Confession: I thought I knew enough about Chicago. Thanks to a college roommate hailing from the suburbs of Chi-town and two quick visits to see her (plus everything I’ve seen thanks to the team behind The Everygirl (thanks ladies!), I thought I had seen enough to get it.
I was wrong.
It was an incredibly fun long-weekend trip. Flying in Friday morning and leaving Monday night, we had plenty of time to check off the most touristy parts of the city (looking at you Sky Deck and deep dish pizza), while doing what we do best on trips – brunch and walk, walk, walk. If you’re planning an upcoming trip to the city, here’s a look at what we did to get you started.
DAY 1:
This is a side note, but did you know that when the famous run-through-the-airport scene was shot for the first Home Alone movie, there was no area roped off to film. When the McAllister family sprints through O’Hare, that really was a normal day in the airport, with actual travelers in the background. The production staff had to chase after people to have them sign waivers, but how crazy, right? Anyways, taking the train from O’Hare Airport into the city is really easy and in 40 minutes or so, you’re in downtown Chicago!
As much as I oggle beautiful hotels on Instagram, I don’t need to stay as particular brand when I travel. What I care most about is affordability, location and general safety/cleanliness because most of the time, I’m there to be out in the city and will only be sleeping in the room. Luckily, my travel partner agrees and found a dime spot downtown in the theater district. The Cambria Suites which was a perfect location — close to the train and some of the city’s best known treasures (Millennium Park, Grant Park, The Art Institute, theater district), it ended up being a fantastic place to stay. There was even a Garrett’s Popcorn next store (there was a line waiting for it to open in the mornings!) and, maybe my favorite, the Joffrey Ballet was just half a block down from us. You could look up as you passed by and see dancers working at the barre. It was major Center Stage vibes.
Because we were so close to the Bean (did you know that’s not actually the work of art’s name?), we made it our first stop and christened the visit with a Chicago hot dog. I mean, if you go to Chicago and don’t visit the Bean, did the trip really happen?
After the hot dogs, we made our way through downtown to something I’ve wanted to do ever since I first saw My Best Friend’s Wedding … a riverboat cruise. There was no Julia or Dylan in sight, but the tour was such a fantastic introduction to the city. Our guide was amazing and shared so many tidbits about the city … like, did you know that the name Chicago stems from a Native American word “shikaakwa” that means “land of wild, smelly onions”? Or that Frank L. Baum lived in Chicago at the time of the city’s first World’s Fair and it’s said that the the number of white buildings erected for the exposition inspired the creation of his Emerald City? More than anything our tour guide told us about the exceptional architecture that fills Chicago. Such an incredible feat of creativity and ingenuity — even for me, someone who knows very little about buildings, it was super fun to learn about.
After the boat tour, we grabbed an early dinner at a recommended deep dish spot, Labriola. You’ve never had deep dish, it is rich to say the least. One and a half slices and I was done — but Labriola does it well. We were able to snag seats outside which made the meal even lovelier with people passing by and a cool spring night beginning around us. I had forgotten that it takes on average 45 minutes for a deep dish pizza to cook, but we got lucky with a light crowd in the restaurant. We had our pizza in just over 20 minutes, which means we had time to go back to the hotel and change. Three cheers for not having to go to Hamilton in my sweatpants!
Yes, that’s right … we were on a schedule because we had tickets to Hamilton our first night in the city. I posted about it on Instagram, but I went in to the show very hesitant about whether or not I’d like it. How in the world could it live up to the crazy-high bar everyone in the world seems to think it lives at? Well, it surprised me, it fascinated me, it moved me. The cast was incredible, singing their guts out all way to the rafters which is basically where we were (very last row of the tip top balcony). And I walked back to the hotel after the show with my hand over my heart, not quite ready to let the moment, the show, all that I had seen and heard leave me yet. They’ve earned every inch of hype holding the Hamilton name up — go see it! (If nothing else, you will be amazed and reminded about the incredible beginning of the United States.)
Ah! Hamilton-level excited!
See? Tip top balcony!
(Hamilton ceiling!) Ha — all the ! for Hamilton.
DAY 2:
We started Day 2 off with a DE-LIGHT-FUL discovery in the from of Stan’s Donuts. Spotted en route to brunch (yes, we stopped for food on the way to food), Stan’s was a donut wonderland. Blueberry fritters bigger than our hands, cake donuts, sprinkle donuts, cronuts! (Sadly, I discovered I am not a fan of the cro-nut … the filling is was ruins it for me.) Stan is the man which is why we made this our first — but not our last — visit of the trip.
