A Guided Tour of Chicago with DJ Chrissy


We travel to Chicago to the location of DJ/Producer, Chrissy. He takes us around his particular places, as our My City guides continues across the pond.

Read more of our city guides

The biggest city in the Mid-West is famous for a lot of things, such as Chicago’s O’Hare International being the busiest airport in the world. It is also known for being a home to some of the most creative music movements and artists within the soul, blues and jazz scene, as well as being the city of some of the most iconic sports teams in North America. But maybe the most infamous reason why you’ll know the city, Chicago is where that clever kid Kevin out smarted Harry and Marv when he was “Home Alone” – a real success story.

Jokes aside, with a wealth of historical and industrial inspiration, Chrissy has a great setting to want to be able to carry on delivering a great sound. Described as ‘the hardest-working motherfu*ker in Chicago’, Chrissy is a genre-blending DJ, and a resident DJ at Chicago club Smart Bar. Not only does he co-run his own label Nite Owl Diner, but he also helped introduce the world to footwork music, and runs a successful juke/footwork label Loose Squares. We asked him for his best hangouts, and his insights of his home town of Chicago.

Stay up-to-date with all of Chrissy’s activities Soundcloud | Facebook | Twitter | Website

 Where’s the best place for a first date?

If you’re trying to have a romantic stroll, I think our parks are among the world’s best. Millenium Park and the Art Institute of Chicago make a GREAT date, and Lincoln Park and Humboldt Park are also gorgeous places to spend a couple of hours. But if you’re just looking for a public space to get a read on some complete stranger from Tinder, then take them to eat at Sultan’s Market: it’s dirt cheap but it’s also delicious enough that you won’t seem like you were just trying to take them somewhere cheap.

crown fountain Millenium Park
Photo Credit: Loop Chicago

Where’s your preferred place to chill and clear your head?

Again: we have top notch parks. But we also have a TON of amazing coffee shops–Intelligentsia, Julius Meinl, Wormhole, Gaslight, La Colombe, Ipsento, New Wave, Metropolis…

Ipsento Chicago Chrissy
Photo Credit: octopusgourmet

Where serves the best breakfast?

Chicago has a wealth of great brunch options; M Henry, Bongo Room, Dusek’s, Southport Grocery, and a ton of others. But if you want to avoid “brunchy” people and hour waits, go to Bang Bang Pie & Biscuits.

M-henry Chicago
Photo Credit: chicago.eater.

Where’s your favourite place to have a quiet drink?

Chicago isn’t really a “quiet drink” kind of town, in my experience. But Hopleaf has a ton of beers and a little bit more chilled-out of a vibe.

Hopleaf Bar Chicago
Photo Credit; pbase

How are you dressing for that quiet drink?

mens outfit grid quiet drink bar
SHOP: Edwin Memphis Shirt | Carhartt WIP Johnson Pant | Publish x Timberland Chelsea Boot

Where’s your favourite place to have a messier night?

Smart Bar, hands down. Great staff, cool atmosphere, and the best music programming in America. Full disclosure: I’m a resident DJ there so I am totally biased.

Chrissy chicago smart bar
Photo Credit: Resident Advisor

How would you describe your city’s style?

Chicago is the friendliest big city on earth, and we are very welcoming and down-to-earth, but we also looooove to throw shade at people for not being as welcoming or friendly or down-to-earth as us.

Where are your favourite places to shop?

There’s a lot of touristy shopping on Michigan Avenue, and then a ton of neat boutiques and local businesses in Wicker Park, Logan Square, Lakeview, Boystown…

Michigan Avenue Chicago
Photo credit: 10 Best

What song sums up your city?

Joe Smooth – “Promised Land” kind of sums us up: house music, happiness, and optimism despite some serious social problems.

Free Download Travel Guide Ebook


Written By