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LGBT Travel Destinations: Why you should go to Chicago

by | Jul 6, 2023

Looking for amazing LGBTQ travel destinations?

Chicago stands out as one of the safest and most enjoyable travel destinations for the LGBTQ+ community in the United States. The city has long been a hub for inclusivity, championing diversity and equal rights, which is reflected in the day-to-day life and atmosphere of the city. 

A gay man staying by a rainbow-painted Chicago sign in the Northalstad neighborhood in Chicago, Illinois.

From its vibrant Boystown neighborhood, America’s first officially recognized gay village, to the bustling Andersonville that was historically home to the Swedish but has now become known for its queer culture, the city offers plenty of welcoming spaces for the LGBTQ+ community. 

Chicago’s residents are incredibly friendly and accepting, renowned for their Midwestern hospitality, creating an environment that is not only safe but extremely inviting for queer visitors.

A gay man atop the Willis Tower in Chicago, Illinois.

Chicago’s commitment to being an inclusive city is reflected in the numerous events and festivals it hosts that celebrate LGBTQ+ culture. 

Among the most notable is the annual Pride Parade, an event that has grown exponentially since its inception in 1970 and now draws a crowd of millions, making it one of the most prominent Pride celebrations in the world. Moreover, the city offers a variety of LGBTQ+-friendly activities and venues, including the Center on Halsted, the Midwest’s largest community center dedicated to LGBTQ+ people, and the annual Reeling Film Festival, one of the longest-running international LGBTQ+ film events.

In terms of acceptance, the city has consistently been at the forefront of LGBTQ+ rights. Chicago is known for its strong anti-discrimination laws, which protect individuals based on sexual orientation and gender identity in areas such as housing, employment, and public accommodations. 

A man leaning on the #amazingforall sign in Chicago, Illinois.

Beyond legal protections, the city has cultivated a culture of acceptance and allyship. The community spirit in Chicago is palpable, and it extends wholeheartedly to the LGBTQ+ population. 

This combination of legal protection, public support, and an array of social and cultural attractions make Chicago a haven for LGBTQ+ individuals and a top choice for travelers seeking a safe, inclusive, and fun destination.

Here’s what you can get up to if you choose visit Chicago – we promise it’ll have you booking your tickets and packing your bags!

Drag Brunch at Lark 

The ambiance at Lark is modern, welcoming, and full of life – an ideal spot for romantic evenings, social gatherings, casual weekday meals, or lively family brunches on the weekend. 

 A drag queen and go go dancer stop near a table of friends during a drag brunch at Lark Restaurant in Chicago, Illinois.

Their culinary focus is on authentic Neapolitan pizza, cooked to perfection in a wood-fired oven. 

Pizzas from a wood oven at Lark Restaurant in Chicago, Illinois.

Alongside this, they serve superb burgers, delightful sandwiches, and sumptuous pasta dishes, supplemented by a night owl menu for the late hours. 

The bar at Lark Restaurant.

You’ll find our beautifully crafted oak bar, polished to a rich walnut finish, showcasing a selection of 15 artisanal beers, perfect to enjoy while lounging near our warm, intimate fireplace. 

A group of friend enjoying drag brunch at Lark Restaurant in Chicago.

Alternatively, you can sample one of their expertly mixed cocktails in the open-air comfort of our award-winning patio. They also host exciting drag brunches every Sunday featuring regular performances.

Avocado toast at Lark Restaurant in Chicago.

View the menu and make a reservation at Lark: http://larkchicago.com

Visit one of Chicago’s historical LGBTQ destinations: the Leather Archives and Museum 

In 1991, Chuck Renslow and Tony DeBlase established the Leather Archives & Museum as a community resource to document, preserve, and share the history and culture of leather, kink, fetish, and BDSM.

Leather vests on display at the Leather Archives and Museum in Chicago, Illinois.

