Travel Thursday: Gay Guide To Summer (Yes!) In Chicago


Ah, Chicago. It's no surprise that a place known for stuffing as much as possible between two buns is also one of the best gay cities in America. Liberal attitudes, hot boys, famously friendly people, world-renowned restaurants, spectacular urban beach, and all the amenities that a city with 2.7 million residents has to offer await you in this veritable Midwest man fest. And no place - in the opinion of this biased but Midwesternly humbled Chicagoan - shines in the summertime quite like Chicago.

While for some of us summer might seem worlds away, now is actually a perfect time to start thinking about your summer Chicago trip (not to mention to unthaw with some warm weather mental escapism) and you can find everything you need to about planning your trip to the Windy City right here.



The Boystown is Mine

Chicag-oh no she betta don't! Boystown is the gay hub of Chicago and the first official gay district in America. Things have only gotten gayer over time, and any RuPaul's Drag Race fan knows that some of the greats (Kim Chi, Naomi Smalls, and Shea Coulee) - and not so greats (Laila McQueen) (Seriously JK! Nothing but love) call Chicago home. 

The huge, multi-room bar Sidetracks is all but the official watering hole of Midwestern homosexuals, and is THE meetup spot to down cheap vodka waters before heading to your club of choice. 

Berlin is my personal favorite dance spot in Chicago / the universe and features an eclectic roster of performers ranging from drag queens to cosplayers - all of whom generally bask in the limelight until at least twelve o'clock. After that it's up to you to create your own spectacle on the dance floor with the help of highly danceable house music blaring until 4 A.M. Berlin is conveniently a cash-only bar, so come prepared. Check out for the performance schedule.

You can also stop by the noisy, crowded, and always-fun shoebox-sized hot (literally) spot Scarlet Bar, and just a couple doors down you'll find top 40 fare on the crowded Roscoe's Tavern dance floor. The people here pile up on the earlier side, so it's a great spot to get in some early bird twerking if your overworked self wants to be in bed at a reasonable hour. Fair warning: This is the bar where you are most likely to see Midwestern bachelorettes. But at least they're very glamorous.

If you're feeling more on the chill side, you can relax with drinks and dudes at Kit Kat Lounge and Supper Club. Sip creative martinis and view occasional drag performances in the adorable dining room.  


Beach Please   

The Lake Michigan beaches dotting Chicago's shoreline are truly the gems of the city in the summertime. Thanks to the foresight of one of Chicago's biggest advocates, Daniel Burnham, the entire lakefront running the length of the city must remain accessible to the public until the end of time. Or until Trump turns it into a golf course / sex club. But for now it stays, and traversing the bustling 18-mile long bike trail winding its way along the lake is an excellent way to explore the beaches that feature white sand and sparkling blue water. Like ocean beaches. But without the salt. And the underwater animals that eat people.

Kathy Osterman Beach

Also known as Hollywood Beach, this is Chicago's gay beach - a designation made perfectly and proudly clear by the rainbow flag-plastered break wall. Gaggles of gays show off their hard work at the gym in barely-there Speedos, providing enough eye candy to give you a cavity. Although alcohol is not permitted on Chicago beaches - and you very may well get a ticket for flashing a beer bottle - I've never had the authorities question my "water bottle" aka the "source of my alcoholism."  



Oak Street Beach

This is my absolute jam in the summer, and odds are that on a nice day you'll find me sprawled out with my hub and pug in between dipping into the refreshing water. Oak Street Beach encompasses both a sand beach as well as what I endearingly refer to as the "concrete beach." The latter is obviously a sand-in-your-crannies-free experience and allows you to jump right into the deep water. Both spots include breathtaking views of the Hancock Tower, and in addition to the option of refueling at the Oak Street Grill, downtown and its hundreds of restaurants are directly across Lake Shore Drive from the beach.



North Avenue Beach

Remember how I warned about Midwestern Bachelorette parties? North Avenue Beach is like a bachelorette party mixed with every bachelor party ever mixed with every frat house ever, and while it's not my cup of teabags, if you're Snookie, you will probably feel right at home. The blaring music from a dozen different speakers is a downside, but the hundreds of hot shirtless straight guys might just make North Avenue worthy of a pit stop if the thirst is real for you.


Put It In Your Mouth

Chicago is one of only four cities in America with Michelin Star-rated restaurants, and I highly highly recommend that you take advantage of the buzzing food scene while visiting. The best restaurants can be booked out months in advance on weekend evenings, so make sure to make reservations early so you can sashay past the people waiting with a bitchy look on your face. Like... someone I know does. Me. I do that. 

Many of the most buzz-worthy Chicago restaurants are in the West Loop - more specifically Randolph Street, also called "Restaurant Row." This is where you'll find my new personal favorite spot - Chef Grant Achatz's smash hit restaurant Roister - as well as the ultimate restaurant scene staple The Girl and the Goat and the cocktail lounge to end all cocktail lounges - The Aviary. Here you can expect drinks so Instagram-worthy that your deluge of double taps will more than make up for the hefty bill. 

If you want to impress your friends, make a reservation at Restaurant Row's subterranean sushi spot Booze Box. Securing a seat at one of the limited booths surrounding the crowded bar is as easy as making an online reservation, and yet later on in the evening you'll receive enough jealous looks from pleb standers to make you feel like Beyoncé.  

The gorgeously-renovated neo-gothic treasure the Chicago Athletic Association will take you out of the West Loop, and can be found directly across Michigan Avenue from the famed "The Bean." Ogle the architectural detailing as you head to the back of the second story to dine at the delish Cherry Circle Room. Then take the elevator from the ground floor up to the rooftop bar Cindy's to cap off the evening with truly breathtaking city views.




Northalsted Market Days is a uniquely Chicago tradition, and is the largest gay event in the city and the largest street fair in the Midwest, period. This year's Market Days will take place from August 11th - 12th. Expect to be surrounded by 300,000 of your closest gay shuffling along the bustling thoroughfare while taking in music and performances from five stages. Read more about Market Days on their website

This year's gay pride parade will be on June 24th, while Gay Pride Fest will take place June 16th-17th. While Boystown is always gay, it's like, super duper gay during Pride, and if you have a chance to visit at this time, you will not be disappointed. 

At Art Expo Chicago (September 27th - 30th) you will find much of the same gallery representation as art fair juggernauts like Art Basil Miami. The event will take you out to the tip of Navy Pier, and while you may not be able to afford some of the art, you can definitely afford the wine you can drink while pretending like you can. 


The stunning Frank Gehry-designed Pritzker Pavilion situated in Millennium park offers free concerts throughout the summer, and being slrawled out on the grass, surrounded by Chicago's famed architecture, while listening to music should be on every human's bucket list. The tunes varies widely - from established indie acts to classical music to rock - so make sure to check the schedules (not yet updated for 2018) if you're a picky listener. Find them HERE and HERE. Oh, and you can bring your own booze!


Well boys, If you do any combination of the thing above you will be partaking in what I truly think is the ultimate Chicago summer, but this isn't even to mention our world-class museums, parks, shopping, and more. If you live in or have visited Chicago and have some advice for travelers, please let us know in the comments below, or contact me on Instagram with any and all questions. And most importantly, have a gay ol' time in Chicago! 


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