Cheers to Chicago, with photographer Paul Octavious

Chicago is like a city in an old cartoon where they show a big metropolis with a train going around it. It’s the ‘L’, our elevated train system that connects the north, south and west sides of the city. You can see the trains crossing and crossing the streets – it’s just surreal. I’ve been here since 2007, a year after landing my first job as a photographer. Before that, I barely knew what the Midwest was — I had never really been through Connecticut, where I grew up. Today it’s my home: I have a son here and my parents moved to town. The Midwest has been charming and welcoming.

Chicago Athletic Association Hotel near Millennium Park

Uptown, the neighborhood I’ve always lived in, has changed a lot since I arrived. It used to be Chicago’s entertainment district, so it has all the old theaters, the largest of which is currently being restored. We also have amazing beaches: I live four blocks from what looks like an ocean, but it’s actually Lake Michigan.

Paul Octavious on Chicago Cricket Hill

Paul Octavious on Chicago’s Cricket Hill © Kevin Serna

Coming from New England, I love green spaces, and Cricket Hill, one of the only hills in town, is just down the street. It was built in 1948 to accommodate our beaches: they took soil from a nearby construction site and turned it into a perfect green mound. Richard Daley, the mayor of Chicago at the time, was supposed to have said, “Any good city needs a good hill. And that was it! He inspired my series of photographs Same hill, different day, where the inhabitants are like actors, the hill is a stage, and I watch it change every day. I’ve been documenting it for about 14 years now.

The Garfield Park Conservatory
Garfield Park Conservatory © John Gress/Corbis/Getty Images

During the colder months – which can be very unpleasant – I get my dopamine fix at the Garfield Park Conservatory, a giant greenhouse built in the early 1900s. In the winter, it’s like one of the only places you can warm up, stroll through greenery and smell the moss.

Chicago isn’t known for its fashion as much as some other places, but we’re getting there. My favorite store is Notre, which opened in Andersonville – what we call our “Swedish gay neighborhood” – and sold clothes that nobody else really had: independent designers like Craig Green, Reese Cooper and Wales Bonner . Now he’s based in a beautiful boutique in the West Loop that’s made entirely of common Chicago bricks, the historic clay bricks we started making after the Chicago fire of 1871. On the shopping side, I also like Merz Apothecary, a pharmacy that might prescribe you tangerine oil for a mild cold and stocks some amazing perfumes and candles.

Our, Octavious's favorite shop
Our, Octavious’s favorite store

It’s kind of stupid how good the food is here. For special occasions, I like Cherry Circle Room, the restaurant at the Chicago Athletic Association, a beautiful hotel near Millennium Park. It was once a men’s sports club and the current owners have created something reminiscent of the look of its 1890s heyday; I go with my dad and order steak, gravy and bubbles. Recently, I also ate at Kasama, where my supper club held an event. It’s a Michelin star Filipino restaurant in West Town, which is cool because my son’s mom is Filipina.

Chicago Athletic Association
Chicago Athletic Association

If you can handle the trip, Calumet Fisheries, a little shack on 95th Street, serves up some of the best smoked fish I’ve ever eaten; my favorite is the pepper and garlic salmon. Old Fashioned Donuts, another South Side institution, is a 15-minute drive away. The owner is now 83 and you can see him in the window making his simple glazed donuts. They are so good – but again, you really have to work at it.

Broadway Green Mill

The Green Mill on Broadway © Kevin Serna

I’m always on the lookout for the perfect Alaska, a Martini made with gin and yellow Chartreuse. The best I’ve had so far has been at Lula Cafe, one of the many bars in Logan Square. When I go out, I like to sit next to people – not across from them – and Lula Cafe has a great “sit next to me” vibe. Back in Uptown, another great spot is the Green Mill, a jazz club that’s been around since the days of Al Capone. Going there is like being transported back to the 1920s: it’s wild, it’s beautiful and it’s one of my favorite places here.

Chicago nightlife, especially queer nightlife, is amazing. The Green Mill plays jazz until two in the morning, and we also have two big dance nights: Slo ‘Mo at the Sleeping Village plays R&B and sweet jams, while Queen is every Sunday at the Smartbar. The city is known for its house music, and Smartbar is a place where house music is glorified. Drag queens come here and club kids come here. They peek, walk around and introduce themselves and show themselves.

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