This institution houses an extensive collection of items from the gay leather and kink community, including but not limited to leather vests, badges, posters, and signs, as well as various other pieces of memorabilia. These artifacts and exhibits thoughtfully capture and conserve this significant segment of gay culture.

The resource library at the Leather Archives and Museum in Chicago.

In response to the recent wave of book restrictions sweeping across America, the Leather Archives and Museum maintains an impressive collection of LGBTQ+ literature. This spans various genres, from sex education and travel guides to adult entertainment and fetish-related works, including both fiction and non-fiction.

The auditorium theatre at the Chicago Leather Archives and Museum.

Moreover, the venue is equipped with a spacious auditorium used for hosting various events and lectures. The Leather Archives and Museum frequently invites researchers with interests in queer history and anthropology, providing them an opportunity to delve deeper into the nuances of gay leather and kink culture.

Gay culture memorabilia on display at the Leather Archives and Museum in Chicago, Illinois.

Make plans to visit the Leather Archives and Museum: http://leatherarchives.org

Enjoy at Day at the Gay Beach 

Often referred to as Hollywood Beach, but officially named Kathy Osterman Beach on Google Maps, this is a popular gathering spot for the gay community during the warm, sun-filled summer days. 

Hollywood Beach Pierced Light, at the gay beach, painted with a rainbow Pride Flag in Chicago, Illinois.

It boasts stunning sandy shores, a serene spot for contemplation at the AIDS memorial, and the distinctive Hollywood Beach Pierhead Light — a favored backdrop for striking selfie opportunities.

Hollywood Beach Pierced Light, at the gay beach, painted with a rainbow Pride Flag in Chicago, Illinois.

Dance at Scarlet in Northalstead 

Positioned within the Northalstead neighborhood, the epicenter of Chicago’s most vibrant gay district, Scarlet is a leading gay dance bar that has been a staple of the community for 15 years. 

A bartender pouring drinks at Scarlet gay bar in Chicago, Illinois.

This nostalgically designed establishment offers a prime setting for memorable selfies with friends during a night of revelry. Its dance floor is always lively, featuring DJs spinning an array of upbeat tracks. 

A neon sign and artwork on the wall at Scarlet gay bar in Chicago, Illinois.

The bar provides prompt service and offers a wide range of drinks, from basic to high-end spirits, ensuring your beverage needs are met whether it’s early in the evening or the late-night hours.

Check out the upcoming events and DJ’s: http://www.scarletchicago.com

Be Gay, Your Way, at Sidetrack in Northalstead  

Sidetrack, the cornerstone of the Northalstead gay district, has been serving the community since its inception as a single-room pub in 1982. 

A group of friends having beer at Sidetrack gay bar in Chicago, Illinois.

Known originally as Main Bar, it has transformed over the past four decades, taking advantage of ending neighboring leases to evolve into a multi-tiered complex with eight distinct rooms capable of accommodating over 1,000 guests. At Sidetrack, guests always enjoy free entry.

A group of friends having beer at Sidetrack gay bar in Chicago, Illinois.

From its beginnings, Sidetrack has operated as a video bar. It initially played videos on VHS, then transitioned to DVD/BluRay, and now utilizes a comprehensive digital music and video streaming system across the entire establishment.

A row of Stoli vodka bottles above a bar inside Sidetrack gay bar in Chicago.

At Sidetrack, there’s something for everyone, whether it’s relaxing on the ample rooftop deck during the day, enjoying music videos in the glass bar, watching captivating drag shows in the evening, savoring cocktails at the newly renovated NorthBar, or getting lost in the rhythm on the dance floor. 

A group of friends on the rooftop deck of Sidetrack gay bar in Chicago.

Weekly events cater to a range of interests, from trivia and drag shows to sing-alongs and RuPaul’s Drag Race viewing parties. While you might spot the occasional bachelorette party, daily programming ensures Sidetrack remains an authentic LGBTQ+ bar.

A group of friends on the rooftop deck of Sidetrack gay bar in Chicago.

