Chicago’s Lakeview Neighborhood

Lakeview, aka “Boystown,” has strong cachet among gays and lesbians

A world-class city with one of North America’s most dynamic gay populations, Chicago is also a metropolis of lively, distinctive neighborhoods. Two of these areas, both of them on the city’s North Side, have especially strong cachet among gays and lesbians. Lakeview, aka “Boystown,” hugs the Lake Michigan shoreline and contains the wealth of the city’s gay bars and restaurants. Andersonville, about 3 miles northwest, is smaller but still has a great variety of bars and eateries popular with the LGBT set.

Although most of Chicago’s accommodations are downtown (15 to 20 minutes south by cab or a bit longer via public transportation), Lakeview does have a handful of reasonably priced, gay-friendly lodging options. If you’re planning a good chunk of your time in Lakeview (and Andersonville, which has no hotels but is relatively nearby), consider one of these properties, which generally have more reasonable rates (and much less expensive parking) than comparable hotels downtown.

These include the three properties that make up the Neighborhood Inns group, a collection of charming, intimate boutique hotels in the heart of Lakeview. City Suites sits along busy Belmont Avenue, closest to the dining and club action, while the more romantic Majestic and Willows hotels are set along peaceful residential streets a few blocks from the bars. The gay-friendly Best Western Hawthorne Terrace is a reasonably priced little gem right in the heart of Lakeview, a short walk from the beach on Lake Michigan. Personal service, free Wi-Fi, in-room refrigerators and microwaves, and pleasant furnishings make this 59-unit property a winner.

Lakeview is one of the city’s best neighborhoods for dining. Jack’s on Halsted mixes international ingredients and recipes to create such memorable treats as grilled lemongrass-crusted salmon, and day scallops with mushroom-parmesan risotto and white-truffle oil. Head to the Pie Hole Pizzeria for outstanding pies (try the Greek version, with spinach, gyro meat, tomatoes, red onions, black olives, and feta). In the western reaches of the neighborhood, stop by Harmony Grill for creative comfort food, including fantastic mac and cheese and decadent “blondie” sundaes – it’s attached to the happening music club, Schuba’s Tavern.

Matsuya serves excellent sushi and Japanese fare, including such knock-out starters as deep-fried chicken wings and whitefish with smelt roe. Although many imitators have opened nearby, Mia Francesca remains the best place in the neighborhood for sophisticated but simple Northern Italian fare. You could survive solely on the flaky, freshly baked cinnamon rolls that accompany every meal at the hallowed Swedish diner Ann Sather, which has several gay-popular locations.

Those seeking healthy food should head for the Chicago Diner, which specializes in creative vegan and vegetarian fare and serves delicious baked goods. An attractive little Thai restaurant where the rice and noodle dishes are delicious and cheap, Joy’s Noodles serves a terrific ginger chicken with a fragrant bean sauce. If you’re a java junkie, keep in mind that the cozy Lakeview outpost of the Caribou Coffee chain is known locally as “Cariboy” and “Queeribou” – that should tell you all you need to know about the crowd.

Boystown is the heart of the city’s gay-male nightlife scene. The yuppie bar Roscoe’s is practically a Chicago institution, fun for dancing and cruising any night of the week. A guy guzzling Bud longnecks and another sipping cosmos can feel right at home together at Cocktail, an intimate storefront bar where friends often meet up before heading out to larger clubs. Chicago’s classic stand-and-model video bar, SideTrack has plenty of rooms for mingling. Hydrate is one of the hippest gay bars in town, great for after-work cocktails or late-night dancing and cruising.

A swank, smoke-free lounge known for its colorful cocktails and slick crowd, Minibar opened somewhat recently and has become a favorite after-work spot. A circuit-boy favorite on weekends, Circuit pulses with a feverish late-night dance crowd even at midweek, when Latin nights are a hit. The stylish Berlin disco draws a decidedly funkier and more alternative crowd than most of the preppy haunts in Lakeview. Nearby Spin is an eclectic gay club with an all-ages crowd and fun dance music. Charlie’s brings in fans of country-western music, while the Gentry on Halsted is a Boystown branch of downtown’s popular piano bar, favored for happy hour and later for live cabaret. Leather-and-Levi’s types cruise the Cell Block. Steamworks Chicago is a popular, clean, well-run sauna – it’s one of the nicest such facilities in the country.

You can continue your clubbing in funky Andersonville, which is the heart of the city’s lesbian scene but also home to a few men’s (mostly hard-core) leather bars, such as the Chicago Eagle, which is attached to a bathhouse and decorated like a motorcycle garage.

Women and their friends flock to Star Gaze, the neighborhood’s top lesbian club, which serves dinner and also has DJs on weekends, lesbian comedy and live-music nights, and a convivial beer garden. Atmosphere is a lively dance bar and lounge with a mixed gay male and lesbian crowd. And Andersonville is also home to a branch of the gay-oriented franchise, Hamburger Mary’s, a dapper two-level space that’s popular both as a gay bar and a fine place to eat. Stop by on Wednesdays nights for “Mary-Oke” karaoke fun, perhaps after feasting on a Barbra-Q-Bacon cheeseburger with cheddar, Jack cheese, and a tangy-smoky sauce.

One of the most talked-about new eateries in the area, Anteprima turns out superb modern Italian fare and has a warm dining room with pressed-tin ceilings and a shaded patio in back. Don’t pass up the grilled quail marinated in honey with balsamic vinegar and pancetta. A lively and atmospheric bistro with a decidedly queer following, Tomboy serves tempting fare like pan-seared duck with crimini mushrooms and a port glaze. T’s is a friendly, gay-popular restaurant and bar – it’s a favorite lesbian date spot, known for healthful American food.

Taste of Heaven Bakery is a great pick for delectable breakfasts and lunches, plus fresh-baked snacks throughout the day – the fried-egg sandwiches and peaches-and-cream French toast are favorites in the morning. Another wonderful spot to satisfy your sugar fix is Sweet Occasions, which serves some of the thickest and richest ice cream in the city, plus fantastic cupcakes, cherry cobbler, and homemade fudge. It’s hard not to love this old-fashioned parlor with ice-cream sundaes named for the seven deadly sins. The “Lust” (a chipotle brownie topped with cinnamon ice cream, hot fudge, whipped cream, and red hots) may leave you lusting for another trip to these two charming Chicago neighborhoods.

Related: Chicago