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.