Easy, If Breezy, Chicago: A Brief Guide For New Yorkers

Say the words "Windy City" and by free association, we all think: Oprah, Obama, deep-dish pizza, Da’ Bears, and "brrrrr."  But there’s so much more!Dazzling architecture, outstanding city views, cordial Chicagoans, quirky neighborhoods and sunny, 60-degree mid-November weather––those are just some of the highlights of my recent 48-hour family trip into town. By "family," I mean me, a thirtysomething free spirit, and my parents (just imagine the crazy side of The Fockers). Could Chi-town handle us?

Upon arrival into O’Hare, we jumped on the easy-to-navigate, not to mention uber-clean CTA (Chicago Transit Authority) and transformed quickly from savvy New Yorkers to dopey tourists, as we tried to understand the no-change metro machine policy. Luckily a CTA employee was helpful and midwesternly, and got us through the turnstyle gracefully.

We landed at our hotel, the JW Marriott––the baller of all Marriott’s––in the bustling, business-oriented Financial District. Located in a renovated historic national bank building, the shiny, marble hotel lobby and lounge was a nice, warm welcome.At nearly 500 square feet, our airy room offered everything we needed: two beds draped with fluffy duvets, a spa bathroom clad in Italian marble with a stand-alone tub, and supersized terry cloth robes.

Service was top-notch. For example, after some slight confusion over our room temperature (I’ll take full credit for that one), the front desk immediately had an engineer at our door. We called down a few other times for more bathroom products and additional pillows; everything was "no problem." The concierge helped us with maps and routes constantly––we wouldn’t have made it far without him.

At night, we’d sit with our laptops or novels in front of a cozy gas fireplace in a quiet corner of the lobby. How charming for a hotel we assumed was strictly a corporate hang. Good people watching too––wedding parties, football fans, first dates. Refreshing (and free!) orange cleansing water in the lobby kept us hydrated and happy.

But let’s discuss beyond the hotel. 

The first place we went was Magnificent Mile; about a 15-minute walk away, which initially, alarmingly, sort of felt like Times Square. Streets were crowded, tourists were crammed together. I worried we’d entered a bit of a migraine. That is, until we stumbled upon the iconic Wrigley Building. Powerful, stop-in-your-tracks, absolutely stunning!

Lunch was at the famous Giordano’s Pizza. While we wanted to try Chicago’s famous deep-dish pizza, they only offered deep-dish crusts stuffed to the nines. This concept, us pizza purists found unappetizing, so we chose a basic thin crust pie. It was decent, but we’ve had better, like Grimaldi’s in Dumbo. Just a small strike, Chicago. (By the way, what’s a New Yorker doing in Chicago if not to say our pizza is better?!)

We were then off to Wicker Park, an edgy neighborhood dotted with vintage stores, cute coffee houses and loads of shopping options. The locals were a mix of real-deal artists, grungy hipsters and Lululemonized stroller moms. One trendy term that could be applied? Très Brooklyn. We felt right at home.

We hopped the subway after a few hours, and then took a bus to Hyde Park to see the Obama’s house. This was really exciting, especially to be there right after the election! We tried to bribe the secret service at the edge of his street for more personal scoop, but no luck. Alas, we were perfectly content just checking out the nice-but-modest digs.

Meanwhile, Chicago and the Chicagoans were really growing on us! Locals kept helping with directions and advice, and everyone was just so nice and patient. Every so often, we’d catch a glimmer of glamour on the regal streets. My mother alluded to Champs-Elysées more than once.  

We stopped at the Willis Tower SkyDeck—in the former Sears building—and rode up to the 103rd floor. I pushed my fear of heights aside as much as I could, and I’m glad I did. The view was breath-taking as we could see about 40 miles of city landscape, plus Michigan, Indiana, and Wisconsin. Don’t think my dad didn’t try to also re-enact the scene from Ferris Bueller’s Day Off that was filmed here.

For dinner, we shared plates at the celebrated Sable Kitchen & Bar, a gastro-lounge in the center of the River North neighborhood adjacent to Kimpton’s Hotel Palomar. Spearheaded by Top Chef alum Heather Terhune, her seasonal dishes were out of this world. The menu was well balanced, as there was something for all of us, which, with a vegetarian mother and a meat-n-potatoes father, doesn’t happen often.

We started with the Butter Lettuce & Apple Salad with radicchio, grapes, smoked cashews & almonds and sherry-apple cider vinaigrette. Easily, the best salad of our lives. Our other favorite dishes were the brick oven flatbread with rosemary, brie, and house-made ricotta, butternut-squash apple soup, mini wild mushroom veggie burgers with red onion jam, and short rib sliders. This would definitely, no question, be our new family go-to spot if it were in New York. The food was fresh, flavorful and mouth-watering. Service was exceptional as the food came out perfectly timed to give our stomachs a brief rest. The dining room felt both calming and luminous. The staff was professional, warm and had serious culinary swagger. If you go to Chicago, you’d be crazy not to run here!  

