Flashback to 1990, I frequented a Portland record store called The Ooze, where I had a crush on the owner. She sold me an EP of a band called Too Much Joy, which led to a lifelong semi-obsession with the group. Especially because they’d stopped playing shows by the time I was old enough to travel to see them. More proof that I was born to late for the cool stuff.

Flashforward to September 2023, and I’m on my way to Chicago to see them for a second time, not just because I’m a superfan, but because they’re kinda friends now. Teenage me would have never believed I’d be so cool, but really, that’s the kind of guys they are. It was just a quick long weekend trip, I flew into O’Hare and took the train into downtown. At 9pm the ride is easy, cheap, and entertaining, but I bet it sucks at rush hour.

I checked into the HI Chicago Hostel, where I was sharing an 8-bed women’s dorm room. I got a side-eye reaction from one of the women when I entered the room, which is no big deal, but she’ll make an appearance later. I threw my stuff in a locker and hit the streets. I needed a burger and drinks to soak it up, and Miller’s Pub was just a few blocks away.

Miller’s Pub has been in Chicago in one form or another since 1934, but this particular location dates from the 70’s. Still, it’s adorned with lush wood and brass, old celebrity photos, and oil paintings that look close to a century old. A WSJ article from 2003 said, "At the bar the atmosphere is a bit like an episode from Cheers. Everybody but me knew the bartender's name and that he was about to go on vacation.... Miller's is my idea of unself-conscious perfection." Accurate. It was about 11pm on a Friday and the bar was full of people in suits celebrating another week of capitalism and the old timers at the bar silently enduring its legacy. As a solo traveler, there’s always room for one more at the bar, and its my favorite place to be anyway. The bartender was Tony and he really was about to go on vacation. I got a big juicy cheeseburger that was too much for me to handle, but I gave it my best shot. The music was alternative 80s deep cuts. Everyone was in a good mood and very chatty, I reveled in conversations of those who came and went from the bar until I nearly closed the place down. Miller’s somehow avoids the trappings of over-tourism, irony, or malaise that often plague landmark pubs and restaurants. I had a great time, it was a warm welcome to Chicago.

The next morning, the only other person in the dorm room was the side-eye woman from the night before. For some reason, she felt she needed to lecture me on the dangers of vaccines, how sunlight cures covid, and her various opinions on people from other countries and cultures which i won’t be repeating here. Seriously, lady? Did you really think a trans woman was going to take your side? So weird. Anyway, I needed coffee and food of some kind so I headed to Eleven City Diner, because any place that serves breakfast all day is a place I want to check out.

Eleven City Diner is an homage of sorts to classic diners and delis from the 1940s and 50s. Sure, it’s a bit kitschy, Disneyfied even, but it does what it does very well. My seat at the counter was front row to all the food whizzing by, the malts blended, and coffee pots brewed. The place was bustling with kinetic energy and everyone working there was friendly. My server approached and said, “Wait don’t tell me, you’d like water, coffee, and a mimosa, right?” I said that was amazing, how did he know that? For some reason, he thought I was a regular and that’s what I always got. The menu effortlessly moves from lox and bagels to Mexican scrambles and why not? The head chef is Mexican, most of the kitchen is of Mexican heritage, and American culture is absorbing more Mexican food and culture all the time. Or as owner Brad Rubin says, “A little spice never hurt anybody.” So putting Tapatio on my deli scramble seemed almost authentic. Breakfast was perfect, the corned beef and pastrami were delectable, the line out the door is justified. Arrive early if you want a table, otherwise deli items are available for takeaway at the counter.

As usual for me, I spent my time walking the city, getting lost, while eating and drinking along the way. One of my Must Do things to see was the top of the Sears/Willis Tower, my Ferris Bueller pilgrimage. There is a “Skydeck” on the 103rd floor, where you can step out onto clear platforms and vomit immediately. But I preferred to see the view from the Signature Bar on the 95th floor, it’s cheaper and you can stay as long as you like. Yet again, being a solo traveler put me right in the front seat, with a seat facing the window, watching the sun set over the city. After I got over my fear of heights and was able to sit comfortably, I could’ve sat there all day. If you’re patient and ask nicely, you can find a spot to put your forehead against the glass and relive the famous Cameron Frye moment. [UPDATE: Sadly, just days after visiting, the Signature Room and Bar suddenly closed its doors for good on Sept. 28, 2023.]

There are lots of sights to be seen just walking around the city and one discovery inevitably leads to another. Taking photos of the “Chicago” Theatre sign led me to the supposedly haunted Alley of Death, where 600 bodies had been piled high after the deadly fire at the Iroquois Theatre. Also nearby is the hands-on Museum of Medieval Torture, where you can enjoy turning the crank on The Rack or hoisting a blade of The Guillotine (there’s another one in the ladies’ room!). It’s cheesy fun, worth the discounted price I found online, and was made better by the edible I purchased at a dispensary. Get the audio tour, it adds a lot to the experience, edible or not.

