Fleetwood Max

A Cadillac of a South Loop Hangout

None 8 Photos Fleetwood
We don’t know what’s keeping you warm right now.

Maybe you’re drinking a mug of hot cocoa. Maybe you’re sitting in a hot tub. Maybe you’re sitting in a hot tub that’s filled with hot cocoa.

The point is: stay put. Snuggle. And rest assured that soon you’ll be rewarded with a bounty of lobster ravioli and some old-school Motown.

Get ready for Fleetwood, a revved-up little date spot in the South Loop, now open on weekends only.

Fleetwood. As in the Cadillac, not the Mac. See, if you wanted a fully loaded Caddy back in the day, you’d find yourself around here. Now, however, you’ll drop by when you and a date want to test-drive a few cheeseburger sliders.

Start with a classic martini at the bar in the back, and then find a spot on a leather settee. The comfort-food menu is designed to share—pan pizza, calamari, prosciutto-wrapped shrimp—so bring someone share-worthy.

Like its namesake, this place doesn’t exactly shy away from flamboyance. Plum-colored walls, glass chandeliers, a few faux-fur throws, purple shag carpets, a little Barry White playing overhead...

But sorry, no fuzzy dice.


2333 S Michigan Ave
(between 23rd and 24th)
Chicago, IL, 60616


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