The Chicago Guide


Fresh off the heels of our Chicago goop pop, we can’t seem to shake the feeling that Chi town is our spirit city. In the two weeks we were lucky to call the Waldorf Astoria our home-away-from home, we’ve explored countless boutiques, bars, bakeries, and eateries, taking note of the ones that made our hearts skip a beat along the way. And while some may still see Chicago as the Second City, as evidenced by the deep list of restaurants we’ve amassed, the ever-expanding food scene is second to none.

Eli’s Cheesecake

6701 W. Forest Preserve Dr., Dunning | 800.354.2253

This is where real Chicagoans go for Chicago-style cheesecake—less dense than NY-style with a moist, butter-cookie crust. There’s a miles-long list of inventive flavors—white chocolate raspberry, hot chocolate, blackberry sour cream—but the original is still tops. Coincidentally, Eli’s is also famous for having the best tofu-based vegan cheesecake in the country, which according to lore, the owners developed after GP suggested there was a hole in the market for vegan cheesecake that didn't taste like cardboard.

Eataly Chicago

The Shops at North Bridge, 43 E. Ohio St., Magnificent Mile | 312.521.8700

Just like the NYC outpost, and the dozen or so locations all over Italy (as well as recent offshoots in Japan, Dubai, and Istanbul)—Eataly Chicago is a foodie wonderland. The sprawling space is packed with imported sauces, beers, sweets, and so much more. There’s even a selection of housewares and books. Stalls offering house-made breads, pastas, and cheeses are scattered throughout—we recommend doing a lap to get the lay of the land first before committing to any one spot. For more formal dining there are several restaurants that are pretty efficient about taking walk-ins. No big surprise, but they have great gelato.

Pequod’s Pizza

2207 N. Clybourn Ave., Lincoln Park | 773.327.1512

It’s kind of blasphemous to visit Chicago and not indulge in a deep-dish pizza, and the pan pies at Pequod’s (they’ve been churning them out since 1970) are the best money can buy. Sure the crust is simultaneously crispy and pillowy and the toppings bountiful, but it’s the extra layer of cheese between the dough and the pan that’s helped them stand the test of time.

Real Good Juice Co.

1647 N. Wells St., Old Town | 312.846.1897

This Old Town juicery goes to great lengths to make their cold pressed juices (and smoothies, yogurts, salads, snacks…) live up to its name. A dedicated juice chef takes care of sourcing (all local, always organic), and the hilariously punny names make remembering your favorite blends easy (Juice Springsteen, Punky Juice-ster, Juice-tin Bieber—you get the idea). Plus, the space itself—all white save for the occasional bursts of neon—is nice for a mid-day breather.

Doughnut Vault

111 N. Canal St., West Loop

Doughnuts have been enjoying a pretty awesome resurgence, and nowhere is that more evident than this family of bakeries, where out-the-door lines are a daily occurrence. Flavors run the gamut from buttermilk to gingerbread stack, but the award winning glazed is the long-standing favorite. For diehards, it might be worth it to hop from shop, to shop, to truck as the menus and daily specials vary. The truck, for example, serves strictly old fashioneds (check twitter to find out where it’s parked). Keep in mind that all three can shut down unexpectedly if stock runs out. (The other standing location is in River North.)

Heritage Bicycles

1325 W. Wilson Ave., Uptown | 872.806.0639

We teamed up with Heritage as part of our Chicago pop. After all, this is the kind of family-run operation that can make all your bike-related dreams come true. Not only will they custom build one pretty much from scratch (Tassels? Glitter? No problem!), but they make great coffee, too. The original Lincoln Avenue outpost (owners Mike and Melissa Salvatore actually live upstairs) does both in addition to a sweet general store, while the newer Heritage Outpost in Uptown is devoted entirely to coffee. You'll find free Wifi, and a group of people working on laptops, at both locations.

Blue Door Farm Stand

843 W. Armitage Ave., Lincoln Park | 773.935.2583

Part neighborhood café, part grocery, this Lincoln Park favorite is the definition of farm-to-table: All seasonal ingredients for the café and fresh produce for the market either come from the Blue Door farm, which is situated on what used to be Oprah’s property, or a number of other local purveyors. The eat-in menu has six grilled cheese varieties and a selection of craft beers while the small dry-goods section offers house-made pantry stockers and giftables from Chicago Candle Co., and goop-approved Murchison-Hume.

Owen + Alchemy

2355 N. Milwaukee Ave., Logan Square | 773.227.3444

When it comes to juice bars, many are of the seen one, seen them all mindset. But there’s nothing sunny or too crunchy about this Logan Square “juice apothecary”—the earthy, minimalist interior, lab coat-clad employees, and mood lighting give it kind of a goth vibe. Even the packaging—sleek, vintage-looking glass bottles—is too beautiful to chuck, which is why owners Jared Van Camp and Anne M. Owen (superstar chef and publishing industry vet, respectively) encourage customers to reuse bottles as vases or water vessels; there’s also a comprehensive recycling program in place.

Dollop Coffee Co.

860 N. Dewitt Place, Gold Coast | 312.600.6346

While Dollop has expanded across Chicago over the past 10 years, it’s still very much the neighborhood coffee house at heart—there’s nothing slick or overwhelmingly modern about any of the cafes. At the original Uptown spot, the seating options include lived-in couches and upholstered chairs, which if you’re in it for the long haul, makes a difference. The food offering, while modest, will do the trick in a pinch. The Streeterville location is spacious and well suited for study groups or casual meeting. Want fresh-baked pie to go with your coffee? Evanston serves Hoosier Mama pie all day. Perfectly brewed Metropolis coffee is consistent throughout so check out the Lakeview, and Downtown, too.


1233 N. Wells, Old Town | 312.548.3319

Chicago-based Intelligentsia ushered in a new wave of gourmet coffee shops, the kind where responsibly sourced and expertly roasted coffee is prepared using methods that, though time-consuming, result in a pretty perfect cup. As a rule, all outposts are aesthetically unique (five others are scattered in the Loop, Lakeview, Millennium Park, Logan Square, and Wicker Park), offer free Wifi, and loads of seating options. Plus, you kind of have to love the theme-dressed baristas.

RH Chicago, The Gallery at the Three Arts Club

1300 N. Dearborn St., Gold Coast | 312.475.9116

It's no secret that we're RH fans at goop HQ, but RH Chicago is really its own self-contained wonderland—you'll find a top-notch lunch spot, where you can choose to eat in the Grand Courtyard (a light-filled, extremely comfortable space that really lives up to its name), plus a more casual café with espresso and fresh-baked treats, and a glamorous wine vault and tasting room. Of course, there's also the stunning 70,000-square-foot display of RH furniture, which is art in itself. The best part: The gorgeous courtyard is shielded from the elements with a lofty glass and steel roof, which means you can revel in it even in the dead of winter—an experience that really can't be overstated.