Chicago Gay Guide - Chicago 2017 Events Calendar

Halsted Street, Boystown, Chicago
photo by Andrew Collins

Gay Chicago in a Nutshell:

A world-class centers of culture, commerce, education, architecture, dining, and shopping, Chicago is America's largest city after New York and Los Angeles, and it has a visible, active gay and lesbian community that you'd expect of such a place. You could easily travel here, spending all your time downtown at a conference or taking in the major attractions, and never see gay Chicago, which is centered around the Lakeview (Boystown) and Andersonville neighborhoods, about 5 to 7 miles northwest of downtown, but easily accessible via mass transit. This is a city of neighborhoods, so plan to venture outside the city core.

The Seasons:

Chicago's a great year-round destination, although winters can see spells of intensely cold weather, and summers sometimes bring sultry heatwaves. Fall and spring are when the odds favor moderate temperatures and pleasant days. Chicago has a number of festivals and events from spring through fall, and it's a big convention city year-round - hotel rates can soar when meetings are in town.

Average high-low temps are 32F/18F in Jan., 59F/42F in Apr., 84F/66F in July, and 64F/46F in Oct. Precipitation averages 2 to 4 inches/mo. year-round, with sometimes very heavy snowfall in winter.

The Location:

It may be in the Midwest, many miles from the nearest ocean, but Chicago is most definitely one of the nation's great waterfront destination, as it sits directly on rippling Lake Michigan - it's more than 50 miles across the lake to the state of Michigan. Chicago is in northeastern Illinois and surrounded mostly by flat suburbs and prairies, so apart from the lake, the setting is rather prosaic. The Chicago River cuts through downtown and is crossed by several scenic bridges. The city is a major interstate crossroads, traversed by such major roads as I-90, I-80, and I-94.

Driving Distances:

Driving distances to Chicago from prominent places and points of interest are:

Cincinnati, OH: 300 mi (4.5 hrs)
Cleveland, OH: 345 mi (5 hrs)
Columbus, OH: 355 mi (5.5 to 6 hrs)
Des Moines, IA: 330 mi (4.5 to 5 hrs)
Detroit, MI: 285 mi (4 to 4.5 hrs)
Indianapolis, IN: 185 mi (3 hrs)
Kansas City, MO: 530 mi (7.5 to 8.5 hrs)
Louisville, KY: 300 mi (4.5 hrs)
Madison, WI: 150 mi (2 to 2.5 hrs)
Milwaukee, WI: 90 mi (90 min)
Minneapolis/St. Paul, MN: 408 mi (5.5 to 6 hrs)
Nashville, TN: 510 mi (7 to 8 hrs)
Pittsburgh, PA: 460 mi (6.5 to 7.5 hrs)
St. Louis, MO: 300 mi (4.5 hrs)
Saugatuck, MI: 140 mi (2.5 hrs)

Flying to Chicago:

Chicago is served by two major airports. O'Hare, the larger one with scads of domestic and international flights (it's a hub for American and United), and Midway Airport, which is a bit smaller and a hub for Southwest Airlines. Although it's 90 minutes north, another option is General Mitchell International Airport, in Milwaukee, which is a clean, first-rate, beautiful facility that's much more pleasant than either Chicago airport. There's bus service from Milwaukee's airport to Chicago, and extensive ground transportation from the Chicago airports into the city, from hotel shuttles to train.

Taking a Train or Bus to Chicago:

It's very easy to get to Chicago by train or bus, and also easy to get around the city via public transportation via the various Chicago Transit Authority (CTA modes, including elevated rail ("the L"), bus, and train. You don't need a car to see Chicago, and most hotels charge sky-high prices to garage them, so stick with mass transit if at all possible (and the occasional cab as needed - these are plentiful). The city is easily reached via Amtrak train service and Greyhound Bus from such major Midwest cities as Indianapolis, Milwaukee, Minneapolis, and St. Louis

Chicago Festivals and Events Calendar 2017-2018:

Chicago GLBT and Travel Resources:

A number of resources out there offer extensive information on the city's gay scene, including The Windy City Times, which also publishes such niche gay publications as Nightspots, Identity, BLACKlines, and En La Vida; and Gay Chicago Magazine. is great for news about local gay scene, as is Chicago Pride. Also check out the popular alternative newsweeklies, such as the Chicago Reader, and the useful Chicago Magazine. The best city daily is the Chicago Tribune. The Center on Halsted, Chicago's GLBT community center, is a great help. Also check out the excellent GLBT site produced by Chicago Tourism.

Top Chicago Attractions:

Chicago Cultural Center

Gay-Popular Chicago Neighborhoods:

Lakeview (aka "Boystown"): Lakeview, about 5 miles northwest of downtown, runs between the lakefront and Ashland Avenue, north of Belmont Avenue up to Irving Park Road. Within this neighborhood is a small triangle east of Belmont Avenue called Boystown. Over the years the neighborhood has become a mix of artsy types; working-class families; young, not-yet-rolling-in-dough professionals; and gays (with a considerably more male than female presence). More recently, real estate values here have risen, and Lakeview has become increasingly more upscale, and more mixed gay/straight.

In the heart of Lakeview is Wrigley Field, home of baseball's Chicago Cubs. The vintage stadium draws thousands of fans on game days. Clark Street, which runs diagonally north-south, is Lakeview's major commercial thoroughfare, with a diverse collection of businesses, from spiffy bistros, ethnic restaurants, and simple fast-food joints to storefront theaters to sports-memorabilia shops and vintage clothing boutiques. Halsted Street, parallel to Clark just one block east, has the bulk of Lakeview's gay businesses, including dozens of boutiques, restaurants, and bars. You'll find still more gay-popular businesses along Broadway, which also runs parallel to Halsted and is a few blocks east, not far from Lake Shore Drive and the Lake Michigan waterfront.

Andersonville: One of several distinct communities within the northside of Chicago's diverse Uptown area, Andersonville was originally settled by the Swedes, then increasing numbers of Middle Easterners. But since the 1990s, it's become Chicago's most lesbian-identified neighborhood, and also a popular area to live and play among many gay men. The main commercial strip is Clark Street, has a great mix of ethnic restaurants, gay and lesbian bars and cafes, and prosaic workaday shopfronts. It's not as flashy or upscale as Lakeview, 2 miles south, and its adherents like the truly varied mix of residents and streetlife.

Wicker Park and Bucktown: West of Lincoln Park are the hip neighborhoods of Wicker Park and Bucktown. Originally home to immigrant Poles, Ukrainians, and other Eastern Europeans, then later to Puerto Ricans, these areas are a hodgepodge of ethnicities and lifestyles. The blocks around the threeway intersection of North, Damen, and Milwaukee avenues contain a bevy of hipster bars and restaurants, second-hand clothiers, galleries, and cutting-edge design shops. It's arguably Chicago's coolest neighborhood, although continuing up Milwaukee Avenue a few more stops on the L or a 15-minute walk Logan Square has also rapidly developed a cool and artsy scene.

Was this page helpful?