Chicago has been on my list of American urban centers for some time now. I have spent many a layover sprinting through the O'Hare airport trying to catch a connection, but had never actually set foot in the Windy City. Perhaps we didn't quite think through the truth in that moniker when booking flights to Chicago in the middle of JANUARY, but despite the wind chill and store-to-store sightseeing we resorted to, the clear skies and warm vibe of the city kept my friends and I entertained and toasty during our 3-day jaunt.
Southwest flights from LaGuardia to Midway airport (Chicago's lower-key cousin) fly often and inexpensive, if purchased in advance. My friend Emily has extended family and strong ties to the Chicago area, so she served as the tour guide to myself and fellow newbie Joanna. We were all extremely close friends in college, but Joanna lives in Philadelphia now and it's harder for all three of us to stay in touch consistently with all the demands of our jobs and such, so it was a rare and wonderful treat to book a whole weekend girls getaway. We were able to spend most of Saturday relaxing at Emily's grandmother's house after our very early flight in, and then saved a few Uber bucks with a ride into the heart of the Magnificent Mile where we checked into our aptly-named hotel just off Michigan Avenue, MileNorth Chicago.
MileNorth is just a few minutes walk from the gram-worthy Millennium Park and famous bean sculpture (technically called CloudGate), and since Saturday promised to bring the warmest temps of the weekend (a "feels like" of 18 was positively sweltering), we thought that would be the most logical place to start the weekend. After taking the requisite selfies in the bean's silvery reflective surface and checking out the line for skate rental at the Ribbon (too long), we wandered around the grounds of Millennium Park and down to Chicago's fabled waterfront area. The piercing blue of Lake Michigan almost made us feel like we were in a Caribbean isle, but the boulder-like ice floes bobbing around the empty piers suggested otherwise. The lake and river-front bike path was perfect for a brief stroll back to the hotel, where we thawed out and 'grammed some of our best finds.
Many of Chicago's attractions, notably the beachy lakefront and carnival-esque Navy Pier might be better experienced in spring or summer months, but there's one regional draw that doesn't depend on the mercury, and that's food. When connecting with colleagues and friends who had gone to school or lived in Chicago, I heard a lot of good things about the various neighborhoods north of downtown, like Lincoln Park, Logan Square, and Wicker Park, so we tried to experience neighborhood flavor by splitting an Uber to Cafe Ba-Ba-Reeba!, a top-rated Tapas restaurant in Lincoln Park. The spot was clearly popular, judging from the crowded bar, multiple birthday celebrations, and the only-available 10 pm reservation. For good reason, too: we waited out our early arrival with a pitcher of the house white sangria, floating with orange and apple slices and just sweet enough to get me thinking hard about my plans for the menu. Once seated in a back patio (enclosed, luckily), we wasted no time pointing at decadently-described small plates on the menu and ordering up a slew of hanger steaks, brussel sprout salads, fried chicken thighs, and mushroom toasts. The amount of food was significant but not overly indulgent, although the three free desserts (be sure to check in on Yelp!) may have pushed us over that edge. The real kicker here was the jaw-droppingly affordable bill: split three ways, we each paid just 22$ for a multi-course sophisticated meal at one of the city's trendiest spots. You don't see those prices on the East Coast, huh?
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| #YolkPorn courtesy of Emily Johnson |
We killed time by checking out Wormhole Coffee next door, which is an all-80s pop culture and film celebration, complete with a full-size Delorian posted on a loft in the back, old computers by the creamer stand, and action figures packed in a glass-top table. We had a warm-up caffeinated beverage before getting seated at Bongo, whose separate brunch, breakfast, and special menus were equally enticing. I settled on a turkey sausage breakfast sandwich (the pretzel roll sold me); Emily got lobster Eggs Benedict (yep) and Joanna opted for a simple egg and bacon dish with a BONUS white chocolate caramel pretzel pancake. Yep, you can order single pancakes here, truly the best of both sweet and savory worlds.
Wicker Blvd is lined with independent coffee shops, used bookstores, and mostly clothing boutiques and vintage stores. we strolled from store to store, using each new boutique as an excuse to get out of the whipping wind. We purchased very practical fleece-lined leggings (a steal at $8 and BOGO free) that served as our next-day and flight attire, and I scored at the Buffalo Exchange. Wallets burning, we decided to get back to town for a main tourist activity: riding the elevator to the Skydeck at the Sears-turned-Willis-turned-Willis-Towers-Watson Tower, once the tallest building in North America.
The stark black skyscraper is an icon of the Chicago skyline, already notable for its influential architecture and detail-laden buildings. Standing in line for the $22 elevator ticker, we learned all sorts of fascinating tidbits about the construction and day-to-day operation of the tower. But the real thrill was, of course, the plexiglass pushed out boxes that are nearly exclusively a photo-generating machine. One lady down (those heights get the best of us), we made our way around the 360-degree Skydeck view, taking in lake to the east, towers and skyline icons north and south, and a view of neighborhoods and eventually fields and suburbs to the west. It was startling clear (one perk of the cold!) and when we sat down for a picture in the stomach-dropping suspended glass boxes was memorable, the 1 degree air went straight through the jeans! Chilly and nearly touristed out, we descended and prepared for the excursion of the weekend: a Blackhawks game with our one-true-fan tour guide, Emily Johnson.
A huge shoutout to Emily and her family for providing us with great tickets for what turned out to be an amazing game. Emily knows all the history, showing us the statues of hall of fame players in front of the United Center and talking us through the historical montages on the Jumbotron. Luckily the game didn't lack in action, with the Blackhawks solidly crushing the Canadiens in a back-and-forth 5-2. Several beers and goal sirens later, we hit up another Chicago (and apparently midwest) tradition: Howl at the Moon piano bar. Here, aspiring musicians duel at facing grand pianos, taking song requests in order of highest tips. The players rotate between pianos and playing backup bass and drums, as well as singing everything from Billy Joel classics to Rihanna and Bieber. Thanks to two rum bucket cocktails, we stomped and sang along for the better portion of the night, never tiring of the mix of music styles and live performance. [Sorry for my drunk singalong voice in the video.]
Awake and hungry again, of course, we hustled to a hungover breakfast just one block from the hotel, Sunny Side Up. I guess their menu descriptions served them well because all three of us ordered goat cheese and balsamic eggs Benedict, a delicious and all-curing combination. The coldest day of all and our last in the city, we visited the 7-story Water Tower Place mall and forced down some deep dish pizza (sorry, Chicago. You struck out on both pizza attempts. $1 thing crust slice any day.)Full of traditional treats and midwestern charm, we took off for the airport around mid-afternoon, closing out a well-rounded weekend in a new and favored city. Thanks to the tour guide leadership of Emily and a handful of well-taken recommendations, I have to say this chilly city has my vote for food, hospitality, and sports spirit. I'll certainly be back - in a different season, of course.
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