This establishment has been a steadfast pillar in the Northalstead community, fighting to maintain its identity as a gay bar and regularly hosting fundraisers for local causes. Moreover, the team takes pride in being an LGBTQ+-majority staff and offers a health insurance program to ensure access to health benefits. Sidetrack remains a must-visit destination for queer travelers visiting Chicago.

Nobody’s Darling

A bartender making craft cocktail at Nobody's Darling, a lesbian-owned bar in Chicago, Illinois.

For a different atmosphere, consider Nobody’s Darling, a Black lesbian-owned bar in Andersonville, founded in 2021 by two friends passionate about golf and craft cocktails, Angela and Renauda. Their goal was to create an upscale, inspirational space offering unique cocktails. 

This space is not only affirming and welcoming, but it also stands out as one of the few bars in the U.S. predominantly serving spirits from businesses owned by people of color or women.

Nestled in the semi-residential Andersonville district, Chicago’s second-largest gay neighborhood, Nobody’s Darling has been a welcomed addition to the community. Whether offering simple gin and tonics or more sophisticated cocktails, the establishment has prospered and recently expanded its event space. 

Owners Angela and Renauda are deeply committed to their community, setting up a $10,000 fund for monetary and in-kind donations, and regularly host fundraisers to benefit the local LGBTQ+ community.

Visiting both Sidetrack and Nobody’s Darling doesn’t just offer you a memorable night out in Chicago, it also gives you an opportunity to stand with and support the LGBTQ+ community. 

With their warm, welcoming environments, these establishments promise not only unique experiences but also a chance to be part of a close-knit community that upholds acceptance, inclusivity, and freedom of expression.

See what all the fuss is about: http://www.nobodysdarlingbar.com

Visit them on your trip so we can expand and create more LGBTQ travel destinations

By choosing to spend your time in these establishments, you contribute directly to their efforts to maintain vibrant, safe spaces for the LGBTQ+ community. Your patronage helps these businesses continue their advocacy work and community outreach. This includes fundraising for local causes, providing safe spaces for events and parties, and creating jobs that respect and affirm the identities of LGBTQ+ individuals.

Two gay guys on the rooftop bar at Sidetracks in Chicago, Illinois with a rainbow heart in the background that says "Say Gay".

Your enjoyment at these venues transcends the typical bar experience; it directly supports their capacity to give back to the community. Whether you’re dancing the night away at Sidetrack, sipping a craft cocktail at Nobody’s Darling, or participating in their special events, you’re not only creating unforgettable memories but also helping to enrich the Chicago LGBTQ+ community.

Friends having colorful cocktails at the rooftop bar at the Virgin Hotel Chicago.

So next time you’re planning a night out or a trip to Chicago, consider Sidetrack and Nobody’s Darling. Enjoy a good time while making a meaningful difference. Stand with us, dance with us, and help us continue to create an accepting, vibrant, and thriving LGBTQ+ community in Chicago.

Epic Adventures and Must-Do Activities in Chicago

Chicago Architecture Foundation Center River Cruise

A visit to the Windy City would be incomplete without experiencing the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. This tour has earned the distinction of being ranked the top-rated tour in Chicago according to TripAdvisor reviews.

A gay guy standing near a Progressive Pride flag on the Chicago Architecture Foundation Center River Cruise.

Begin your journey on Chicago’s First Lady Cruises, a two-story riverboat that sails up the Chicago River, exploring both its left and right branches before venturing into Lake Michigan. This expedition offers awe-inspiring vistas of Chicago’s skyline.

Sailing up the Chicago River on a Chicago architecture river cruise.

The experience is further enhanced by a volunteer narrator who vividly shares the history and stories behind the buildings lining the riverfront and their significance in Chicago’s evolution and regeneration.

Sailing up the Chicago River on a Chicago architecture river cruise.

In addition, you’ll gain insight into the city’s ongoing initiatives to create ‘river walks’ – pedestrian paths along the river that will eventually form a unified network. Learn about the transformation of the Chicago River, from its former use as a dumping site to its current status as a vibrant, thriving lifeline of the city.

