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A gay guide to Chicago and Illinois

From city slicking to rustic Midwest adventure, Illinois has it all.

By Will Stroude


Road trips down a historic highway. Fabulous nightlife. Cosy countryside retreats. Whatever makes for an amazing holiday, you’ll find it in Illinois — a destination that’s amazing for all. Start your trip in Chicago, the large, shimmering city on the shores of Lake Michigan.

In the summer, city life meets beach life thanks to Chicago’s 26 miles of publicly owned beaches. Locals lounge on the sand, swim in the lake and play volleyball by the water, or just jog and bike on the public trails. Frequented by the LGBTQ community, the beach popularly called “Hollywood Beach” is officially named Kathy Osterman Beach, in honor of a Chicago politician who fought for gay rights in the 1980s.

Beyond the fun in the sun, Chicago’s spectacular skyline invites you to explore a city filled with world-class activities and attractions. Head to Millennium Park to catch a glimpse of Cloud Gate — aka The Bean. Or hop aboard a tour boat to cruise along the river and learn about the architecture that tells the history of Chicago in every brick.

Couples soak up the sunshine in Chicago’s Millennium Park

The metropolis of downtown Chicago may be exciting, but it’s the diverse neighborhoods that lend the city its character. Head into any of the pedestrian-friendly neighborhoods, such as Andersonville, one of Chicago’s largest gay and lesbian communities, whose charming boutiques make it a popular weekend destination for locals and tourists alike. Quirky shops such as Foursided and Andersonville Galleria stock handcrafted gifts to give your shopping trips that personal, local touch.

When the sun goes down, Chicago comes alive. Friendly gay bars such as Progress Bar and Roscoe’s populate the stretch of North Halsted Street known as Boystown, a vibrant neighborhood that’s home to some of the best nightlife in the city. When it’s not hosting dance parties with throwback theme nights, Berlin is where you’ll find some of the neighborhood’s most entertaining drag shows.

The historic town of Galena, Illinois is the perfect place for a romantic getaway

Boystown is also the setting for two of the biggest events of the Chicago summer. Every year, nearly 200,000 visitors line North Halsted Street for Northalsted Market Days, the largest outdoor street festival in the Midwest. In June, the Chicago Pride Festival draws nearly a million revelers over a span of two weekends, culminating in a colorful Pride Parade, which is celebrating its 50th year in 2019.

Chicago is just the beginning of your adventure in Illinois. Nestled in northwest Illinois on the banks of the Mississippi River, the historic town of Galena is great place for a romantic getaway. Start with a stroll along winding Main Street, where restored red brick buildings house shops, art galleries and restaurants. Get a taste of Illinois wine with a visit to Galena Cellars Vineyard & Winery. And tuck in for the night at one of Galena’s many bed and breakfasts that dot the hillsides surrounding the town, such as the rustic Inn at Irish Hollow

Whether it’s a night on the town or a cosy night in, Illinois is full of LGBTQ-friendly destinations. There you’ll find a variety of warm, welcoming places to make your holiday amazing.

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