I haven’t been super keen on visiting anywhere in the continental US in the last few years. It’s not like I don’t enjoy a good US city, I’m just a little bit more partial to international travel. That said, I think there are some US cities that are just too exciting to miss. So when the opportunity presented itself for me to visit Chicago, I absolutely leapt on it.
Chicago is just an effortlessly cool city. It’s massive and integrated, but it has managed to keep an old school neighborhood vibe with no pretentiousness. There’s nothing worse than a beautiful city with rich culture and excitement having its pulse ruined by a gaggle of dickheads shielding your view of its splendor. And I can say that definitively because I lived in LA for 3 years. But I digress. Chicago is great.
I look for a few things when I travel; Food, walkability, and options. I have ADD and an appetite for things I’ve never (or have rarely) experienced before. I realize that the idea of a vacation for most people involves beachside relaxation and all inclusive buffets. But the thought of getting on a plane for 7 hours to to go lounge in a hammock and eat heat lamp warmed scrambled eggs next to a beach sounds about as appealing to me as county jail. In fact I’ve been to county jail, and I’d choose it over Cancun any day. At least county jail was unpredictable and the ride there was free. When I’m out of town I want chaos, greasy street tacos, and sensory overload.
Chicago is spread out with plenty to do in any area you find yourself. You can visit a different country’s kitchen table every night. You can see a Broadway show or a DJ. Or you can easily spend $1000 on a tasting menu. So with all that being said I think I’ve put together a pretty good list of places you need to eat and drink when you visit Chicago.
1.Pequod’s Pizza
I’d be remiss if I made a visit to the Windy City without paying homage to one of their most respected pizzerias. Say what you want about deep dish, but if anywhere is doing it perfectly it’s Pequod’s. Imagine the original Pizza Hut recipe on anabolic steroids. Their perfect buttery crust is absolutely charred to a crisp in a pan and topped with tangy sauce and sharp cheese. The presentation is borderline ugly. But the taste is nothing short of special. The caramelized cheese crust creates a deafening shatter as you sink your teeth in. The sauce and cheese combine to create a delicious, mouth burning magma. It’s a sensory overload. If you don’t feel dirty after you ate Pequod’s, you didn’t do it right.
2-3 hour wait for a seat. Get takeaway if possible. Your hands should burn when you pick up the slice to get the full experience.
2. Fatso’s Last Stand
I’m not breaking new ground with some of these suggestions, simply reiterating that sometimes the hype is real. Fatso’s is not only worth a trip, but you may want to come extra hungry so you can try a few other things on the menu. The char dog has everything you could ask for. A pillowy soft poppyseed roll, a crunchy charred hot dog, and comedic amount of “dragged through the garden” accoutrements. The classic Chicago hot dog usually includes mustard, onion, celery salt, tomatoes, pickles, and hot peppers. Some also add French fries. I had a few hot dogs in Chicago. Fatso’s hot dog stood out because it was big enough to satisfy the craving but not so big that it made you feel awful. You have to struggle to get a bite of everything, but after one you debate ordering a second to round out the edges.
Don’t get takeaway. Sit at the restaurant and enjoy.
3. Firecakes
If a city doesn’t have a good donut shop, it’s not a real city. I zeroed in on Firecakes for its seasonal specials and focus on old fashioned donuts. It’s hard to act like I can be discerning when it comes to deeply fried, sweet dough glazed in sugar. But firecake’s donuts stood out with their dense, buttery texture, and light exterior crunch. I made two trips to the Lincoln park location. On round one I ordered the carrot cake donut which would make any spiced cake connoisseur swoon. Most importantly, the recipe omitted the raisins. On my second trip I opted for the pistachio old fashioned. It was uniquely nutty (go figure) while holding true to a traditional sour cream donut mouth feel. Kind of like an upscale hostess old fashioned. I would describe the flavor as almost artificial in the best way. The donuts were among some of my favorite in any city. Well worth the walk and the trip.
The shop is small with limited outdoor seating. Tons of donuts to choose from when I visited. Get a seasonal flavor and an old fashioned and go sit in Lincoln park to enjoy.