More than just an educational journey, this river cruise provides an opportunity to unwind, soak up some sun on the rooftop deck, enjoy a cocktail, and capture photographs of Chicago from unparalleled vantage points. Whether you’re a history buff or simply seeking a unique way to explore the city, this tour promises an engaging and enjoyable experience.

Sailing up the Chicago River on a Chicago architecture river cruise.

Book your Chicago architecture river cruise now: www.cruisechicago.com/tours/architecture

SkyDeck Chicago at Willis Town with Chicago CityPASS 

Perched atop the renowned Willis Tower, Skydeck Chicago holds the title of being the tallest observatory deck in the United States. On a clear day, you can feast your eyes on panoramic views stretching across four states and up to 50 miles. 

a view of downtown Chicago from the Willis Tower.

Alongside The Ledge, an extension that juts out 4.3 feet from the Willis Tower, Skydeck also boasts a recently added interactive museum experience on its lower level. With your Chicago CityPASS, you can enjoy expedited and priority access to the spectacular SkyDeck Chicago.

a view of downtown Chicago from the Willis Tower.

Venture out onto the observation deck of not only Chicago’s tallest building but the third tallest in the Western Hemisphere! While the tower offers breathtaking views that can span up to four states, a unique feature, The Ledge, a glass balcony, provides a thrilling experience, extending four feet beyond the 103rd floor of the Willis Tower. 

The glass enclosures of The Ledge extend 4.3 feet from the SkyDeck, taking you to a dizzying height of 1,353 feet.

A gay man sitting on the SkyDeck at the top of the Willis Tower in Chicago, Illinois.

The Ledge at the SkyDeck provides a heart-stopping, adrenaline-pumping experience as you step onto the glass platform, 1,353 feet high and 4.3 feet away from the tower, supported only by a 1.5-inch-thick glass.

Looking up at the Willis Tower in Chicago, Illinois.

Furthermore, the observatory tower now features an engaging 30–60-minute interactive experience, offering a deep dive into Chicago’s highlights and the fascinating history of its tallest building. 

For those pondering over what to do in Chicago that combines fun and learning, this interactive museum experience is an excellent addition to your visit to the 103rd-floor Skydeck.

Experience all of this at a discounted price of 48% off on Expedited Entry Willis Tower Skydeck tickets, along with access to five other top Chicago attractions – offering unmatched value for your sightseeing adventure!

Learn more about the Skydeck Chicago experience: http://theskydeck.com

Get your Chicago CityPASS now: http://www.citypass.com/chicago

Plan to attend Chicago Pride Fest 2024

The Chicago Pride Fest is a highlight of the LGBTQ+ summer events in Chicago, drawing crowds from all over North America. Its unique blend of entertainment and ambience make it an unmissable occasion.

A drag queen performing on stage at Chicago Pride Fest 2023.

Not only does the event feature an extensive outdoor music festival celebrating the LGBTQ+ community, but it also provides an opportunity to explore one of the oldest gay neighborhoods in North America.

Eureka O'Hara performing on the main stage at Chicago Pride Fest 2023.

Partake in vibrant parties and ensure you don’t miss Chicago’s must-see attractions such as The Bean, an architecture river cruise, and the city’s famous deep-dish pizza. Whether you’re a first-timer, haven’t visited in a while, or are a seasoned attendee, it’s high time to mark down the 2024 Chicago Pride Fest in your calendar.

A DJ spins on stage for the crowds at Chicago Pride Fest 2023.

Read about Chicago Pride Fest 2023.

Dining Suggestions in Chicago

Morning coffee at Two Zero Three

Begin your day on a high note at Two Zero Three, located in Virgin Hotel Chicago. Nothing compares to starting the morning with an expertly brewed cup of coffee or a refreshing pre-breakfast beverage at this locale.

