Field Report: Chicago

Cole Kennedy
This There That
Published in
5 min readApr 7, 2016

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Last weekend, both Andrew and I were in Chicago. It’s actually the second time in the past few months that we’ve accidentally been visiting the same city at the same time, but it’s the first since we launched the This There That website. We took advantage of our renewed vigor for exploring cities to try out as many restaurants and bars as we possibly could in 72 short hours, so that we could confidently give you our three best recommendations: one classic, one curveball, and one cocktail.

The Classic

Our previous recommendations were based on (perhaps outdated) experience, extensive research, and second-hand knowledge from our network of friends. The classic pick was The Gage, a gastropub on Michigan Ave right across from Millennium Park. I first went there a few years ago while visiting Chicago around Christmastime; it was freezing cold and my father and I wanted somewhere cozy (but not dingy) to grab a drink after dinner.

While the Gage was a great pick that evening, Andrew and I came to the conclusion that a pub serving an admittedly stellar fish and chips didn’t really make the cut for somewhere we’d tell our friends about if they were travelling. The classic pick is meant to be comfortable, but not mundane. So Andrew went to dinner at Longman & Eagle, a cozy-yet-trendy spot just a block away from Logan Square. The menu actually opens with a variety of ambitious small plates, stuff like bone marrow with bacon-shallot jam and “duck-in-a-jar,” that might’ve pushed the menu into our edgier Curveball territory.

New American is a dynamic genre, though, and when Andrew looked at the entrées he was sold on Longman & Eagle being our go-to Classic in Chicago. They’re serving a locally-sourced and farm-raised beef burger, a Wild Boar Sloppy Joe, housemade potato gnocchi; frankly, there’s not a single dish that doesn’t look divine. We think you’ll find something to love.

The Curveball

Cheeseburger and Golden Fries at Small Cheval

Our original Curveball was the fairly recent Small Cheval. It made a huge buzz after opening in the trendy, young Bucktown neighborhood. It perfectly hit our curveball criteria: a bit off the beaten track where you wouldn’t expect to go for a business dinner, and a place that has palpable uniqueness. Both Andrew and I made sure to hit this burger joint (which is actually the sibling to Fulton Market’s Au Cheval, itself a destination if you’re willing to wait up to three hours for a seat) on our most recent trip, and it did not let us down. In the past, I’ve said Butcher & the Burger in Chicago’s Lincoln Park neighborhood is my favorite in the world, but now I’m conflicted.

The menu (and the Fernet) at Small Cheval

Either way, you owe it to yourself to visit. Order a house-style cheeseburger, golden fries, a chocolate shake spiked with Bailey’s, and after all that, finish off with a shot of Fernet. We’re happy keeping Small Cheval around as our Curveball, despite it being a straightforward burger joint.

The Cocktail

The last pick might’ve been the most challenging. Chicago is quickly becoming one of the best cocktail cities in the country, so trying to find just one to attach our seal of approval to was tough. Our initial set included the Milk Room, at the tremendously cool Chicago Athletic Association Hotel, but at only eight bar stools and a long waiting list for reservations, it’s just not the right place to recommend for a friend (though it should still be on your personal to-do list).

We tossed around Avec and its sister Blackbird, but both suffered the same problem we expected of Milk Room: simply too much demand for a small space. On Saturday night, Andrew and I hit different spots; I went to Broken Shaker in the Freehand, and he went to Moneygun. While Broken Shaker made our set for Miami, the one in Chicago was a hair too quirky for the This There That taste profile. Moneygun, on the other hand, was right on the money. It hit the target. Bullseye. (Okay, fine, I’ll stop.)

Moneygun delights from their motto onward: mounted on the subway tile bar, just above the polished metal taps, is a sign reading, “Pleasing you, pleases us.” Simple, but effective. Their cocktail list eschews the current trend of putting some unique spin on a drink and giving it a clever name, and focuses on those classics. An Old Fashioned, a French 75, a Dirty Martini, hell, even a Cosmopolitan. Clearly, they don’t care about trends; they care about good cocktails and giving the people what they want. This is where you want to end your night.

It’s always a delight to explore a city, even one like Chicago where Andrew and I have both spent so much time. We get a real kick out of doing this sort of reconnaissance for you, so that when you land at the airport, you know there are three perfect recommendations waiting for you. We’re eager to share more dispatches from our travels, and give you further insight into our process. We want you to know how much we care about these choices, so that you know you can trust us. Until next time (perhaps we can get Marshall to give us the lowdown on Atlanta), enjoy yourselves.

Visit This There That to find three perfect recommendations in every city, hand selected by Andrew, Marshall, and Cole.

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