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Pride Journey: Chicago

Chicago beach and skyline

Chicago Pride might have been canceled but from Market Days, Boystown, Splash, to a gay beach, Joey Amato finds the Windy City still offers plenty of queer action.

Chicago is my kind of town…it really is. I’ve been to Chicago more times than I can count over the years, however I have never written a Pride Journeys article about the city. Well, it’s about time I did!

Joey Amato at Chicago's Bean

The author, Joey Amato, in front of Chicago's Bean sculpture. 

I planned my visit to the Windy City to coincide with Market Days, one of the city’s premier LGTBQ+ festivals. Since relocating to Nashville and then Indy, I had heard dozens of stories about this event from friends from around the country who would travel to Chicago specifically to attend. This year’s festival was going to be iconic since last year’s event was cancelled due to the pandemic.

Trixie Mattel, Todrick, Hall, and Greyson Chance were among the headliners performing this year, however I was most excited about seeing Lisa Lisa, Jody Watley and Ty Herndon.

Tyler and I arrived on the first day of the festival and it appeared to be similar to a pride event. Vendors lined the street selling everything from artwork to sunglasses as well as some other more risqué items. It didn’t take long for us to run into a few friends, some of which I hadn’t seen in many years. Market Days is what you make it. You can spend the afternoon strolling Halsted Street or you can skip the street fair and head straight to the bars, clubs, and circuit events in the evening.

Ty Herndon at Chicago Market DaysTy Herndon at Chicago's Market Days


Take some time the next morning to check out the hotel’s 2-story art gallery space or maybe find time for a quick workout in their fitness center before heading to Hutch American Bistro for brunch.

Hutch is located off the same red line stop as Boystown so it’s quite convenient. I ordered the smoked salmon avocado toast which came with fruit salad. It was light yet filling and the perfect way to begin the day. We went back to Hutch for happy hour of a different day and sampled a few additional items including the guacamole + queso and Chicago meatballs. The restaurant offers a daily happy hour menu consisting of half-off select appetizers as well as $3 champagne. Yes, please!

When in Chicago, you would be remiss if you didn’t visit one of the city’s numerous cultural institutions. Since the Field Museum and Shedd Aquarium are in the same complex, we decided to visit both in the same morning.

Tyler and I are both huge animal lovers, so we headed straight to the beluga whale and penguin habitats. Beluga whales are one of my favorite mammals, so it was wonderful to see them up close.

Sue T-Rex at Field MuseumSue, the largest and most complete T-Rex skeleton was recently declared nonbinary.


The Field Museum is home to one of the largest (and best in my opinion) dinosaur exhibitions in the country. The chronological display brings guests through history and mass extinctions leading up to the birth of dinosaurs. The Field Museum is also home to Sue, the largest and most complete T-Rex skeleton ever discovered. This is a must-see for any dinosaur lover. [Plus, a few years ago, Sue became the first nonbinary dinosaur, with the museum using they/them pronouns.]

After a fun filled day of partying, head back to the 21c Museum Hotel located in the River North neighborhood, about a 25-minute red-line commute from Boystown. The boutique property is one of the newer hotels in the 21c family. I’ve stayed at their properties in Oklahoma City, Nashville and Kansas City and they never disappoint. The 21c Chicago was kind enough to provide me with a wonderful corner suite as well as their Love is Love package, which included a pride tank top, perfect to wear during the festivities.

We decided to walk back to our hotel after visiting the museum as the weather was perfect for a leisurely stroll along the lake – until it started raining. With nowhere to take cover, we just admired the beauty of Chicago’s architectural wonders as well as the sculptures in Millennium Park including the world-famous Bean.

Speaking of walking, the city offers free walking tours through Chicago Greeter. Local guides volunteer their time to take guests on customized walking tours of the city. We decided to focus our tour on architecture and landmarks. Our knowledgeable guide took us to some places we would have never known about if we had set out on our own. While we took a journey through the North Loop, the Greeter Tour service can take visitors through many of the 77 neighborhoods in the Chicago area.

Before heading back to Boystown, grab a quick bite at Tied House. I was thoroughly impressed by both the food and service of this establishment. Tyler and I shared a few items including the Black Bean Hummus prepared with salsa roja and lime crema as well as the Watermelon & Bigeye Tuna which came with pickled ginger and a koji vinaigrette. The Short Rib Risotto was served with roasted sweet corn Risotto, cherry tomato, summer squash. While the short rib portion was a bit fatty for my liking, I found the risotto part to be incredibly flavorful and cooked to perfection. I would order the risotto by itself next time…it was so good!

Boystown of course is the heart of Chicago’s LGBTQ community. There are dozens of shops, restaurants, businesses, and nightlife venues catering to every gay under the sun. Some of my favorites include SidetrackHydrate NightclubSplash and Progress Bar.

What many tourists don’t know is that Chicago has a gay beach. While it may not have the waves of Fort Lauderdale, Hollywood Beach attracts some of the most beautiful people in the Midwest and is only about a 10-minute Uber ride from Boystown. With only a few months of beach weather per year, locals flock to Hollywood Beach every opportunity possible to soak up the sun.

There is way too much to see in Chicago to fit everything into a weekend. Especially when you include a festival as well. I am going to make an effort to visit more frequently, especially since it’s so close to my home in Indianapolis.



Joey Amato is a travel writer and publisher of Pride Journeys.  

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