We also had a lovely breakfast at Hoyt’s Chicago, inside Hotel 71, near Millennium Park. A sweet spot, with a nice street view. I very much appreciated that Hoyt’s is also part of my illy coffee cult.

At the end of our stay, we didn’t want to leave. Chicago embraced us New Yorkers in a way we never expected. I’m happy to say, it’s a city I’m now totally in-sync with and can’t wait to touch down here again.

4 Out of 5: Leslie Garry & Amy Goetz on Chicago

Leslie Garry and Amy Goetz are cofounders of Delve Chicago. This is their take on four places they like, and one place they don’t.

RECOMMENDED

Davanti Enoteca – "A top-notch, smal-plate restaurant in the heart of Little Italy complete with a wine retail shop and cozy rooftop dining? Yes, please. Executive chef Jonathan Beatty offers up dishes that are meant to be shared, though parting with your risotto carbonara is easier said than done. Healthy eaters beware: Davanti loves truffle oil. And egg. A lot. Leading to our favorite dish on the menu, the truffle egg toast with fontina and asparagus."

Dose Market – "Once a month, the best that Chicago has to offer congregates at this uber-stylish fashion and food market in Chicago’s River East Arts Center. Local vendors feature food that ranges from artisanal breads to bourbon-barrel-aged syrup and fashion/crafts ranging from hand-made jewelry to exclusive-to-the-market styles for both men and women. Sipping rare tea and eating champagne gelato while shopping for luxury vintage? Trust us, there’s no better way to spend a Sunday."

Sarca – "This eclectic boutique is nestled in the Gold Coast among other fashion greats like Ikram and Sofia Vintage. A spot for one-of-a-kind pieces that you can find nowhere else in Chicago (or the US for that matter), Sarca is the go-to spot for Chicago women looking for highly curated picks. Think European designers like Alice by Temperly, Issa and Markus Lupfer, complemented with local jewelry designs by up and comers like Damen + Division. A destination in its own right, stop by Sarca to feel a little bit of worldliness, right in the Midwest."

Telegraph Wine Bar – "A favorite spot for dim-lit dining and French rosé-sipping in the middle of Chicago’s ‘it’ neighborhood of the moment. Wine director Jeremy Quinn focused his wine concept on natural wines of Europe to accompany the restaurants locally sourced, pan-European eats. All of the experts at Telegraph were handpicked as the best of the best from an impressive lineup of other Chicago hotspots, including Bluebird and Avec."

NOT SO MUCH

Giordano’s, Original Gino’s East, et al – "Most Chicagoans take their pizza very seriously, and we consider ourselves V.I.P (very into pizza). We’ve never been traditional gals, so we tend to go thin crust, not Chicago style (can I even type that while in the city limits?). Yearly deep dish noshing is reserved for appeasing pleading out-of-towners."

Where Celebs Go Out: Steve Carell, Tina Fey, Ben Stiller, Alan Cumming

At the Date Night premiere: 1. Steve Carell – “Boy! You know what? On the way in, we drove by Shun Lee. My wife and I, when we lived here, we ate there all the time. John’s Pizza was one of our favorite pizza places. Any one, but, certainly, the one in the Village, and I think they opened one up off Times Square. That’s just always good.” 2. Tina Fey – “My favorite restaurant in the world is a restaurant in Chicago, called the Athenaeum Room. Favorite dish? Chicken on french fries.” 3. Taraji P. Henson – “The Little Owl. I went there the other night!” 4. Jimmi Simpson – “Providence, on Melrose, in Los Angeles. Any special dish? The five-course tasting menu.” 5. Carol Alt – “Actually, I like Pure Food and Wine because it’s a raw restaurant. What do you like there? Well, just about everything, but their ice cream is killer! Raw ice cream — unbelievable, unbelievable. I eat at a lot of Japanese places, so I can have raw fish. I’m a raw foodist, so it, kind of, limits.”