4. Dear Margaret
I limit myself to two restaurant reservations maximum per vacation. This way I can be spontaneous and make the trip more exciting. It sounds easy on paper, but in practice it makes the final choice seem utterly existential. I spend hours combing through menus and reviews. I don’t have any specific criteria for which establishments I end up picking. It typically ultimately comes down to which one is doing the most exciting things with food, and how unique the experience will be. If there’s any restaurant doing exciting things with food and boasting a unique ethos, it’s Dear Margaret. It’s menu focuses on traditional French Canadian food, which frankly I didn’t know existed. But any menu with a charcuterie section has me sold. We began the meal with a fresh baguette, Valdeon Blue cheese, and house cultured butter. I’m not being hyperbolic when I say that good bread has the power to make life’s difficulties seem trivial. I felt like I was being reborn with each bite. The sharpness of the cheese and softness of the butter teamed with that chewy submarine of bread was nothing short of sexual. Don’t be weird. Just order the bread. The steamed asparagus was light and simple and served as the perfect intermediary to the main course which was the aged duck breast. Duck is polarizing because if you cook it wrong it sucks. I’ve heard the key to good duck is an aging process. If this dish is any indication of that, I want all of my duck breast’s to be on the edge of pure rot before they hit my plate. Served skin on over white rice, each little piece was like a fat bomb delivering perfect flavor to every corner of my mouth. It always blows my mind how a dish with such basic ingredients can just blow you away. This is what sets a restaurant apart from any other fine dining establishment. The key is to use culinary technique simply and let the ingredients do the talking. Dear Margaret did not disappoint.
This is one of the hottest tables in Chicago. I have no doubt DM will join the ranks of the Michelin Star elite in the city. Until then they are BIB gourmand, and a reservation is a must.
5. Superkhana International
You know what? I love brunch. Sue me. At least I can admit it. Very few things speak to my sensibilities more than a post noon runny egg and pancake. But it’s so easy to find a basic brunch spot. During my trip, I was after something completely unique. Superkhana almost didn’t make my list. While the food was delicious and the service was great, the whole vibe kind of screams elitist hipster. The bun omelet and dosa hash are worth the trip alone. A giant fluffy egg omelette topped with cheese and wedged between buttery toast? I could eat that in anywhere and be happy. But the place was just a little bit cold. That’s not to say it wasn’t great, it was absolutely worth the trip. But it could stand to involve some more smiles.
Again this is one of the hottest tables in Chicago. For dinner or brunch make sure to grab a reservation. Order a cocktail , too. I had the “Big Dill” and it was a revelation.
Honorable mention:
Paulie Gee’s Logan square
Paulie Gee’s is a quintessential NY slice giant. The man himself is a legend of the craft and has made outposts throughout the country showcasing his perfect triangles and squares. I know NY style is not a Chicago thing (obviously) so that’s why it’s an HM not a list maker. But I would feel like a sinner if I didn’t mention this magic factory somewhere. It’s a hole in the wall. I have read so much about Paulie Gee and his legacy and was so eager to get a crack at one of these slices. I opted for the “Logan Zaddy”. It’s a pizza with ricotta dollops, hot honey, pepperoni, mozzarella, and parm. After taking my first bite, I just can’t explain how happy I was. It was like trying pizza for the first time. If perfect pizza exists, it’s created at Paulie Gee’s. More impressive to me is the fact that he’s been able to franchise and maintain the quality. Great low key staff and vibe, also. Get a slice, sit and people watch. I went back two days in a row.
So that’s it. My first travel log. Obviously this wasn’t the only good food I had on the trip. Make some time to check out Stan’s doughnuts, Hoosier pie, and Fado Irish pub as well. If you have time, stop at the spots I suggested. But the important thing is to explore this city and just eat as much as you can. Just like any other city. Enjoy every cultural, greasy, beautiful bite. You’ll be hard pressed to find any shitty food in Chicago if you’re out for something tasty. Until next post my friends. Thank you for reading.
