space along Clark Street, and in warm weather there's additional dining on a wooden deck in back. Other notably gay-popular dining options in the neighborhood include Reza's and Hamburger Mary's, but this is definitely among the most serious food destinations in the area.

    Start off with a bowl of olives marinated in garlic, orange, and kicky chilies, along with fresh bread and a selection from the extensive collection of artisan olive oils. Other first-rate apps include cannellini beans with sopresetta and red onions, and veal meatballs with a saffron-tomato sauce, pine nuts, and raisins. A favorite pasta dish is the pappardelle with wild-boar ragu, or bucatini amatriciana...MORE (a vaunted shepherd's dish with pancetta, garlic, onions, tomatoes, and bucatini, which is a thicker version of spaghetti noodles). Crisp Cornish hen grilled "under a brick" with spicy rapini stars among the mains. Save room for pistachio-orange cake, or strawberries drizzled with balsamic syrup and topped with mascarpone and black pepper. For a romantic, memorable meal in Andersonville, Anteprima is hard to beat.

  • 04 of 05
    Jackhammer, Chicago
    ••• Jackhammer, Chicago. photo by Andrew Collins

    Rough, cruisy, and no-nonsense, the Jackhammer (6406 N. Clark St., 773-743-5772) lies at the northern reaches of Andersonville and hasn't succumbed to the trend in Lakeview of old-school leather-and-bear bars to gradually shift with the times and cater to a slicker, preppier bunch. Yes, this is your father's gay leather bar, presenting a particularly beefy cadre of male dancers on Saturday and Sunday nights. It's one of a handful of cruisy Andersonville gay nightspots, including Man's Country bathhouse.

    Continue to 5 of 5 below.
  • 05 of 05
    Reza's Chicago
    ••• Reza's Chicago. photo by Andrew Collins

    One of the many groups who have a significant presence in Andersonville are Arab-Americans and others of Middle Eastern heritage, and for this reason, the neighborhood has some very good restaurants specializing in food from this part of the world. One long-running favorite with the LGBT community is Reza's (5255 N. Clark St., 773-561-1898), which also has a branch downtown in River North (at 432 W. Ontario St.), and another in the town of Oak Brook (at 40 N. Tower Rd.). The rambling restaurant with large windows overlooking the street serves excellent food - specialties include tabbouli, vegetarian shami (sauteed patties of chickpea and green vegetable served with sweet-and-sour pomegranate sauce and crushed walnuts), and lamb Koubideh (skewered lamb kebobs with grilled tomatoes). It's on the same block at Women and Children First feminist bookstore, not far from Cheetah Gym.