The first time I visited Chicago was 2012 in my late 20s as a restaurant publicist. Armed with an extremely exhaustive Excel spreadsheet heavily cross-referenced with anything Anthony Bourdain ever said about Chicago and all the Adam Rappport*-era Bon Appetit coverage I could bookmark, I pitched a three-day friends getaway packed with warm beers at a turtle racing bar, dinner at Girl & the Goat, madhatter-esque cocktails at The Aviary, and late-night insults & hot dogs at The Wiener’s Circle. We took touristy pics in front of Wrigley Field, ate the obligatory deep dish pizza, and even managed to sneak in a spin class at the not-yet-open-in-Boston-and-therefore-very-cool Flywheel (RIP). To top it off, we stayed at the Four Seasons on a friends & family rate thanks to a colleague who used to work in Four Seasons PR. Charmed by the Four Seasons Martini Man room service perk and the single-use bathing suits the spa gave us so we could hit the pool, our stint at the Four Seasons was the cherry on top of an epic Chicago weekend.
I’ve since returned to Chicago several times to visit friends, and each time I get frustrated that I run out of time to visit the 20+ places I want to visit on my ever-growing list. Every year, a flock of new bars & restaurants in Chicago religiously makes the “best of” lists nationally and internationally. My tastes are no longer driven exclusively by traditional food media (and the idea of sitting through a 4+ hour tasting menu makes me want to gouge out my eyeballs), but these lists do tempt me nevertheless.
Here’s a mix of my favorite Chicago spots, as well as some new ones I plan to check out on my next trip.
Gus’ Sip & Dip: A simple concept for a bar: martinis and dipped sandwiches.
312 Fish Market: Sushi counter with a few tables inside a food court/supermarket.
Rick Bayless: Despite visiting Chicago 5+ times, I’ve never eaten at a Rick Bayless restaurant (I’m not counting the Frontera Grill at O’Hare, even though it was pretty good). Next time, I’ll try to hit one of the more casual spots like Xoco or Bar Sotano.
Richard’s Bar: Indoor smoking has been banned for years, but that doesn’t stop anyone from lighting up inside. After a night at Richard’s, my friends and I dubbed Chicago the Vegas of the Midwest.
All Together Now: An accidental find on my last visit since this spot is around the corner from my friend’s condo, All Together Now is an all-day wine & snack bar with a shop attached. The menu design is quirky & cool and the Vanderpump-Rules-coded fried goat cheese curds are insanely delicious.
Il Carciofo: Roman pasta and pizza in Fulton Market from Joe Flamm who also has Croatian-inspired Rose Mary, which sounds very interesting.
Sharpies: Detroit-style pizza in the heart of deep dish land.
Birrieria Zaragoza: Birria at 8am when you land at Midway? Sold.
*He’s been canceled since then, I know.
