PHOTO: J. Parker Lounge, Chicago. (photo by Rosalind Cummings-Yeates)
Chicago is a multi-faceted big city and, as a native, I love to experience all the so-called touristy things that visitors love. From hanging out at Millennium Park to filling up on deep dish pizza, I appreciate all of my city’s offerings.
So, when I was invited to check out Chicago using the Trip.com app, I jumped at the chance to organize a staycation itinerary.
Trip.com is a travel planning website and app that uses artificial intelligence to predict what you’d be interested in for your travels. It’s the first travel app to be context aware; using predictive technology about contact and preferences, it helps travelers discover where to go next.
So, I dived into setting up my profile, which focuses on choosing from the 19 tribes that categorize your interests. It was hard to narrow down the choices which include nightlife lovers, spiritual seekers, adventure and budget travelers, but I selected local culture, foodies, trendsetters and art & design lovers to define my travel style.
From there, personal recommendations for hotels, restaurants and activities popped up on my profile, which I honed into my “Chicago List”, which is basically my itinerary for a weekend centered around the Lincoln Park neighborhood.
I really liked that you can book hotel and restaurant reservations directly from the website so all of my travel plans were neatly outlined in one place. User reviews are also a good way to figure out what fits and what doesn’t. With the app laying out my itinerary on my phone, I took off for a winter staycation in Chicago.
The stylish Hotel Lincoln was my choice for a hotel because I wanted to stay in Lincoln Park, close to the activities that I wanted to do. A boutique hotel with charming rooms and the trendy J. Parker rooftop lounge, I loved Hotel Lincoln’s eclectic decor and welcoming service.
After an afternoon check-in, I dropped my bag off in my room overlooking Lincoln Park and headed out for a matinee at the historic Music Box Theatre. I love this 20s era theater because it shows independent, cult and foreign movies that you rarely find anywhere else, plus it boasts a cute lounge where you can sip cocktails, coffee or tea. I took in a 1930s, pre-code movie called “Freaks,” which tells the riveting tale of circus sideshow performers (including Siamese twins, little people, and performers without arms or legs) who exact revenge on a trapeze artist who abused one of their own.
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For lunch, I sliced into the caramelized crust of Pequod’s Pizza, a local fave that is always bursting with people. As a Chicago deep dish aficionado, I frankly wasn’t impressed with the pizza compared to other local standbys but it hit the spot on a cold winter afternoon. I strolled across the street from my hotel to take in the balmy environs of the Lincoln Park Conservatory. I enjoyed the annual “Winter & Train Show,” which is a festive presentation of lanterns, lighted evergreens, model trains and winter blooms.
I returned to hotel Lincoln to relax and check out the twinkling views at J. Parker Lounge. The bar features cozy tables, benches and couches under strings of glittering lights. It also boasts small plates and dazzling views of North Avenue Beach and Lincoln Park.
I hopped into an Uber to arrive at the hot West Loop dining destination and one of Chicago’s most popular restaurants Girl & The Goat. Top chef Stephanie Izzard’s pride and joy shows no sign of slowing down, as it was crammed with people, as usual. Impeccable service helps overlook the noise and crowds and the sophisticated dishes, including bleu cheese sweet potato pierogies, escargot ravioli and braised pork shank with kimchee are standouts.
I topped off my night with a visit to Uptown Underground, a local cabaret that features magic shows, vaudeville -influenced acts and the Kiss Kiss burlesque troupe. I caught the late night burlesque performance and reveled in the creativity that included hula hoops, furs and, of course, sparkly g-strings. I rolled into my bed at Hotel Lincoln for what seems like a few hours before it was time for me to grab brunch at the super popular Batter & Berries.
This small Lincoln Park spot is always overflowing with diners and I wanted to find out what the fuss was about. Reservations aren’t accepted and hour-long waits are common but I lucked out with only a 15-minute wait. I sat at a long communal table and dipped into the best breakfast I’ve tasted in Chicago. I ate the Jamaican Jerk egg white omelette, filled with smoked salmon, shiitake mushrooms, white cheddar, sauteed spinach and jerk sauce, with a side of caramel french toast.
Needless to say, it was foodie perfection and I checked out of Hotel Lincoln, ending my Chicago staycation stuffed and happy. Thanks to Trip.com, I had re-discovered parts of Chicago that had fallen off my radar but now they’re back for a long stay.