Two-Day Towns: Chicago, IL

Minneapolis and Chicago have a funny relationship.

Chicago is, undeniably, an incredible city for food, culture, and architecture, and anyone in Minneapolis will be the first to say it.  But because it’s so close (an hour-long flight or a five-ish hour drive), the attitude is always “I can go to Chicago anytime; it’s just a short hop.”

Yet so few do.

Maybe Minneapolites are passive aggressively getting back at Chicagoans for not knowing that we’re just as great in all of those categories?  Who knows. All that aside, 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, 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.

View from Soho House roof

Where to Stay

Five years ago, we didn’t love the hotel options and often found ourselves in one of the same two that were in the higher price point category (The Waldorf Astoria, formerly the Elysian, or the Trump International Hotel & TowerYes, the name sparks controversy, but you can’t argue with the location and service).  And there’s always the Peninsula if you want more old-school luxury with a Michigan Avenue address, but stay north of the river if you still want to be on main and main—it’s close to the theaters and the Riverwalk, but just removed enough to give a little quiet and feel more neighborhood-y.

Today, there are more and more great options all the time, starting with our favorite: Soho House in the hot West Randolph/Fulton Market area. We also like the Langham across from the Trump for a higher-end experience in a supreme location. The new notables in town are the Virgin Hotel (by Virgin Atlantic) and the newly remodeled Chicago Athletic Association.

You’ll find all of the major chains, plus a smattering of boutique hotels, throughout the Loop and its surroundings—Kimpton’s got five downtown, which are all solid options, including a brand-new one (The Gray) opening this fall. A few other great boutique options include Public (complete with a Jean Georges restaurant with overly photographed lights) and the Thompson, which boasts Nico Osteria from the One Off Hospitality group of Avec and Publican fame.

Duck Duck Goat

What to Eat, Where to Drink

You’re going to eat—a LOT. Chicagoans are serious about their food.

Leave the Loop. Seriously. It’s packed with fast-service chains and touristy options (with some exceptions, including Good Stuff, the DC-based place flipping fat burgers and crispy fries worth fighting lunchtime lines).  The Purple Pig on Michigan started as a great find, but has now also become pretty touristy.

Instead, head west on Randolph to what’s become known as Restaurant Row (the neighborhood that Grant Aschatz and One Off Hospitality built), with heavy hitters including Stephanie Izard’s trio of goat-centric restaurants (hit Little Goat Diner and its attached bakery for breakfast or brunch, the new 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). 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).  Both are must do’s.

GS Smoked Meats 3
Cold Storage1

Rick Bayless has jumped on the Fulton Market bandwagon too, with his recently opened Lena Brava.  That makes this the area to hit some of the best in Chicago, from Grant Aschatz (Roister, Alinea, or the easier-to-get-in-and-try-for-a-drink Aviary) to Paul Kahan (Publican, Avec, Blackbird, PQM) to Stephanie Izard to Rick Bayless.

And, if that weren’t enough, there’s also Green Street Smoked Meats, one of the best for barbeque, and Swift & Sons/Cold Storage for an update to the classic steakhouse and oyster bar.

And, of course, the cheeseburger at Au Cheval isn’t to be missed. Go early or for brunch, and you can cut your wait from the peak three-hour line to a half-hour (get a latte at Little Goat’s coffee bar while you wait). Get a bar seat if you can, because watching the expediters and friendly, fast, tattoo’d cooks is truly fascinating. Afterwards, newly opened Federales is where the cool kids are drinking on a killer patio—forget the other patrons; even the staff might make you feel aesthetically inferior.

Big Star 2

If you have any time left after hitting this incredible neighborhood, here are a few other ’hoods you must stop by:

In Wicker Park, the tacos, the vibe, and the outdoor patio at Big Star are worth the hype (and, if weather allows, a genius takeout window helps combat the crowds—order your tacos and a horchata and eat at one of the best outdoor areas in town). A more elaborate Mexican menu can be found at Rick Bayless’ XOCO, or a more casual taco experience at Antique Taco.  Nearby urbanbelly brings a strong Korean fusion game (and passionfruit lemonade, the most refreshing afternoon drink in town). Dove’s Luncheonette is another clever addition from One Off/Paul Kahan that is classic diner look meets an interesting southern/Mexican menu that’s worth the wait.  For dessert, wander towards Jeni’s, the Columbus, OH-based ice-cream shop with creamy signature and seasonal flavors (sweet corn and black raspberry screams “summer”). Or to really indulge, walk a little farther to Mindy’s Hot Chocolate to finish out the night with a flight of hot chocolates or one of the almost-too-rich desserts that won Mindy Segal her James Beard award.

Last mention:  Violet Hour is not to be missed for cocktails, either before or after your indulgence begins.

In Logan Square, Longman & Eagle made Logan Square the place worthy of an Uber ride.  While you’re there, check out Giant, the new one by Jason Vincent (formerly of Nightwood),  and the classic Lula Café that came even before Longman & Eagle

And if you’re going to pack a riverside picnic or want to get lost inside for a few hours, stop by one of the food halls that are cropping up all over the city—the second location of Mario Batali’s Eataly in is in River North, and similarly concepted Latinicity brings all the Latin flavors to the Loop. Soon-to-open Revival food hall will boast 15 local food stalls, a reading corner, a bar, and a record store.

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