Exploring the Best of Chicago

January 20, 2018

Chicago is a first-tier US city with a food scene that’s exploded over the past fifteen years to rival New York’s (although in a completely different way, emphasizing the hearty over the spectacle—with the exception of Alinea’s showstopping dinner service and the Aviary’s cocktails, a production in itself). Sure, it’s cold in the winter, and it is actually windy—but there’s still plenty to do to fill up a couple of days, and the summers are nothing short of spectacular.

Soho House

Where to Stay

High-price standbys: The Waldorf Astoria, formerly the Elysian, is a big-dog go-to. And there’s always the Peninsula if you want more old-school luxury with a Michigan Avenue address.

Boutique options:

New notables:

  • The Ace Chicago (as cool-kid as the rest of the Ace hotels, but a great West Loop location)
  • Hotel Zachary (very new, farther north in Wrigleyville for baseball fans, but with decent dining options onsite)
  • The Hotel at Midtown (another athletic-club-based spot, at the intersection of a few good neighborhoods)

What to Eat, Where to Drink

You’re going to eat—a LOT. Chicagoans are serious about their food. It makes sense to organize by neighborhood, because once you get where you’re going, walking is easy—but the good restaurants are in clusters.

The Loop

Good Stuff
Leave the Loop. It’s packed with fast-service chains and touristy options, with a couple of exceptions if you have meetings or sights in the area:

  • For fat burgers and crispy fries: Good Stuff is worth fighting lunchtime lines
  • A good Michigan Ave pick: The Purple Pig (although it’s gotten touristy)
  • A worth-it food hall: Revival Food Hall puts a bunch of the city’s powerhouses in one place.

The West Loop/Restaurant Row

Duck Duck Goat

  • For your Stephanie Izard fix: Her trio of restaurants is all in this ’hood (hit Little Goat Diner and its attached bakery for breakfast or brunch, the newer Duck Duck Goat for “reasonably authentic Chinese food” in a kitschy-cool space, and snag a bar seat at Girl and the Goat come dinnertime—worth any wait).
  • For Asian fusion flavors: Bill Kim’s urbanbelly has been relocated (full disclosure, by Shea) next door to BellyQ, which takes Korean BBQ to new heights (cook your own or leave it to the pros).
  • For the Rick Bayless experience: The chef who brought Mexico to the Midwest has jumped on the Fulton Market bandwagon too, with his recently opened Lena Brava.
  • Because you have to experience it: Grant Aschatz is Chicago’s culinary master, if you can make it through the courses (Roister, Alinea, or the easier-to-get-in-and-try-for-a-drink Aviary).
  • The man who runs this town: Paul Kahan is a never-ending restaurant machine—try one or all (Publican, Avec, Blackbird, PQM).
  • Where the pasta is really good: Monteverde can’t be missed.
  • The best for BBQ: Green Street Smoked Meats

Cold Storage1

  • Taking steak and oysters to new heights: Swift & Sons/Cold Storage is a great update on the classics.
  • Go early: The cheeseburger at Au Cheval isn’t to be missed, but even our bar-sitting skills mean an hour wait at peak times. But watching the expediters and friendly, fast, tattoo’d cooks is truly fascinating.
  • For terrace envy: Aba is new, Mediterranean, and stunning.
  • Where the cool kids are drinking: Federales has a great patio—but even the staff might make you feel aesthetically inferior.

Big Star 2

Wicker Park

  • Worth the hype: The tacos, vibes, and outdoor space at Big Star are ideal.
  • Diner done better: Dove’s Luncheonette is another clever addition from One Off/Paul Kahan (surprise, surprise) with a classic diner look and an interesting southern/Mexican menu.


  • For dessert: Wander towards Jeni’s, the Columbus, OH-based ice-cream shop with creamy signature and seasonal flavors. Or to really indulge, go a little farther to Mindy’s Hot Chocolate to finish out the night with something that won Mindy Segal her James Beard award.
  • To feel like part of the ’hood: Etta, from the chef at acclaimed Maple & Ash, is warm and bright.
  • A lighter take on Chicago-style pizza: Pequod’s is technically pan pizza, but a little less doughy/heavy than deep dish—and has a better local following (the best sign).
  • For street food sitting down: Mott Street does modern spins on Asian.
  • Before or after: Violet Hour is not to be missed for cocktails.

Au ChevalCold Storage 3

Logan Square

  • Made the neighborhood: Longman & Eagle made Logan Square the place worthy of an Uber ride.
  • For bold flavor: Giant is newer and great.
  • Came first: Lula Café came even before Longman & Eagle and is great for brunch.
  • Biscuits. That’s It: You’ve gotta love a place like the fast-rising newcomer Bang Bang, where pie and biscuits are what’s on the menu.
  • For a rooftop: BiXi Beer is brand-new, the first Asian brewpub in town.

Farther North

  • For Michelin stars that aren’t as stuffy: Band of Bohemia in Avondale is the first Michelin-starred brewpub.
  • Good luck getting in: Also in Avondale, Parachute is worth the effort for Korean-American dishes.
  • For new and buzzy: Tied House in Lake View, from a Beard-winning chef, is sophisticated comfort food with a great outdoor space.

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