Traveling to Chicago for a weekend trip is easy and affordable. Spirit, United, and Southwest airlines offer round-trip tickets from Baltimore to Chicago starting at $140 if your timing is right. Chicago has two airports and both offer public transport to downtown. Chicago is the third-most populous city in the US and a major business center. Its famous nickname “Windy City” comes from the frigid breezes that blow off Lake Michigan and go through the city’s streets – though some say the moniker references Chicago politicians, deemed to be “full of hot air.” Famous landmarks include the Millennium Park, Grant Park (where former President Obama gave his acceptance speech on November 4th, 2008), Navy Pier, the Willis (Sears) Tower, the Magnificent Mile, and the Art Institute of Chicago. Chicago is popular for its history, its city planning and development, and its cultural diversity – of which the city’s large gay community is a glittering jewel.

Chicago’s first permanent resident was a trader named Jean Baptiste Point du Sable, a free black man from Haiti, who came to the city in the late 1770s. In 1795, the US military built Fort Dearborn, but it was later destroyed by Native Americans. Chicago played a major role in the early westward expansion by the completion of the Illinois and Michigan Canal in 1848 because it created a water link between the Great Lakes and the Mississippi River. In 1871, the “Great Fire” destroyed most of Chicago’s buildings, streets, and sidewalks (because they were made of wood). Chicago rebuilt and many immigrants came to Chicago to take jobs in meatpacking plants and other factories. Prohibition (the alcohol ban from 1920 to 1933 – the drug war of its day) spawned famous Chicago gangsters such as Al Capone and Bugs Moran who wreaked havoc on the city.

Chicago is the first city in the US to have a skyscraper. The ten-story, steel-framed Home Insurance Building debuted 1884 and was demolished in 1931. In 1969, the John Hancock Center opened and it is now Chicago’s second tallest building. In 1973 the 1,450-foot Willis (Sears) Tower opened, and it remains the tallest building in North America and the third tallest in the world. The Aon Center is Chicago’s third largest building at 1,136 feet. It was completed in 1973 and was originally clad with Carrara marble, but due to Chicago’s harsh weather conditions, it had to be resurfaced with white granite in the early 90s. Chicago has many more architectural marvels and they can be seen on the famous Chicago Architecture River Cruise.

Chicago is also the first city to develop a reverse water flow system, forcing an about-face on the Chicago River, sending it toward the Mississippi River instead of Lake Michigan. This stopped the waterborne illnesses plagueing the city; however, the polluted water would become a headache (and stomachache) for the cities downstream dependent on Mississippi water.

The Chicago gay scene is huge. Northalsted Market Days ( just celebrated 36 years as an event that brings Chicago’s gay community out on the streets. Chicago offers a vast variety of gay bars and clubs. Sidetrack is a large popular club that draws a diverse crowd and is known for its showtune nights. Roscoe’s is a neighborhood bar with a dance floor, pool tables, and an outdoor area. Hydrate is a lounge and dance club that offers theme nights. Jackhammer is a multilevel club with dance bars that serves strong drinks. Berlin is a cavernous club with rollicking nightlife and a diverse crowd. Big Chicks is a lively bar with art-lined walls. The famous leather bar Cellblock offers pool tables and theme nights. Touche, another leather bar, offers strong drinks and a place to meet new people. North End is a longtime, low-key gay sports bar with flat-screen TVs and karaoke. The Phoenix is a popular gay suburban hangout. The Closet– a tiny, unpretentious lesbian bar– features dancing, games, and karaoke. Little Jim’s Tavern, a famous neighborhood venue, has been open since 1975. Baton Show Lounge, a bar known for its nightly drag shows, is also popular for its bachelorette parties. Second Story Bar, a small old-school watering hole, is tucked away above the Sayat Nova restaurant. Club Krave, a fun nightspot, offers dancing, karaoke, drag shows, and game nights. Mary’s Attic is a nice little bar above Hamburger Mary’s. And this list only scratches the surface!

For more info on gay Chicago a good starting point is the Center on Halsted, the city’s LGBT community center: or 773-472-6469.