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Jay Michael

Founder, Flats Chicago

For our G&F Men’s Issue, we’re dishing with our favorite neighborhood know-it-all and real estate extraordinaire, Jay Michael. And, in case you haven’t dived into this issue, we even stole some time at a few of his properties for our current Men’s fashion story.

Jay is founder of FLATS Chicago, a property management company like no other. No. Seriously. Like none other that you’ve ever seen. Behind this housing brand that is slowly banishing the connotations of the word “landlord” and breathing new life on the Northside, Jay’s delicate eye to detail in every, well, detail is totally smart. His eye for damn good design has led to redeveloping over 1,000,000 square feet of space over the past 10 years. FLATS Chicago and Jay Michael want you to live well in a space with individuality and soul—how can we argue with that? Follow along as we chat with Jay in his ridiculously good looking apartment and frolic through Uptown at his all-time favorite hot spots.


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SPOTLIGHT_video link_Jay Michael Flats Chicago In the video interview above, Jay Michael lets us in on his biggest inspiration, and how the mammoth buildings of Uptown often have an even larger story behind them. We chat with him in his home—where he shows off his serious interior design chops—and learn more about how FLATS Chicago is slowly reinvigorating Uptown in all its glory.

We couldn’t wait to pick Jay’s brain on his go-to Uptown jaunts, so you bet your bottom we’re covering all the bases from antique shopping to happy hour to the ultimate scenic route. You can count on these hot spots to be vivacious, stylish and, like anything Jay puts his touch on, FUN.

SPOTLIGHT_map_Jay Michael Flats Chicago

 1. BROWNSTONE ANTIQUES, 5234 N. Clark Street, 773.878.9800
Jay says: This may feel like a total junk store but let me tell you, some of my best finds were acquired here. Get ready to dig.

2. BRIMFIELD, 5219 N. Clark Street, 773.271.3501
Jay says: Julie, the rummaging owner, scours the country looking for the most winter lodge meets summer camp type finds and reworks them to plaid perfection.

3. BAKER & NOSH, 1303 W. Wilson Avenue, 773.989.7393
Jay says: Baker and Nosh has my absolute favorite baked goods…their coffee is lovely but nothing compares to their gourmet sandwiches on fresh baked bread.    

4. HERITAGE OUTPOST, opening soon 
Jay says: My favorite Chicago coffee shop is Heritage Bicycles on Lincoln and thankfully they are opening their newest shop, Heritage Outpost, in the next few weeks at Wilson and Beacon

5. GREEN MILL, 4802 N. Broadway Street, 773.878.5552
Jay says: Chicago’s most iconic jazz bar is actually perfect for happy hour. No tourists and never a wait.

6. VINCENT, 1475 W. Balmoral Avenue, 773.334.7168
Jay says: Curried mussels, obscure yet approachable wines, the idilic venue lit by church candles and the perfect dinner menu. What’s not to love?

7. PHO 888, 1137 W. Argyle Street, 773.907.8838
Jay says: I love Vietnamese but this spot has my heart. Spring rolls, papaya salad and a bowl of pho. It’s Uptown’s best kept secret.  

8. TWEET, 5020 N. Sheridan Road, 773.728.5576
Jay says: Connected to my favorite, and the hairiest, gay bar in Uptown, Big Chicks (pictured above photo from Big Chick’s gallery), Tweet has delicious brunch on a diner budget. Try the daily quiche. You’ll never be disappointed.   

9. THE BLACK ENSEMBLE THEATRE, 4450 N. Clark Street, 773.769.4451
Jay says: I have only been to one musical that gave me chills and it was at the Black Ensemble Theatre. Think Dreams Girls meets Etta James (pictured above) in a beautiful new theatre.

10. MONTROSE BEACH
Jay says: Park your car at The Dock at Montrose Beach, 200 W. Montrose Drive, and take a walk south through the small but mighty nature preserve. It’s something you never thought existed in the city and has the best skyline view I have ever seen.

Find more at FlatsChicago.com + JayMichael.co

SPOTLIGHT_link to fashion_Jay Michael Flats Chicago
PHOTO BY TIMOTHY MUSHO
MAP ILLUSTRATION BY KATIE BUCKLEITNER