A Gay Guide to Chicago

A Gay Guide to Chicago

A gay guide to the Windy City

Sitting on the banks of Lake Michigan and holding the title of the third-largest city in the USA, Chicago is a location that is deeply entrenched in its culture and community. The people here are infamously outgoing and will make any visitor feel welcome.

With a backdrop of mesmerising contemporary architecture, expansive green spaces and flowing waterways, Chicago is a beautiful and enchanting city that is home to an increasingly vibrant art and culture scene and boasts one of the best restaurant industries in the USA. Filled with fascinating cultural and historical treasures, ‘the windy city’ has something to offer every gay traveler.

Chicago is home to one of the most exciting, vibrant and diverse gay scenes in the States and its gay neighbourhood of Boystown is a bustling district of nightlife, culture and community, boasting a wide range of gay clubs and bars as well as mutliple community organisations that seek to preserve and protect the area’s LGBT+ heritage.


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Gay bars and clubs in Chicago

The gay nightlife scene in Chicago tends to kick off late and stay busy until even later, with many of the clubs in the iconic Boystown remaining open until the early hours. The gay clubs and bars that make up this impressive gay scene are diverse, inclusive and offer a varied selection of clubbing opportunities for all tastes.

The focal point of Chicago’s gay scene and arguably the most popular gay bar in the city, Sidetrack boasts multiple clubbing spaces, a large dancefloor and an impressive rooftop deck. The club has become famous for its range of event nights, which include performances from Ru Paul’s Drag Race alumni, world-class cabaret acts and Tony Award screenings. Sidetrack is a must-visit destination for any gay traveler and the club can easily attract upwards of 1000 attendees on weekend and weekday nights.

Scarlet Bar puts pride at the front and centre of its mission. Resembling a gay bar from a bygone era, the vintage decor of the bar combined with the iconic pop playlist makes Scarlet one of the most liberating and fun gay bars in Chicago. Crowds flock to the bar for its renowned music, which is selected nightly by 5 resident DJs. Scarlet Bar gets most busy in the early evening as locals warm-up before heading to the city’s larger venues.

Gay travelers looking for a high-energy, neon-filled space to dance to pop classics should look no further than Hydrate. The club combines high-tech lighting and sound systems to create a one-of-a-kind clubbing experience, complete with shirtless dancers, amazing drink deals and nightly entertainment. Hydrate has also become known for hosting some of the best drag shows in the city, with local and touring queens routinely putting on world-class performances for the large crowds.

Gay hotels in Chicago

The majority of hotels in Chicago will be gay-friendly, and travelers should have no trouble when booking double rooms. However, undoubtedly the best place to stay is in the heart of the city’s gay community and the gay scene, Boystown.

City Suites Chicago is located in the heart of Boystown and offers guests a modern and comfortable stay just minutes away from the city’s hottest gay nightlife. The hotel is decorated with an art deco theme that gives the rooms a unique and personal feeling. City Suites Chicago is a very affordable option for guests wanting a central location and elegant interiors.

The rooftop lounge at The Robey is this hotel’s crowning glory. After taking a dip in the open-air pool, guests can enjoy the stunning and unparalleled views across Chicago’s skyline. The high-quality rooms at the hotel are furnished with design in mind, and each room boasts hardwood floors and beautifully tiled bathrooms. In the evening, guests can make the most of the on-site bar and restaurant that serve an array of local and international dishes.

Located just a five-minute walk from the beach, and offering easy access to busy Boystown, The Thompson Chicago offers guests the ideal base from which to explore the city and sample some of the world-class eateries that are located close by. Each spacious and airy rooms features a flat-screen TV, rain shower and breath-taking views across the Chicago skyline.



One of the most vibrant, community-oriented and passionate gay districts in the USA, Boystown was also the first to be officially recognised as a ‘gay village’. The area boasts an outstanding selection of gay bars and clubs that are generally located close to one another and offer a diverse range of nightlife experiences.

Boystown is easily reachable by any of the city’s public transport networks and the compactness of the district means that the area can be explored mainly on foot. Gay travelers in Boystown can expect a hate-free visit, with the area being known for a palpable liberal open-mindedness.

Gay pride in Chicago

Every June, the streets of Boystown become even busier as the district prepares for Pride Fest, an annual celebration of Chicago’s LGBT+ community and culture. Pride has been running in Chicago since 1971. The festival spans a weekend and regularly draws crowds of over 100,000 attendees. A range of street vendors, performers and LGBT+ organisations line the streets during the celebrations, and gay travelers can expect to enjoy performances from some of the world’s biggest DJs and singers.

The city also holds a pride march on the last Sunday of June, where thousands of LGBT+ people and allies walk the streets of Chicago in celebration of their identity and in demand of equality and fair treatment for all members of the LGBT+ community.


Gay rights in Chicago

Illinois has some of the most progressive LGBT+ rights laws in the United States, with gay residents and travelers alike being protected by anti-discrimination and anti-hate laws.

Marriage Equality was achieved in Chicago in 2014 and conversion therapy has been officially outlawed since 2016, meaning young LGBT+ people are protected from harmful pseudo-psychiatric practices.

Published: 22-Jul-2020 by George Pizani   |   Last Updated: 24-May-2022
On: Gay Chicago

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