4 Days in Chicago: A Journey through Art, History, and Gastronomy
Looking down the Chicago River
The last time I set foot in Chicago was nearly a decade ago. I was there for a graduate school interview, and save for the inside of several classrooms and lecture halls, I did not see much of the Windy City. I flew in one morning and flew out the next (to make my way to yet another interview). Ever since then, I have longed to return and do the city justice, and last year, I had the chance to do just that. My husband and I traveled there for a long weekend in March, and here is what we got up to while we were there.
Day 1, Friday: Early Morning Flight and Art
At the ungodly hour of 4:00am, our alarms went off, and my husband and I dragged ourselves out of bed. We awoke to less-than-stellar news: after what had thus far been a mild winter, Chicago was forecast to get up to eight inches of snow accompanied by winds hovering around 45mph. Concerned that we would arrive in Chicago only to become snowbound in our hotel, we briefly considered canceling our trip, but upon seeing that the snow would let up by evening and that the following day was supposed to be sunny and in the 40s, we decided to press on.
So, without further delay, we finished getting ready and hailed an Uber to take us to the airport. As luck would have it, we got a driver who wanted to avoid tolls, so rather than take the more direct route of the Pike (I-90 to you non-Bostonians), he took the scenic way and caused us to almost miss our flight. We arrived at our gate as they were nearing the end of boarding, much to the dismay of my grumbling stomach, which would now have to make do without breakfast.
Looking down at Boston
The flight was largely unremarkable. We departed 15 minutes behind schedule at 6:30am, and two hours and 45 minutes later, we touched down in Chicago. In typical fashion, I failed to get any sleep on the plane and spent the time watching shows on my iPad.
Half-asleep and borderline delirious (I was running on maybe two hours of sleep), I rolled my suitcase off the plane and down the jetway, where I joined my husband in aimlessly wandering about in search of the rideshare pick-up spot. Mercifully, we eventually crossed paths with an airport employee, who pointed us in the right direction. However, even with the correct directions, reaching the pick-up point took a little while, as we had to first wait for a train to take us to one of the other terminals. When at last we reached the pick-up location, we thankfully did not have to wait too long for our Uber driver, and 25 minutes later, we were stepping out of the car and heading into our hotel, the Kinzie Hotel.
Our room at the Kinzie Hotel
Despite arriving several hours early, we were able to check in immediately and go up to our room, which aesthetically, was quite nice. As we would soon learn though, the room had a few quirks, including a sluggish heater and water that was either scalding or frigid. Nonetheless, it was a decent room considering what we paid, and the hotel itself was conveniently located within walking distance of numerous restaurants and attractions.
One such nearby eatery was Yolk, which we headed to after dropping off our luggage in the room. Thanks to our poky Uber driver, I had been unable to have breakfast at the airport and was running on a couple of measly granola bars. I was ravenous by the time my breakfast burrito arrived, and while objectively mediocre, it tasted amazing in the way that only food that you eat when you’re starving can.
My breakfast burrito from Yolk
Contentedly full, we ambled down the River Walk a few minutes before heading back to the hotel for a spell to rest and give our breakfast a chance to digest.
View from the River Walk
A little before 12:00pm, we set out for the Art Institute, stopping at the Bean along the way. After snapping the requisite photo, we strolled around Millennium Park and admired several of the art installations.
Me posing in front of the Bean
We arrived at the Art Institute around 12:40pm, and our first order of business was to join the virtual waiting list for the Salvador Dalí exhibition that was on display from February to June 2023. We did so by scanning a QR code, and upon doing so, we discovered that the wait was over an hour. So, while we waited for the text that would notify us when we could enter the exhibition, we explored the museum’s permanent collection, beginning with the Impressionist galleries on the second floor. From Monet to Van Gogh and Renoir, there was an impressive and beautiful assortment of Impressionist paintings. Without a doubt, this corner of the museum was my favorite.
Vincent Van Gogh’s Fishing in Spring, the Pont de Clichy
We subsequently walked through the Art of the Americas wing, where we saw one of my favorite paintings, Nighthawks. Its depiction of urban loneliness is masterful, and it is one of those rare pieces of art that I could stare endlessly at. The other highlight of the American galleries was American Gothic – you know, that painting of an older, austere couple where the man is holding a pitchfork.