A hot latte from Two Zero Three coffee shop in the Virgin Hotel Chicago.

See the Two Zeo Three menu: www.virginhotels.com/chicago/dine-and-drink/two-zero-three

Breakfast at Elevate Coffee in Boystown 

Then, head over to Elevate Coffee in Boystown for breakfast. This cozy and welcoming coffee shop, operated by the LGBTQ community, takes pride in serving top-notch coffees, teas, sandwiches, and pastries.

With an appealing selection of lattes, sandwiches, and pastries, it’s an ideal place for a meet-up with friends in Boystown. The modern design of the coffee shop and its exceptionally friendly staff add to its charm. It has quickly become the go-to spot for dates in Boystown!

See the latest specials at Elevate Coffee: www.elevatecoffee.us

Lunch at Big Jones in Andersonville 

Experience the essence of Southern cooking through Big Jones’ celebrated culinary style, where regional Southern dishes are served in a laid-back dining atmosphere. 

The exterior of Big Jones restaurant in Andersonville, Chicago, Illinois.

They are renowned for their broad in-house charcuterie program, award-winning weekend brunch, and a full bar hosting over 100 American whiskeys. The farm-to-table ingredients, heirloom grains, and produce come together through the skillful hands of their family.

A pulled pork sandwich at Big Jones restaurant in Andersonville area of Chicago, Illinois.

Esteemed proudly-out gay chef Paul Fehribach infuses Chicago’s culinary landscape with an easygoing Southern vibe. Big Jones intertwines timeless Creole flavors with famous hospitality, all while offering an extensive selection of bourbons, scotches, and whiskeys.

Homemade biscuits at Big Jones restaurant in Andersonville.

Situated in Andersonville, one of the most extensive gay and lesbian communities in Chicago, this neighborhood is known for its varied local businesses and chic boutiques, creating a uniquely eccentric atmosphere.

The dining room inside Big Jones restaurant in Andersonville.

The bar at Big Jones is just as enticing as the food menu, with its handmade cocktails and thoughtfully curated wine and beer lists. One of Chicago’s most extensive Bourbon selections, carefully chosen family farm-produced wines, and local beers keep the offerings fresh and intriguing. Whether you’re seeking brunch, lunch, or dinner, the city’s best house-ground burger, or a unique dining experience, Big Jones delivers. 

Hightops by the bar at Big Jones restaurant in Andersonville.

It’s one of the LGBTQ travel destinations you simply cannot miss when you’re in Chicago. 

View the menu and make your reservation at Big Jones now: http://bigjoneschicago.com

Dinner at Miss Ricky’s Restaurant

Miss Ricky’s is an incredibly impressive establishment, exuding an enchanting aura that materializes precisely when it’s most needed. At this very moment, you find yourself in dire need of its presence. Miss Ricky’s embodies the essence of a mythical unicorn, poised to fulfill your every aspiration. 

The entryway neon sign at Miss Rocky's inside the Virgin Hotel Chicago.

Nestled on the ground floor of Virgin Hotels Chicago, Miss Ricky’s presents an array of delectable brunch choices, both within its inviting interiors and in the refreshing al fresco setting.

Dinner served at Miss Ricky's inside the Virgin Hotel Chicago.

View the menu and make your reservation: http://virginhotels.com/chicago/dine-and-drink/miss-rickys/

Stay at the LGBTQ+ Friendly Virgin Hotel Chicago 

Experience the unparalleled fusion of luxury, innovation, and vibrant energy at the distinguished Virgin Hotel in Chicago! Nestled in the heart of the bustling Windy City, this remarkable property radiates a distinctively chic and rebellious allure, setting it apart as a beacon among hotels. 

The Virgin Hotel Chicago with a Pride flag hanging out front.

The moment you step into the lobby, you’ll be enveloped in a contemporary and dynamic ambiance that effortlessly blends comfort with a touch of daring adventure.

A modern, queen size bed in a guest room at the Virgin Hotel Chicago.

