Skip to Content

Chicago Gay City Life, Events, Festivals & Gay Neighborhoods

Chicago Gay City Life, Events, Festivals & Gay Neighborhoods

Gay Chicago – City Guide to Pride and the Gay Neighborhoods. We have finally visited the world-famous city of wind in the American Mid West, Chicago. Especially for Karl, a dream came true when we were standing at the shore of the Chicago River surrounded by incredibly impressive skyscrapers and another top of the top architectural highlights of the third-biggest city of the USA. Suitably during pride month, we as gay couple travel bloggers were invited to attend Gay Pride in Chicago, the Pride Park Festival, and explore the gay neighborhoods of the city, Boystown and Andersonville.

– in paid collaboration –

But this is, of course, not everything you as an LGBTQ+ traveler should check out while traveling to Chicago and Illinois. Stay at one of the gay-friendly accommodations, sip on your cocktail at the world’s biggest rooftop terrace, have dinner at great queer-minded vegan restaurants or soak up the pretty boys while taking a swim in the refreshing waters of Lake Michigan at the Kathy Osterman Beach. Together with Enjoy Illinois and Choose Chicago, we created our Gay Chicago City Guide with tips and highlights for your perfect gaycation. Read all about Chicago Gay City here on Couple of Men.

Chicago Gay City Tipps Gay Couple holding hands in front of the Rainbow Balloons Chicago Gay Pride Parade 2019 ©
Chicago Gay Pride Parade 2019 ©

Gay Chicago City Guide – Pride & Gay Neighborhoods

Planning to come to see gay life and meet the LGBTQ+ community of Chicago, but wondering where to begin? We asked us the same questions before our gay travels to Illinois and Chicago but now after our 10-day trip, we’ve got the answers! It seemed to be the best way for us to split our trip into two parts: The first days, we spent in the northern part of Chicago which is supposed to be home to the gay neighborhoods Boystown and Andersonville. For part two of our trip, we decided to treat us with a centrally located gay-friendly hotel in Downtown Chicago to be able to see some of the highlights Chicago is famous for. One thing is for sure: Chicago knew how to impress us with spectacular culture, architecture, and a very welcoming and open-minded LGBTQ+ community! Chicago’s best gay parties in Boystown and beyond >

Flying with KLM Royal Dutch Airlines ©

How to get to Chicago?

Our favorite airline KLM Royal Dutch Airlines offers flights from €500* to Chicago. A special tip for German LGBTQ+ travelers: SkyTeam member KLM Royal Dutch Airlines with their modern fleet brings you comfortably and quickly from 10 German Airports via Amsterdam-Schiphol, the KLM hub, to over 160 destinations around the globe. *subject to availability / last check: September 2019

Plan & Book a Chicago Trip >

(Gay) Pride Chicago

Next Date: 28th June 2020 | Chicago – Boystown/ Andersonville

Lucky us, we could attend the 50th edition of the annual Chicago Pride Parade attracting every year again with approximately 750,000 people from all over the world. The parade is usually scheduled for the last Sunday in June, kicking off at Montrose Avenue and Broadway in Chicago Uptown and ending near the intersection of Diversey Parkway and Sheridan Road in Lincoln Park. We decided to start our day with a brunch at Drew’s on Halsted before joining the parade watching along Halsted Street, Belmont Avenue, and Grace Street. The rainbow crowd was very young with families and numerous queer and trans people screaming, dancing, and singing along the parade route.

Chicago Pride 2019

The parade was very protected and people other than participants of the floats and dancing groups were not allowed to walk the parade. We have never seen so many police officers on horses and rooftops. It is nice to feel safe on one hand, on the other, we wondered why Chicago Pride organized such a display of blue while other US cities are doing fine without all the extra marshals and fences protecting the route. Nevertheless, a great addition to the team as grand marshal was the first openly gay mayor of Chicago, Lori Lightfoot, who marched the parade together with her wife under loud cheering from the audience. Amazing! The Gay Chicago Parade was also in 2019, the 50th anniversary of its existence a huge success marking the climax of a whole festival week in Pride Month of June, although due to a big thunderstorm, the last 30 minutes of the parade had to be canceled. Emergency management officials advised attendees to take shelter and most people fled into shops and bars to stay dry and keep the party going.

Plan your Trip: Chicago Pride Calendar | Out & About in Illinois

Chicago Pride Fest

Dates: 19th to 21st of June 2020 | Chicago – Boystown

The weekend before the Chicago Pride Parade, the Chicago Pride Fest starts its celebration with a legendary block party and street festival on Halsted Street. The two-day street festival can be seen as the Pride opening event leading up to the Chicago Pride Parade a week later. In 2020, the LGBTQ+ celebration will celebrate its 20th anniversary with up to 100,000 people expected to attend. This year again, the streets were full of rainbow-colored party people celebrating love until the block party area closed. But don’t you worry, the party continued in the gay bars and clubs in the Lakeview neighborhood. We have never seen such a fierce and lively crowd during a street party. Although Pride Fest feels very family-friendly, we would suggest leaving small children at home and have the time of your life!

Plan your Trip: Chicago Pride FestLGBTQ+ Events in Chicago

Gay Travel Guide Illinois ©

Gay Travel Guide Illinois

The US State of Illinois in the Mid-West is known for Chicago, the natural beauty and beach of Lake Michigan, the beginning (or end) of the Route 66, the LGBTQ+ vacation gem Galena and, of course, the connection to the Mississippi. All you need to know for your gaycation in Illinois now on our Gay Travel Guide Illinois.

