An Attempt to Eat Our Way Through Chicago

Landscape view of the Chicago skyline

A rare peek at the sun earlier during the week.

Chicago welcomed us with overcast skies and a light drizzle, eventually building up to a torrential downpour by nightfall. We spent our week with J’s cousin Rose, and her husband, Rick, both of whom live on the second floor of a creaky and endearing split-level home in Bridgeport. They told us this house survived the Great Chicago Fire because the neighborhood was located on the other side of the river. The noticeable slant in the floor and the ancient squeaks from the weathered wood revealed the house’s maturity upon walking to the guest bedroom, something Rick humorously pointed out to us.

A living room with a plaid couch, rug, Christmas lights, and a dresser.

Rose & Rick’s illuminated home

Chipped cymbal in the foreground

Rick’s drumset in the front room

A frost advisory marked our second night in Chicago once the rain subsided at around 12am. Rose and Rick both worked late hours, so we stayed in that night and waited eagerly until they got home. The weather gradually improved afterwards, and we were able to spend more time outside. When we returned from exploring the city, we’d still wait for Rose & Rick to come home from work to walk to Maria’s for a few drinks, or talk until almost sunrise.
A view of Navy Pier from the Chicago River

Navy Pier from the Chicago river


Asrai Garden | This charming floral boutique also sells home decor and jewelry. I accidentally got some fragrance oil on my hands while poking around the cosmetics, and I found myself sneaking whiffs of its mossy, wooden warmth until it was time for dinner. I regret never getting the name of it.
Quimby’s | Quimby’s specializes in independent press literature. Their zine and selection is amazing, but if you need to get your fix of Cereal, Monocle, or even Lula, they have small press glossies, too.
Myopic Books | three levels of used books and a reading area on the top floor make this Wicker Park staple a bibliophile’s happy place.

Food splayed on a table at Little Goat Diner

Little Goat Diner


(apparently we did more eating and drinking than shopping)
The Winchester | This airy, illuminated establishment in Ukranian Village sources their ingredients locally. Don’t be deceived by that green pozole. It was both delicious and filling.
Chicago Waffles | Their bacon and chicken waffles are a steal at $4.99. I stuck with the mainstay of Belgian waffles, which were delicious in their fluffy, vanilla-scented, simplicity.
The Duck Inn | A moody dining hall centered around all things waterfowl—well, most things, at least. I ate the roasted porcini mushrooms with toasted farro, and was surprised to find popcorn in my dish, which added a nice crunch. A few friends wanted to try their shrimp & duck lumpia, but they were out. Of course. Everyone loves lumpia.
Dusek’s | This Michelin Star recipient has an expansive beer menu. While I tasted the my companions’ yummy brews, I saved my appetite for their spring risotto. Creamy 1 hour egg and risotto meets savory, crunchy ramp granola and green asparagus. The crowning touch was that tiny bite from the habanero sauce.
Little Goat Diner | The sister restaurant to Top Chef winner Stephanie Izard’s Girl and the Goat serves modern takes on comfort food. Plus, breakfast is served all day. In my attempt at eating a light dinner, I ordered tempura mashed potatoes and the sweet onion soup—nope, still overstuffed.

Coffee, green pozole, roasted potatoes, egg and avocado toast, and a burger at The Winchester in Ukranian Village.

Breakfast at the Winchester in Ukranian Village

Lou Malnati’s | Because deep-dish pizza. This establishment is all over Chicago, and it’s certainly one of the more touristy things to eat while you’re up there. The line was a little long, but worth it; just don’t forget to carry some Lactaid.
Monteverde Restaurant and Pastifico | Monteverde practically runs on flour power, making some of their pastas in-house. I had their gnocchetti sardi, and the smooth, house-made ricotta complemented the acidity in the grated tomatoes. They take freshness seriously.
Nana Organic | Nana is another establishment sourcing organic, local, and sustainable ingredients. Veggie- and vegan-friendly.

Soy chorizo, black beans, tofu, and tortillas at Nana Organic in Bridgeport

Breakfast at Nana in Bridgeport

Oiistar | I was really starting to miss eating rice, so Rose took us to this spot in Wicker Park. Sit by the bar and you’ll notice an enormous glass carafe of soy sauce, which I want to say is about four gallons (I forgot to ask the bartender). Oiistar’s bao-inspired buns are awesome, but I was convinced they tasted even better the following morning with all those flavors mingling a little longer.
Pleasant House Bakery | Pleasant House’s humble exterior is easy to dismiss, but walk inside and give their pies a chance. Crispy, flaky little pockets with warm, creamy goodness inside. It’s a lovely pie both inside and out. Have their triple-fried fries and stop by Maria’s next door to grab a beer to enjoy with your meal . (It’s BYOB at Pleasant House)
Lincoln Park

Lincoln Park


Bridgeport Coffee | Bridgeport has relationships with their growers, allowing them to get their beans directly, roasting them in-house, and ready to offer to the rest of us. We got a bag of their Santa Josefina Natural, which tastes creamy, smooth, and a little like honey.
Punch House | Just a floor beneath Dusek’s, we shared a carafe of the Crillon Paris with a friend and played card games after enjoying dinner upstairs at Dusek’s. I found myself fishing for the bits of heirloom apple in the empty carafe once the punch was consumed. Careful, it’s dangerous stuff. Also, don’t forget to grab some chalk and leave your mark on the walls on the way to the restrooms.
Maria’s Packaged Goods and Community Bar | Enjoy some stiff drinks and if you’re lucky, they might have an episode of Speed Racer playing from a projector in the back of the bar.
The Barrel | A dive bar with cheap, delicious cocktails. Sometimes they have live music.

A view looking down the Chicago River

A view of the Chicago River from one of the architecture boat tours

Tune in next week for part two of the trip. We’ll talk about things to see in Chicago.


  1. Lani

    Nice to read about your visit – we ate our way through Chicago as well and enjoyed Monteverde and Oiistar for the same reasons that you described. We will definitely go back and try some of the other places you listed. Were you able to listen to live music or hear Rick play?

    • We did listen to a little bit of live music, which was AWESOME, but sadly, we didn’t hear Rick play. Ate Rose told us you guys had some frost when you were up there!

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