I also stumbled upon the Palmer House, drawn in by pictures of its ballrooms from the street. The interior is not to be missed, even if just for a few minutes. They do serve food and drinks in the spacious, opulent lobby, a remnant of bygone days of extravagance. I asked for an Irish coffee and though the bar didn’t have coffee, the bartender graciously went to the cafe to get a cup of coffee then brought it back to make my drink. Oh yeah, it’s THAT level. Naturally, I spent the next 90 minutes exploring the hotels upper levels and amazingly didn’t get kicked out. The Palmer House has a fascinating history, dating back to the 1880’s in the first incarnation of the hotel. It’s been home to dignitaries, celebrities, performers, and of course, murder over the decades. Legend has it that the brownie, yes the delicious cake/cookie dessert, was invented here. They still sell the “original recipe” brownie and I tried it. I’m not weighing in on the debate of its origins, I’ll just say I didn’t care for it.

If you’ve been walking for a few days and just want to be shown around, I highly recommend an architectural boat tour. Even the locals will tell you it’s a great time and you’ll learn a lot. There are many to choose from, I went with a 90 minute tour by Wendella. Discounted tickets can be found on Viator, Groupon, and TripAdvisor. Once I figured out which dock the boat would be loading from, I shuffled onto the boat with everyone else. The top deck is all seating and it had filled up quickly, but rather than trying to squeeze in with the crowd, I went to the bar below deck. With a drink in hand, I was free to roam the boat and listen to the live spiel from the guide. For me, this was much better than sitting in the sun with a bunch of sweaty tourists. There were benches all over or I could stand right at the bow. During our trip, Joe, our guide, proved to be an endlessly captivating source of knowledge about the city and its rich history. I was constantly absorbing new information from him, and never once did he leave me feeling bored. Most interesting to me was that Chicago was actually built with 2 floors underground big enough that major roads and even Amtrak run right under the city. You could see the layers from the river!

After the cruise, I set out to see this underground for myself. From one of the many bridges crossing the river, I managed to find myself wandering around Lower Wacker. It’s a very busy street, with tendrils that lead to loading docks and dumpsters for the businesses above. GPS doesn’t penetrate down there so I very quickly got lost amongst the rats and pigeons. I emerged a couple of times in deep alleyways and my GPS put me nowhere near where I thought I’d be. But I was able to orient myself to a general idea of the direction I wanted to go and go back in. I was reasonably sure that somewhere down there I would find a bar. It’s just too cool to NOT have a bar, right?

Right! I didn’t know I had struck gold when I saw the sign for Billy Goat’s. All I knew was I really needed to pee and despite the “enter at your own risk” sign, I was going in. I immediate told the bartender, “I need to pee and I need whiskey, in that order.” “Ladies room, down the hall, on the left,” he instructed. When I returned to the bar, I took a seat at the corner, adjacent to a friendly looking guy. I ordered my whiskey and chatted up the guys, who were eager to tell me stories of the bar. It started to dawn on me, this is the famed “Cheezborger” restaurant featured on Saturday Night Live in 1978. Billy Goat’s has since expanded to many locations around Chicago, there’s even a location at Midway airport, but this is the original. I felt honored to be accepted by the regulars at the bar and regretted that I didn’t have more time to hang out. The man sitting next to me said something about “his boat” today and I realized I knew who this was. “You’re Joe! From the boat tour!” Yep, it was him, I had managed to stumble upon his after tour drinking spot. He’s a helluva nice guy and super knowledgeable about Chicago, you can even book a private tour with him at Tours By Joe.

By now you might be wondering about the Too Much Joy show that brought me to Chicago and likely brought you to my website. The show was at the Blue Island Beer Company, which is several miles south of Chicago. I had meant to take a train but couldn’t find the station so I took a taxi. Blue Island Brewery makes their beer on-site and serves it up in an unassuming taproom that hides a surprisingly expansive performance venue. They even canned a special TMJ brew just for the show! I was going to save the can as a souvenir but I couldn’t resist drinking Too Much Joy beer with Too Much Joy. The boys put on a fantastic show and it was even a reunion of sorts - they were joined onstage by Sally Timms and Jon Langford of The Mekons! AND it was Bill Whitman’s birthday! I had a blast singing along with my favorite songs, meeting other fans, and hanging with the band. Definitely worth traveling 2000 miles for. If you’re a fan, you MUST make the journey to see them if you get the chance. And buy their new albums!

I really enjoyed my visit to Chicago, it’s a vibrant city with lots going on and has a much different feel than New York or Los Angeles. You won’t be bored, that’s for sure, you’ll stumble upon so many cool things just by walking around. Like the Dave Matthew’s Bridge, which I’ll let you look up yourself. Everyone was very friendly with me but I did have one negative experience worth mentioning. I had been enjoying watching the Crown Fountain in Millennium Park when I put in my earphones and got up to leave. I heard a man shout angrily behind me, “Are you one of those perverts? Because you look like one of those perverts!” I kept walking but scanned the faces around me for allies. Their expressions confirmed that I was the target of his ire but, fortunately, they looked ready to support me. I ignored him and nothing came of it but it was startling.

I won’t judge the entire city because of one asshole with a southern accent. I believe Chicago is a safe place for queers and you should definitely visit. Go with a plan, it’s easy to get distracted with so many things to do, delicious food, and world class entertainment. I hope your experience will also be filled with Too Much Joy.

Are you a queer person in Chicago? What have your experiences been? Comment below!