After Stan’s and brunch — we were committed to food on this trip! — we ambled around downtown for a while and decided to take a detour to Armitage Ave., a boutique-y street full of shops to bop in and out of. As we shed our layers with the afternoon sun, we made a stop at Jeni’s Ice Cream before tottering further into the afternoon.
We happened to notice as we were mapping our walk from Armitage to Second City for a comedy show that we were close to Oz Park. Intrigued, we made a detour. The park celebrates the famed book that was written by Chicago resident Frank L. Baum with statues of the four most-beloved characters, Dorothy, the Scarecrow, the Cowardly Lion and the Tin Man. Short on time, we could only spot two of the four, but it would be fun to go back and find them all.
After our Second City show, we decided it was high-time for a drink and Restoration Hardware was just the ticket. The restaurant and bar inside the store are just as jaw dropping as photos suggest. It’s a dreamy world of garden meet gala with chandeliers, luscious couches and prosescco a plenty.
What I most love when visiting cities is walking — that’s how you really start to get the feel of a place as you weave between locals on the sidewalk. As we left RH and started our walk back to the downtown area, I caught all kinds of details and glimpses into what must be everyday Chicago life — dry cleaner shops on every block, couples having a glass of wine on their front stoop, people out for walks with dogs or babies at twilight and a widespread support of ivy everywhere.
DAY 3:
We started Sunday with brunch down the street at Le Pain Quotidien and then kept going down the street for a visit with the Art Institute. Because we had purchased City Passes (we used ours for the architecture boat tour, the Art Institute and the Sky Deck) we got to bypass a crazy long line and walk right into the museum, have our passes scanned and keep going. It’s a money and time saver.
Anyways, the Art Institute! I’ve always wanted to go there because it’s home to my favorite painting, “Paris Street, Rainy Day” and a large collection of impressionism art. Ever since I first learned about the art moment in 10th Grade French class, I’ve loved it. Those artists broke out of the traditional norm of their day, choosing to celebrating the beauty of small, everyday things. They slowed down and took great notice of the tiny moments of daily life — light reflecting off the water, people sitting at cafes, wild flowers on a table — all slices and moments delivered in worlds of color that let you wander off and lose yourself in their many, many layers and brush strokes.
It ended up being a spectacular day so after the museum we stopped for iced coffee and then wandered through Grant Park and Millennium Park. Several weddings were being set of for later that day, we spotted sail boats making their summer debuts just beyond shore and the parks were milling with light crowds. It was a great way to spend the afternoon before meeting up with friends who coincidentally were also in town. If your’e ever looking for a rooftop spot to nosh and sip something cool, Cindy’s delivers an incredible view of the park below.
Our last stop of the night was dinner at Quartino. I first heard about the restaurant from my favorite writer, Shauna Niequist, who is a Chicago native. I had read her hearty, raving reviews and knew we had to experience the small plate spot. I also posted about it on Instagram, but it was utterly charming and exceeded what I expected. So glad we got to spend a few hours under their hospitable care.
DAY 4:
Last day! We needed another fill of Stan’s Donuts before we left town so, of course, we made it our first official stop of the morning. We downed our blueberry fritters on the stop but both took another donuts to go (chocolate sprinkle cake for me). Dosed with carbs, we made our way to the Willis Tower and Sky Deck experience. Truthfully, we had tried two other times on the trip to go up in the tower. Lines can be hours long for the attraction — which is why we turned around the first time times we visited — so we crossed our fingers as we entered the lobby and down the escalators that we’d be able to make the 103-floor ascent. Luckily, the wait was just about an hour and lines moved fast. (I think it helped that we were there early in the morning.) Once up in the tower, we waited our turn for the sky deck. You’re allowed 60 seconds out on the glass and even for me, someone who isn’t ever afraid of heights, hesitation before stepping out onto the glass was real.
I’m not usually one for the major tourist spots like the Willis Tour, but after stepping out of the box, I was glad we had made the trek. I mean, how often can you find yourself in one of the country or world’s tallest tours?
The visit was quick enough that we had time to swing through the Lincoln Park Zoo, but because of an incoming storm, didn’t stay long. We dashed back to the hotel, grabbed our bags and headed to O’Hare. A quick, but memorable trip full, it was full of delicious food, great views, some experiences I’ll never forget (Hamilton!) and a better understanding of another corner of the country and world.
