Eating our way around Chicago

Piero and I just got back from a quick 4-day trip to Chicago and it was AMAZING!! For those who haven’t been before, it is a really lovely city, very liveable (in the downtown specifically). There’s so much interesting architecture (old and new), and some really expansive and beautiful parks, particularly around the waterfront. I just kept saying “WHY CAN’T TORONTO HAVE NICE THINGS???” (For instance, in Chicago, you can pay for public transit with a tap debit card. What the what???)

Besides walking around, gawking at all the pretty things, we mostly stuffed ourselves with food all across the city. Basically, how I travel is, “We should go to this neighbourhood because apparently there are good tacos there, and then this other neighbourhood because they have pierogies.” Etc. Piero just shakes his head and follows along.

Dinner on our first night was at Table Fifty-Two, where the cuisine is New American twists on Southern classics. The chef was apparently Oprah’s private cook for a number of years. In a beautifully renovated mansion in the upscale Gold Coast neighbourhood, a bit north of the downtown Loop, Table Fifty-Two felt intimate, decadent, and friendly. 

I started with the spiced shrimp in a tomato stew with creamy, cheesy grits. My main was crispy fried catfish topped with crunchy strips of fried jalapeno. Piero started with the rhubarb and pig ear (yes, pig ear) salad, and then the duck confit. We shared some garlicky sauteed collard greens, and I nursed a ridiculously strong and delicious bourbon Manhattan the whole meal. I have no photo evidence because I’m weird and get freaked out about seeming like a “rube” in fancy restaurants. So, alas, I didn’t whip out the camera. No lie, it was probably one of the best meals I’ve ever had, photos or no photos.

Likely our second-best meal in Chicago was at Taqueria Los Comales 3 in Pilsen, which offered basically the direct opposite atmosphere of Table Fifty-Two in terms of decor. But, costing roughly one-tenth of our dinner at the other, our full table spread of beef and chorizo tacos (Piero’s), poblano gordita, and avocado tostada (mine) was incredibly good. Everything was fresh, flavourful, and authentic.


I believe this was the day that all of our meals were fried. We started out at Do-Rite Donuts, on Randolph in the Loop. They make all kinds of unique gourmet donuts (many GF options as well). I had the carrot cake donut with cream cheese icing, and Piero had the chocolate eclair. Best donuts ever? Best donuts ever. (Piero regretted not getting the bacon donut for the rest of the trip. Such unwise choices he makes.)

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Whilst wandering around Millenium Park, we stumbled on Terzo Piano, a terrace restaurant atop the Art Institute of Chicago with a lovely view of the park and Loop. I promptly ordered a Bloody Mary (because it was 11:30 am and it is made of tomato juice so that is basically a healthy breakfast smoothie). We snacked on the crispy eggplant fries with tzatziki dip. (This was the day when all our meals were fried… It’s good to be consistent.)

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Beyond delicious food offerings, Chicago is wonderful for coffee options. SO MUCH COFFEE. First stop was Ipsento in Bucktown. The Ipsento Latte is no ordinary beast: it is a wonderful blend of rich espresso with creamy, frothed coconut milk, honey, and a dash of cayenne pepper. Piero and I could not stop raving about this amazing creation (which we have now recreated 3 times at home since returning to Toronto – never as delicious as the original, though). We both also got the Ernest Hemingway breakfast sandwich: smoked salmon, capers, egg, and cream cheese on a flaky croissant. Mmmmmm. Basically, for the rest of the trip, we just kept lamenting that Ipsento was all the way in Bucktown in the West and so we would never end up going back. (Our apartment was in the South Loop, right near the downtown area.)

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Another wonderful coffee stop was Intelligentsia, which is just painfully hipster but has quite good cappuccinos and lattes. I think their drip coffee is the big draw, as they have all these chemistry lab-looking contraptions for different drip brewing processes. (See their website for a better picture of what I’m saying). We also had a few pastries here – the morning roll was deliciously flaky, but the canele was disappointing (especially as we had the real deal in Bordeaux last year and can now be snobs and call them canelés and turn our noses up at inferior American ones that are missing accents aigus) .

DSCN1587Summary: Go to Chicago, if you have not! Eat all the things. The end.


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