6. Common – “I love Café Habana. It’s located on Prince and Elizabeth. I’ve been, consistently, going there. It’s not anything new. I’ve been going there for, like, 10, 11 years. Cuban food; great music. You got to eat the corn. The corn is the best. I like the camarones, too — the shrimp; they’re incredible. I also enjoy a place called Stan’s, in Brooklyn. It’s like Cajun, but new food. It’s like New Orleans, but slash some other feel to it. It’s a great restaurant. I’m a restaurant guy more than a club guy. I like going to the movies different places, like, what’s the one on Houston? The Angelica. I love that.” 7. Serena Williams – “I don’t go to restaurants here, so–.” 8. Jane Krakowski – “Can’t think of any. Sorry!” 9. Shawn Levy – “Well, I’ll go with New York. I like– I ate there last night– Scalinatella, at like 61st and Third, that place underground. I like Nobu. That’s really not surprising. I like Cafe des Artistes, with that great antipasto cafe. Does that give you enough? All right.” 10. Ben Stiller – “Bar Pitti.” 11: Keith Powell – “I live in Brooklyn, and I live in Fort Greene. And in Fort Greene, there’s a restaurant called No. 7. And No. 7 is the most amazing restaurant. The head chef is a guy named Tyler Kord. And he used to be the sous chef for Jean-Georges. And the menu changes every month, and he comes up with the most amazing concoctions, both in terms of drinks and food. It’s wonderful. Anything that man makes is, kind-of, a work of art.”

At the YourSingapore launch in Times Square: 12. Matt Harding – “Oh, my gosh, I’m totally blanking on– I love garlic, so I love The Stinking Rose restaurant in L.A. and San Francisco. They just drench everything in garlic. You’re sick the next day, but it’s fantastic! My favorite restaurant in Seattle– I love Tom Douglas. He’s a Seattle chef. He’s at the Dahlia Lounge. New York, there’s just so many fantastic restaurants, I couldn’t think of one. And Singapore, actually, my favorite place to eat is out on the street. The Hawker markets are fantastic! Where’s your next stop? I’m going home to Seattle, and then maybe to Afghanistan.”

At the NY International Auto Show benefit preview for the East Side House Settlement: 13. Fe Fendi – “I like Le Cirque. It’s like going to a family restaurant for me. For lunch, always Cipriani! Cipriani for lunch — dinner at Le Cirque.

At Dressed to Kilt: 14. Alan Cumming – “Gnocco in the East Village.” 15. Shani Davis – “I live in Chicago. My favorite restaurant — fast food — is Harold’s or, maybe, Portillo’s. I love Giordano’s a lot.” 16. Eric Daman – “I’m a huge fan of the Mercer Kitchen. I love their mac and cheese and their carpaccio sea bass.” 17. Kelly Killoren Bensimon – “My ultimate favorite restaurant is Le Bernardin–Eric Ripert– he catered my wedding. It’s, probably, the most incredible restaurant, actually, in the world. But one of my favorite restaurants is Brinkley’s, which is right around the corner from me. It’s a really, really, cool, fun bar, and one of my friends that went to Trinity — ’cause I went to Trinity — went there, so I go there a lot. Any favorite dish anywhere? Wherever– whatever– I like to explore and have fun with the menu. I really, really like and what they’re making is more exciting than just for me to sit there and be like, ‘Yeah, I’ll have rice and vegetables. This is really fun.’ I’d rather have someone make something and be creative.” 18. Al Roker – “Oh, golly! That’s like asking, ‘What’s your favorite kid?’! If it’s Italian, it would be Girasole or Fresco. If it’s a steak place, it would, probably, be Ben Benson’s or across the river, Peter Luger’s.” 19. Nigel Barker – “Del Posto. I love that place. I used to go there on dates all the time. My favorite pub is Dublin 6 in the West Village. It’s my old, local Irish place — D6. And Barbuto is another favorite of mine. It’s not as upscale. It’s, kind of, in between the two. It’s on Washington.” 20. Donald Trump Jr. – “Wow, that’s a — in New York, there’s really no shortage of great restaurants, but, I guess it depends what food we’re going for. If we’re going formal, Jean-Georges is good; Le Cirque is good. If we’re going low-key, there’s a lot of great ones lying around. We’re opening up a great one on Friday — Quattro — in our hotel down in SoHo that’s going to be opening, so a little bit of a Miami, downtown flair.”

Promoting Burlesque to Broadway: 21. Quinn Lemley – One of my favorites is Maloney & Porcelli. They have a great wine dinner that’s all inclusive, and wonderful steaks and oysters. There’s a new Academia del Vino that’s up on Broadway and 89th. It’s where Docks used to be. They have a great wine bar and wonderful food. It’s the same people that have Cesca— it’s that restaurant group. And it’s very happening. It’s so exciting to see something on the Upper West Side above 86th Street.

At Our Family Wedding: 22. Mark Indelicato – “I like to go to places that aren’t mainstream chain restaurants. Sometimes, I’m just walking down the street with friends, and we see like this small, little cafe, and we just go in. Don’t even know the name of it, don’t know what it’s about, but I just like the small, boutique restaurants, like Alice’s Teacup here on the Upper West Side. It’s small and not a lot of people know about it, but it’s still really cool.”