Gay Chicago

The great windy city of Chicago is truly a place that is a must-visit for any gay traveler. The city is filled with cultural and architecturally rich neighborhoods and gorgeously designed parks. There isn’t a better place on earth that holds all the pleasures of the gay traveler. Historical theater marquees and landmark skyscrapers loom over the magnificent downtown skyline, while numerous thriving cafes and boutiques lay directly under it. The populations of Lakeview and Anderson sections of the city invite travelers to ogle their window displays as they pass by sipping on hot and deliciously frothy espressos. Unlike coastal cities, Chicago has no beach, but that doesn’t seem to stop the sun-worshippers who gather at the numerous lakefront spots all over the city. Recently, Chicago was chosen to host the Gay Games which only served to boost the Cities reputation as a continually growing gay hub.

Check out Kylie Condon's travel journal exploring the lesbian culture in Chicago. Lez Explore: Chicago

If you’re a professional shopper or even a professional window-shopper, then you definitely do not want to miss the Magnificent Mile. The Magnificent Mile is truly a feat of wonder for you shopaholics; you will find an avenue lined with 460 different stores to feed your material cravings, and over 220 delicious restaurants to enjoy. This avenue should quell all of your shopping addictions, but if you’re looking for more, then head over to Wicker Park/Buck town for some out-of-this-world funky boutique shops and discount stores. Best of all, if you’re looking for a shop with a gay scene, then head over to Hollywood Beach, formerly known as Kathy Osterman Beach. This is where the gay scene is at!

Into sports? A gay jock? Chicago is a city you can’t afford to miss! Chicago hosts a myriad of sports franchises including: The White Sox, The Bears, The Cubs, and The Bulls. For a memory you can’t forget, head over to Wrigley field and feel the deep history that lies there as it is one of the oldest ball fields in the nation. Tickets don’t come cheap here, but it is still worth every penny.

Here is something that you might not know; Boystown, Chicago was the first officially recognized “gay village” in the nation when it became the central gay mecca in the 80’s. In the late eighties, Andersonville rivaled Boystown in attracting lesbians looking for an alternative gayborhood. Nowadays it is no longer segregated with homosexuals and lesbians living in both parts; and best of all, they all know how to have a good time!

Remember to pack accordingly before you make your trip to Chicago. The winters are harsh and the sun only comes out in April after 9 months of winter. After the sun comes out, the gayborhoods come to life with outdoor seating and gorgeous people flooding the streets. If you come before April, then you need to be sure to dress warm.

Give your family an iconic Chicago experience they won’t soon forget! Take in incredible views from the top of the Ferris Wheel at Navy Pier or The Ledge at Skydeck Chicago. Make your trip both fun and educational with a trip to the Field Museum, the Museum of Science and Industry, the Art Institute of Chicago or the Shedd Aquarium. Shop ‘til you drop along the Magnificent Mile with stops at American Girl Place and The LEGO Store at Water Tower Place.

Chicago Gay Scene

Chicago’s gay scene is divided into two gorgeous gayborhoods, Boystown and Andersonville. Boystown is located centrally next to Lake Michigan and to the east of Clark street. Boystown has two main streets that a traveler needs to know, Halsted and Broadway. The two main streets make up the heart of this extremely popular gayborhood in Boystown. Check out Halsted if you are in the mood for gay and lesbian bars and restaurants.

Andersonville is another area that is a must see for any dedicated gay traveler. This area is extremely popular with Chicago’s Gay scene. Compared to Boystown, Andersonville is considered to be much more diverse and eclectic and is comprised of mainly lesbians though you will find many homosexuals living there.

Recently Chicago was chosen to host the prestigious Gay Games, which further has boosted its reputation as one of America’s gayest cities. During the June and July months in Chicago there are two more Pride Celebrations. The first celebration lasts for a month and is a long series of LGBT events that launches with an extravagant weekend festival and parade. The second event is Chicago’s Windy City Black LGBT Pride Festival, which is a celebration of gay pride by the African American population living in the community.

Don’t forget that Chicago was the first city ever to be recognized with a “gay village”, which was in the eighties when all the homosexuals moved there. The “Gay village” became the central mecca for all gays in the nation during the eighties; it was truly a historic time period.

Gay-Friendly Dining

Chicago’s restaurant scene is world-class. If you feel so inclined, you can find gourmet hot dogs or the best deep dish pizza in the country, and that is just the tip of the iceberg. It doesn’t matter what kind of food you are looking for, Chicago probably does it best.

D.S. Tequila Company

D.S. is a perfect place to begin your night out on the town.  Offering a combination of Mexican and American fare, this place is bound to have something for almost everyone.  Not to mention, the perfect frozen margarita to pair with your meal.  Reasonably priced and incredibly delicious.  The house tequila is amazing as well, so you can’t go wrong.

The Walnut Room

Famous for its Chicken Pot Pies, the Walnut Room also offers gourmet American fare. For those of you with little ones, have no fear, the Walnut Room does have a children’s menu. If you’re visiting for Christmas Time, you must stop in to see the Great Tree, the 45 foot masterpiece exhibited in the center court of the dining room.


Great night out with friends or a romantic dinner for 2. The atmosphere is like being in a South American square. The wait staff is very helpful with recommendations and have never been wrong. Cocktails are a must try, along with their ceviche.

Gay-Friendly Nightlife

Chicago’s gay nightlife takes the cake. There is something for everyone from laid back gay bars to bumping gay clubs. A legendary night is out there just waiting to be had.


The SmartBar on Sunday nights is a great way to end the weekend and begin the week with both resident and guest house DJS. This is a mixed gay and straight friendly club on Sunday Nights. The vibe will remind you a lot of Euro Industrial House with very friendly mixed group and on some nights you'll be luck enough to see some flash backs to the Club Culture Kids.


Drink specials every night ALL NIGHT! 1920's influenced interior design and fun bartenders with a heavy hand. Get there a bit early or late come Friday and Saturday night(s) to avoid the line, but definitely get there!


Wanting to enjoy an intimate cocktail with a friend? Look no further than Elixir. This small capacity lounge is great! The bartenders take their time in crafting a cocktail especially for you. The price is a bit on the higher side, but the drinks are worth the price. Make sure to show up early, in order to have a seat!

Restaurants in Chicago

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Nightlife in Chicago

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Local Tips in Chicago

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