Edward Hopper’s Nighthawk
Around 1:40pm, we temporarily left the museum to find something to eat. We saw that there was a nearby location of Just Salad, a chain of fast-casual restaurants serving among other things salads (obviously) and grain bowls, and given that we had eaten there during a recent trip to New York and thus knew what to expect, we headed there. I ordered the Spicy Tofu Crunch Bowl, and although it didn’t live up to its spicy name, it was still quite tasty and flavorful.
Partway through lunch, we received the much-awaited-for text informing us that we could enter the Dalí exhibit (perfect timing, right? 😆). Unsure how long or if they would hold our spot in line, we quickly finished our lunch and returned to the museum.
Helpful tidbit — Your ticket to the Art Institute of Chicago is good for the entire day, so you can enter and leave multiple times on the same day.
We were able to enter the exhibit without any issues and were met with an unwelcome sight: wall-to-wall people. Despite the staggered entry, the gallery was packed, which detracted from the experience. I was unable to get a close look at several of the paintings, and even those that I could draw near, I couldn’t fully appreciate. Due to the extreme crowdedness, I felt obliged to move along and not linger. Needless to say, we did not stay long in the exhibit.
Salvador Dalí’s The Image Disappears
Personal bubble restored, we spent the next hour or so exploring other parts of the museum, including the American, Greek, Roman, and modern art wings. I particularly enjoyed the American art galleries’ collection of furniture, which featured pieces by Tiffany Studio, as well as a number of Shaker and Colonial pieces. The contemporary art galleries, while not my favorite, were at least entertaining.
The requisite blank canvas. Is it even a modern art gallery without one of these?
A little after 4:30pm, we moseyed on out of the museum and walked back to our hotel. We relaxed for a couple of hours in our room, watching reruns of Diners, Drive-ins, and Dives, and around 7:00pm, we strolled next door to Parlor Pizza to pick up our dinner of pizza (duh) and salad (so we could feign being healthy). More specifically, we ordered the All-Caps Pizza (mushroom medley, black truffle cream, smoked mozzarella, white cheddar, leeks, garlic, and bread crumbs), which was oh-so-good, and a Caesar salad, which was decent. If I lived in Chicago, I could see Parlor becoming my go-to spot for pizza.
Having devoured our dinner, we spent the rest of the night watching more Triple D (Diners, Drive-ins, and Dives for the uninitiated). One last thing – it never did end up snowing. So, thank heavens we didn’t listen to the forecast and cancel our trip!
Day 2, Saturday: Doughnuts, Gilded Age Glamour, and Starbucks Reserve
After a surprisingly decent night’s sleep (regular readers of this blog will know that I am often plagued by poor sleep when I travel), we awoke at 9:00am well-rested and ready to face the day. Our first order of business was to find something to eat, so we popped into the hotel’s dining room to scope out the continental breakfast. Cereal cups, packets of instant oatmeal, corn syrup masquerading as maple syrup, and that particular brand of waffle maker ubiquitous to hotels and college campuses: the offerings proved rather lackluster. Desirous of something with more substance and less sugar, we retreated down the stairs and out of the building, making our way to a nearby location of Goddess and the Baker.
Unfortunately, that location (the one at 44 and E Grand Ave) was filled to the brim, with not an empty or soon-to-be-vacated table in sight. So, we left from whence we came and backtracked to the Riverfront location (225 N La Salle St), which thankfully, was nowhere near as crowded. We were able to order our food and secure a table without any issues.
As for the food, it was worth the slight hassle we endured to procure it. My Crunchy Berry Oatmeal was delicious and perfectly cooked – not at all stodgy like most restaurant oatmeal. The coffee also did not disappoint, nor did the café’s overall ambiance, which was chill and inviting.
My tasty oatmeal from Goddess and the Baker
From Goddess and the Baker, we walked a few blocks up and over to Doughnut Vault, a hole in the wall serving up freshly made, gourmet doughnuts. When I say that their doughnuts are some of the best that I’ve had in my entire life, it is no exaggeration. Their pistachio doughnut was fluffy and moist with an utterly divine pistachio flavor. The other doughnut I tried, the blackberry jelly, was also perfection, with just the right ratio of sweetness to tartness. Needless to say, my husband and I devoured both doughnuts, leaving not so much as a crumb behind.