Plan your Trip to Illinois >

Gay Boystown – LGBTQ+ History & Community

One of the best ways to start exploring the gay neighborhood of Boystown is to plan a visit to the Center on Halsted. It is Midwest’s most comprehensive community center dedicated to building and strengthening the Lesbian, Gay, Bisexual, Transgender, and Queer community. Visitors learn about the history of Gay Chicago as well as the newest updates of the LGBTQ+ life. Another way of getting to know more about the LGBTQ+ history and the life and work of notable lesbian, gay, bisexual, or transgender individuals of Chicago and the USA is to join a tour of The Legacy Walk along with its 10 pairs of 25′-tall decorative “Rainbow Pylons”. Each of the pylons shows a bronze memorial plaque commemorating the achievements of those who have helped to shape the world – but whose contributions, sexual orientation, or gender identity have been overlooked, minimized, or redacted entirely from most historic texts.

Plan your Trip: Center on Halsted StreetThe Legacy Walk | Enjoy Illinois: Chicago Boystown

Gay Boystown – Gay Bars & Gay Clubs

Chicago’s Boystown truly is a rainbow-colored, open-minded, and diverse part of Chicago with multiple gay bars and clubs for every “kind of gay”. Some best-known bars are the following. North Halsted’s first gay bar was Little Jim’s Tavern which is big with the late-night crowd and features daily drink specials. Another fun and entertaining gay nightclub is Roscoe’s where gays and friends come to drink, dance, sing, watch videos, dine at their sidewalk patio or hang out by the fireplace or in the garden. Long known as one of Chicago’s premier gay clubs, Cell Block has a front bar, a dance floor as well as a DJ and live entertainment. For sports fans among the LGBTQ+ travelers, we recommend the gay sports bar North End. The gay bar is a neighborhood staple for more than 25 years, offering a pool, darts, all the games on giant flat screens, and a great beer selection. Named as Chicago’s best gay bar by several media outlets, Berlin is known as the best LGBTQ+ bar for the alternative scene. Last but not least, a place where Chicago comes to celebrate. Side Track proudly serves a unique mix of music video programming, multiple bar spaces, and world-famous frozen Cocktails.

Gay Bars & Clubs in Andersonville

The second popular gay neighborhood in Chicago with a large gay and lesbian community is called Andersonville and is located north of  Boystown. Anderson is known for its diversity and quirky atmosphere. The neighborhood is made up of many locally owned businesses and stylish boutiques as well as LGBTQ+ and gay-friendly bars and locations hosting some of the best gay parties in town. For example, Bearracuda, the largest attended bear dance party and most prolific gay dance event in the U.S. which we attended during Chicago Pride week at Jackhammer and The Call dance bar playing music that ranges from retro to pop and show tunes. A special tip for The Call is the themed video nights include Britney Spears videos all evening long on the last Friday of the month.

Plan your Trip: Enjoy Illinois: Chicago Andersonville

Gay-friendly Hotels & Accommodations

The city of Chicago has great accommodations to offer from luxurious 5+ star hotels to centrally located 4-star hotels and hostels. During our trip, we stayed in three different hotels in three different parts of the city. The first nights while exploring Boystown, we had a comfortable spacious suite at the Best Western Plus Hawthorne Terrace Hotel on Broadway the next street over to Halsted, the main street of Boystown. Part two of our trip brought us to Downtown Chicago where we spend some nights at the 4 Diamond Kimpton Gray Hotel on West Monroe Street. After our road trip to Galena and the northwest of Illinois, we spend a night at the Hilton Orrington/Evanston. We can recommend all three gay-friendly hotels in Chicago knowing there are even more!

Plan your Trip: BW Plus Hawthorne Terrace HotelKimpton Gray Hotel | Hilton Orrington/Evanston

Chicago through a Lesbian Couple’s Eyes

We were so excited that our friends and LGBTQ+ travel buddies Megan and Whitney from joined our trip to the American Mid-West. While our focus lays on gay-specific content, tips, and highlights, we would like to share their unique view of Gay Chicago, or, in their case, Lesbian Chicago! They are currently working on their Lesbian Travel Guide for Chicago so stay tuned on that as well!

Interesting Posts for your Gay Travels:

Gay Chicago City Guide – Explore Illinois LGBTQ+ Capital

Although Chicago is not the capital city of Illinois (that is Springfield), it truly is the LGBTQ+ capital of Illinois, maybe even of the American Mid-West. There was not a single moment we felt unsafe, or we faced homophobic behavior. The opposite was the case. Besides the pride festival and the gay neighborhoods, Chicago offers diversity throughout the city. Did you know that the world’s biggest rooftop bar is located in Chicago at the Navy Pier? We visited the rainbow location with its spectacular view over Chicago’s skyline on Pride Saturday getting a rainbow ice cream at the Original Rainbow Cone and watch the people riding the Ferris Wheel decorated with a huge rainbow flag. We will be back, hopefully soon, to show you even more of the third-biggest city of the United States of America.

Do you want to know more about our gay travels around the world? Stay tuned on Facebook, Twitter, YouTube, and Instagram. See you again soon!

Karl & Daan.

Do you like it? PIN IT!

Please note: This trip was made possible in close collaboration with Enjoy Illinois and KLM Royal Dutch Airlines as well as the tips and help from our wonderful readers, followers, new and old friends from all over the world. Nevertheless, our photos, our videos, our opinions, and our writings are our own, as always.