Chicago Gay City Guide: A Midwestern Jewel for the LGBTQ Community

Nestled on the shores of Lake Michigan, Chicago is an industrious metropolis that’s an exciting place for the LGBTQ community. An international hub of culture, commerce, and creativity, the city provides a multitude of gay resources to make every new resident feel at home.

A Brief History of the Windy City

Like many Midwestern regions, the Native Americans were responsible for cultivating a lot of the land. The actual term “Chicago” is roughly translated from a Native American word that means “wild onion,” something which grows abundantly to this day.

The city was born in 1883 and in 1983, Chicago saw its first black mayor. In 2019, for the first time in history, all three city-wide elective offices were held by women. Chicago is a forward-thinking and progressive town that has a lot to offer LGBTQ residents.

Quick Stats About the 312

  • The city is 227.63 square miles.
  • Chicago has both a commuter rail and rapid transit system. (Metra and cta).
  • Chicago is the third-most populous city in the United States (approx. 2,705,994 people).
  • Spray paint was invented in Chicago.
  • Chicago has over 20 nicknames.

Here are some more fun facts about Chicago.

The Chi-Town LGBTQ Community

Center on Halsted

This is the official LGBTQ community center of Chicago. It is the largest in the Midwest with over a thousand visitors each day.

LGBT Chamber of Commerce of Illinois

This place is working to promote equal economic opportunities for the LGBTQ community in the city of Chicago and the surrounding state. They do this by advocating with local businesses and networking like a boss!

Distinct Seasons

Chicago is a city with four very separate seasons. It is officially classified as hot-summer humid continental. Depending on where you live, there can also be a nice breeze from Lake Michigan. (That could also be a curse in the winter).

Most of the LGBTQ neighborhoods are near water, so keep that in mind. The more inland you go, the hotter the temps will be. Annual precipitation is average, and winters can get extremely cold (record being -15 degrees). However, summers are amazing, and autumns are mild and pleasant.

Key LGBTQ Events in the City

Chicago Pride Parade – June

This annual event is not to be missed! Held in Boystown every year, it’s one of the largest pride celebrations in the world, with over a million people in attendance.

Market Days - August

An annual street festival that features live music, food, booths, local artists, crafts, and more. Market Days is a huge event and tons of fun.

The Best Chicago Neighborhoods


The Boystown neighborhood in Chicago is home to one of the largest LGBTQ communities in the Midwest. The bustling neighborhood in West Lakeview has been hosting the Chicago Pride Parade since 1971and is full of charming boutiques, cool coffee shops, and trendy clubs.

The neighborhood is bordered by tree-lined Halsted Street on the north side of the city and is home to comedy clubs, theaters, and a young and vibrant nightlife. The Chicago Diner is also in Boystown which is the city’s oldest vegan restaurant.

The median price of homes listed right now in Lakeview is $473,836. The median cost per square foot is $353. That’s higher than the Chicago average of $240.

Boystown also has the award-winning Legacy Walk and boasts the world’s only outdoor LGBTQ history museum.


Labeled “Girlstown” in the 90s due to a vibrant lesbian population, Andersonville is a thriving LGBTQ community that’s nestled between Edgewater and Uptown. The neighborhood is located on the north side of the city with most of the action taking place between Clark Street and Ashland Avenue.

The community also has a Swedish heritage with the Swedish American Museum being a main cultural attraction. This also means the neighborhood is full of delectable bakeries and cute cafes.

The median price of homes listed right now in Andersonville is $451,443. The area is known for its 19th-century row houses and European architecture.

Andersonville is also home to Women and Children First, one of the largest feminist bookstores in the United States. They’ve been bringing LGBTQ-friendly literature to Chicago since the 70s.


In the past, the Pilsen neighborhood has been known as the center of the Latino community in Chicago. It’s now an up-and-coming LGBTQ community that’s welcoming to all. The urban enclave sits a little southwest of downtown, just below Little Italy and the Near West Side.

The median price of homes listed right now in Pilsen is $306,545. The long history is written in the neo-bohemian buildings, upscale lofts, and colorful murals.  

Pilsen is artsy. Enthusiasts should appreciate the National Museum of Mexican Art, which offers free admission, as well as eclectic eateries, diverse crowds, boutiques, and bars.

Ready to look at some "for sale" homes in Chicago? Connect with a top Chicago Gay Realtor today!

Getting Artsy in the City

The Art Institute of Chicago

Downtown Chicago's #1 rated art museum is the Art Institute of Chicago. Established in 1967, it's one of the world's larget venues for contemporary art.

Museum Of Contemporary Art Chicago

This modern art museum is located right near Water Tower Place in downtown Chicago. Established in 1967, it’s one of the world’s largest venues for contemporary art.

Parks and Recreation

Lincoln Park

Chicago has over 7,500 acres of parks in the city, but Lincoln Park is the biggest. There’s lots to do there from a driving range to the Lincoln Park Conservatory. The park has quaint footbridges and waterfalls speckled throughout and is the perfect place for a jog or to bring your furry friend.

Jane Addams Hull-House Museum

A social justice pioneer and suffragette, Jane Addams brought attention to poverty, public health, child labor, race relations, and adverse working conditions. In 1931, she was the second woman to receive a Nobel Peace Prize.

Amazing Nightlife


A multi-level gay club with a rooftop deck that has incredible views. Showtune nights and drag shows happen throughout the week.

Kit Kat Lounge & Supper Club

An upscale American restaurant with a lengthy cocktail menu. At this lively club, drag queen divas perform on a nightly basis.

Replay Beer & Bourbon

If you just want to have fun, Replay offers vintage video games with a funky arcade bar, beer, and cocktails. Located in Lakeview, it’s in the center of the LGBTQ community.

The LGBTQ community in Chicago continues to evolve. You can see evidence of this in thriving neighborhoods like Pilsner. If you enjoy good food, friends, arts, and everything an urban paradise has to offer, make Chicago your home.

Connect with a Chicago Gay Realtor for a no obligation conversation today!