Blackberry jelly doughnut from Doughnut Vault
Sugar infusion complete, we walked to the Driehaus Museum, a Gilded Age mansion that features both preserved rooms and exhibitions on art and architecture. The first floor houses the former. Visitors can wander through impeccably restored rooms, including the marble-clad main hall and Maher Gallery with its stained-glass dome. Walking through these rooms felt like stepping back in time – or being transported to the set of Gilded Age.
A sitting room inside the Driehaus Museum
During our visit, the upper two floors contained exhibits on Chicago’s urban renewal and the resulting demolition of numerous architectural gems within the city. These exhibits were both informative and infuriating; I couldn’t help but feel both sorrow and anger at the sheer scale of loss suffered in the name of “urban renewal.”
By the time we finished up with the exhibitions, nearly 90 minutes had passed since we had first entered the museum. So, after a quick perusal of the gift shop, we bid farewell to the 19th-century mansion and set out in pursuit of lunch.
Helpful tidbit — The Driehaus Museum is only open Wednesday through Sunday, so plan accordingly. Tickets are $20 per adult with the option to join a guided tour for an additional $5. Guided tours are on a first-come, first-serve basis and only offered at select times. For the most up-to-date tour and ticket information, please consult the museum’s website.
A quick Google search revealed that we were only a block away from a True Food Kitchen, a chain of restaurants specializing in seasonal, health-conscious food, and being that we were feeling both hungry and lazy, we settled on it almost immediately. A short two-minute walk later, we were there, and 15 minutes after that, we were seated at our table. The food more than made up for the minor wait. My Korean Noodle Bowl with tofu was flavorful and satisfying, and the hibiscus limeade with which I washed it down was zesty and refreshing. Moreover, the restaurant had a bright, modern, and sleek interior that enhanced the dining experience.
My Korean Noodle Bowl from True Food Kitchen
Fed and fueled, we decided to inject some extra pep into our step with a visit to the Starbucks Reserve Roastery, which was conveniently only a 5-minute walk away. Spanning five floors, the roastery is massive and includes a roof deck, bakery, bar, and of course, areas to buy both brewed coffee and coffee beans. Although I am generally not a huge fan of Starbucks’ coffee, I do enjoy some of their Reserve blends, including Gravitas, which is exclusive to the Reserve roasteries. Being at a Reserve roastery, I naturally ordered a cup of it, and as much as I would have liked to have sat and enjoyed it while people-watching and soaking in the modern, almost futuristic décor, I had to take it to-go due to a lack of seating.
Wall at the Starbucks Reserve Roastery displaying all of the Reserve blends
Gravitas in tow, I explored the rest of the roastery with my husband. We visited each of the floors, except for the roof deck (it had started to rain while we were inside), and once we had finished our survey of the space, we popped into the retail area to buy some beans and a mug (have you truly visited a place if you haven’t purchased a souvenir mug? 😆). All told, we spent a little over 30 minutes at the roastery.
From the roastery, we retreated to the hotel for some respite (and to dry off). A little before 5:30pm, we headed out for dinner, making our way to Planta Queen, a vegan restaurant with an Asian-inspired menu. We had not made a reservation but were fortunate enough to snag a couple of seats at the bar. Had those seats not opened up, we would have been waiting until 9:45pm for a table! (Although, if I’m being honest, I wouldn’t have waited; I’d have gone elsewhere. No place is worth a four-hour wait.)
The bar at Planta Queen
My husband and I decided to split several dishes in order to maximize the amount of food that we could try. We settled on the Ahi Watermelon Nigiri (vegan sushi with a slice of “ahi” watermelon on rice), Crispy Gyoza Dumplings, and udon noodles with shaved black truffle. Everything was delicious. The sweetness of the watermelon in the ahi nigiri was balanced out by the saltiness of the soy sauce, and the udon noodles were creamy, with a touch of earthiness and umami from the truffle shavings. The dumplings were also tasty, but the noodles and sushi stole the show. I washed everything down with the Mez-Cal Me Maybe cocktail, a blend of mezcal, passionfruit, ginger, and lime. It was decent – not the best drink I’ve ever had but also not the worst.
Plates cleared and bill paid, we walked back to the hotel, making a pitstop at Bakery Box, a 24-hour vending machine stocked with baked goods. We got a box of three macarons (s’mores, cookie dough, and Oreo) and a mini Oreo chocolate cake. Everything looked delectable, but sadly, it all proved rather underwhelming. The macarons were dried out, and the cake, while moist, was too sweet.