The atmosphere at Virgin Hotel Chicago is truly electric! Sleek and vibrant designs adorn every nook and cranny, emanating a sense of modern elegance and exuberant energy that encapsulates the city’s spirit. 

Bathroom vanity in a guest room at the Virgin Hotel Chicago.

Whether you’re socializing with fellow guests or indulging in relaxation within your exquisitely appointed room, a palpable excitement will be ever-present, setting this hotel apart from the rest. With its prime location and unwavering commitment to exceptional service, Virgin Hotel Chicago ensures an unforgettable stay, where each guest is cherished and nurtured.

But that’s not all….

Embracing its LGBTQ+-friendly status goes beyond mere words at Virgin Hotel Chicago. Through tangible actions, such as comprehensive training programs and inclusive policies, the hotel creates a safe and welcoming haven for all guests, genuinely embracing the LGBTQ+ community. 

An outdoor communal table with a mural in the background, at the Virgin Hotel Chicago.

By actively supporting local organizations and events like Chicago Pride, the hotel wholeheartedly gives back to the LGBTQ+ community, exemplifying its dedication to fostering inclusivity and equality.

See why we think it’s the best lodging on your trip to one of North America’s best LGBTQ travel destinations.

Read more about the Virgin Hotel Chicago.

Make your travels to/from the Chicago O’Hare International Airport, extra!

Indulge in a lavish and stylish experience by reserving a chauffeur-driven sedan from Global Allure for your journey to and from Chicago O’Hare International Airport! Let us transport you in the epitome of luxury and sophistication, ensuring a seamless and remarkable travel experience.

Book your luxury ground transportation now: http://allurecanada.com

Is Chicago a Safe LGBT Travel destination? 

Amidst the shifting landscape of the current political climate in the United States, media reports often portray Chicago as one of the nation’s most dangerous cities. 

However, armed with this guide, your visit to Chicago will ensure a stay in safer communities and the opportunity to patronize LGBTQ+-friendly establishments.

Two friends posing in front of the iconic silver bean in Millennium Park, Chicago.

Illinois, up until now, has managed to steer clear of the drag bans, anti-trans and anti-gay legislation, and other pressing issues that have plagued various states across the country. 

Throughout its history, Chicago has served as a thriving hub for diversity and culture, naturally fostering an atmosphere of tolerance and friendliness. 

The city boasts a sizable and vibrant queer community, adding to its charm and inclusivity.

Choose Chicago as your LGBTQ travel destination

Chicago has a way of making everyone feel welcome. The LGBTQ+ communities, friendly residents, diverse nightlife, and year-long Pride celebrations make Chicago one of the most inclusive cities in the country. Come explore the historic landmarks, welcoming neighbourhoods and thriving nightlife scene. 

Chicago Pride Fest banner hanging over the 2023 festival entrance.

Pride is in Chicago’s DNA and they are excited to welcome you. Visit Chicago and discover why Condé Nast Traveler readers voted Chicago the Best Big City in the U.S. for a historic sixth year in a row!

A gay guy standing near a Progressive Pride flag on the Chicago Architecture Foundation Center River Cruise.

For more information, visit www.choosechicago.com and follow @choosechicago on Facebook, Instagram and Twitter. #ChicaGOandKNOW

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Brian Webb

Brian Webb

Author

Brian Webb is the founder and editor-in-chief of HomoCulture, a celebrated content creator, and winner of the prestigious Mr. Gay Canada – People’s Choice award.An avid traveler, Brian attends Pride events, festivals, street fairs, and LGBTQ friendly destinations through the HomoCulture Tour. He has developed a passion for discovering and sharing authentic lived experiences, educating about the LGBTQ community, and using both his photography and storytelling to produce inspiring content.Originally from the beautiful Okanagan Valley in the southern interior of British Columbia, Brian now lives in Vancouver, British Columbia. His personal interests include travel, photography, physical fitness, mixology, drag shows.
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