Box of macarons from Bakery Box
We ended the night watching Law and Order: SVU reruns.
Day 3, Sunday: Scenic Walk and Chef’s Table
Opting for a leisurely start to the day, we slept in and ambled out of our hotel around 11:00am. As we had enjoyed our previous day’s breakfast so much, we returned to Goddess and the Baker, but alas, our encore brunch was not meant to be. There was not a single vacant seat in the café, so we enacted Plan B: Léa, a French bakery. We each ordered the Lafayette Veggie, a croissant sandwich with egg, cheddar, and avocado, and it was delicious. The croissant was buttery and flaky, and the egg was cooked just right. The coffee was not too shabby either. We also grabbed a baguette and pan au chocolat to-go, and much like everything else we had sampled at Léa, they were tasty.
Lafayette Veggie from Léa
After a quick detour to our hotel to drop off the bread and pastry, we hopped on the subway to make our way to Shedd Aquarium. Unfortunately, the entry price proved too steep (it would have cost nearly $100 for the two of us), so we opted for a more budget-friendly activity – walking along Lake Michigan. We followed the Lakefront Trail, which offered stunning views of the lake and Chicago skyline.
Chicago skyline
We stopped for lunch at Sweetgreen, and it was a welcome respite. We had walked over 1.7 miles, so it was nice to kick up our feet and have a bite to eat. I ordered my usual, Kale Caesar Salad with tofu, and it was reliably average.
My solidly average Kale Caesar Salad from Sweetgreen
From Sweetgreen, we returned to the hotel for a couple of hours before setting back out to make our way to Girl and the Goat, where we had a 6:00pm reservation. We lucked out and were seated at one of the chef’s tables. We had not requested to be seated there; rather, our waitress told us she had a surprise for us before leading us to one of the two tables that directly abutted the kitchen. The view was second to none; we could see our food being made and had the opportunity to interact with some of the cooks. The only downside was that by virtue of being so close to the kitchen and its various appliances, it was a trifle hot. I mean, there was a wood-fired oven and gas stove directly in front of us. It, however, wasn’t so hot as to be unbearable.
Our view from the chef’s table
As for the food, it was among the best that I’ve ever had. They have a tapas-style menu, where you are meant to order and share several small plates. We ordered four dishes: raw oysters with watermelon radish mignonette, ponzu, and horseradish (super delicious and refreshing); chickpea fritters with goat yogurt, green chutney, and pomegranate (a scrumptious blend of savory, creamy, and sweet with a nice textural element from the pomegranate); naan served with tahini tofu and tzatziki dips (incredibly flavorful); and sautéed green beans with fish sauce vinaigrette and cashews (amazing). I washed everything down with a locally made cider that had hints of clementine, cinnamon, rosehip, and hibiscus – as with everything else I’d consumed that evening, it was delicious.
Naan with tahini tofu and tzatziki dips
After about 90 minutes, we departed from Girl and the Goat and took the metro back to our hotel. We watched a couple of Law and Order: SVU reruns before calling it a night.
Day 4, Monday: Homeward Bound
Fortunately, we didn’t have an early morning flight, so we were able to wake up at the reasonable hour of 9:00am and pack up anything that we had not already packed the night before. We grabbed a couple of egg sandwiches from an Einstein Bros. Bagels around the corner for a quick brekkie, and once we had scarfed those down, we called an Uber to the airport. A few hours later, we were back home in our Boston apartment.
It was a wonderful trip, and I am eager to return to Chicago and continue exploring it.
Summing it up: The 3 Wheres
Where We Went
River Walk
Millennium Park
The Bean (Cloud Gate)
Art Institute of Chicago
Driehaus Museum
Starbucks Reserve Roastery
Lakefront Trail – Grant Park
Where We Stayed
Kinzie Hotel
Where We Ate
Breakfast
Yolk
Goddess and the Baker
Léa
Einstein Bros. Bagels
Lunch
Just Salad
True Food Kitchen
Sweetgreen
Dinner
Parlor Pizza
Planta Queen
Girl and the Goat
Dessert/Coffee
Doughnut Vault
Bakery Box
And that does it for this Chicago travel guide — I hope that you found it helpful! As always, if you have any questions, feel free to ask them in the comments section below!
