A Foodie’s Guide to Chicago: 16 Essential Eats

When a family holiday recently brought me to Lake Michigan, I took the opportunity to tack a few days onto the end in Chicago to do some eating. Because why not? I was lucky: I had the local knowledge not only of an ex-colleague from back in day at Mega Corp, but also of several of Mr Foodie’s cousins who live there. I didn’t need to do a lot of research, because these guys had got the Chicago food scene covered. All I had to do was sit back, relax, and undo that top button…

16 Must-Eat Meals in Chicago, Illinois

1. Vienna beef hot dog at George’s Hot Dogs

Also known as a “Chicago Dog”, the Vienna beef hotdog seems to be most Chicagoans’ fast food of choice. Crucially, the sausage needs to be made of beef, the bread needs to be a steamed white bun, and the whole thing needs to be topped with seven condiments: mustard (never ketchup!), relish, tomato, onions, jalapeno peppers, and one of those giant pickled gherkin things you see on top (you can use it to squish everything else down). I tried this at the over 50-year old George’s Hot Dogs in Bucktown, thanks to a food tour I took with Chicago Food Planet. I then tried another at Al’s Beef (more on that below) – both were pretty damn good.

2. Deep-dish pizza at Lou Malnati’s or Pizano’s

When I first came to Chicago in 2011, I tried the deep-dish pizza at Lou Malnati’s. The next time, I went to Pizano’s. Probably because I’m an Amsterdammer, I couldn’t tell the difference – they were both indulgently wonderful. Despite the name “deep-dish”, the crust is actually deceptively thin and almost pastry-like; it’s the filling that’s deep – thick with cheese, tomato and sausage. But I hear the locals rarely eat deep-dish pizza because they’re too big and take too long. Which brings us onto…

3. …Thin-crust pizza at Piece

If you want to eat like a local, thin-crust pizza is where it’s at. If you’ve spent any time in Italy, though, prepare to be appalled. Thin-crust pizzas in Chicago are nothing like those of their European cousins. Where in Rome you’ll want to order a straight margarita (why make a simple thing of beauty unnecessarily complicated?), at Chicago’s Piece you can expect toppings like BBQ sauce, jalapeno peppers and even mashed potato. I know – mental.

4. Italian beef at Al’s Beef

This is proper hangover food. Trust me. It’s essentially a sandwich that involves thin slices of beef, dripping in their own jus, stacked into a soft bun (to soak up the juices) topped with a whole heap of hot, spicy, pickly goodness. Once again, it bears no resemblance to anything you’ll ever eat in Italy. But don’t let that get in the way of a good sandwich. Al’s Beef might not be much to look at, but it’s been voted the #1 place in Chicago for Italian beef, and purveyor of one the top five sandwiches in America. So there.

5. Mexican food at Topolobampo

Any visit to the US is always a great excuse to eat decent Mexican food, and Chicago is no exception. I was lucky enough to be taken to Topolobampo – one of Rick Bayless’s empire of restaurants. This one serves upscale contemporary Yucatán food. The trio of ceviche was standout (be sure to get a margarita to go with them), as were the main courses we tried: tinga poblana tostadas, and wood-grilled quesadillas stuffed with beef short rib and a charred tomato salsa.

6. Fusion tacos at Velvet Taco

If you can’t decide what you want for dinner and aren’t a purist when it comes to tacos, I’d strongly recommend checking out Velvet Taco. They fill their corn tortillas with everything from buffalo chicken and blue cheese dressing to falafel with tahini. Their tuna taco doesn’t even come in a corn shell – it comes wrapped in lettuce. Like I said: not one for the purists, but highly delicious nonetheless!

7. Sushi at Union

I also get quite excited about sushi when I go to the States. Not because you can’t get decent sushi in Amsterdam, but because it tends to be a rather formal and pious in comparison to its flamboyant American sister. Both have their place, but U.S.-style sushi is just – well – fun. I spent an ungodly amount of money on the stuff at Union – but it was worth it. I can’t really begin to describe what was in all those rolls (apart from the fact that some of them were filled with black rice instead of white – whaaaat?!), but just take a look at the photo collage – it’s got Mouth Party written all over it.

8. Ramen at Ramen-san

Regular readers will know I’m a tad obsessed with ramen in Amsterdam, so it’s no surprise that I decided to check out a ramen restaurant while in Chicago as well. Ramen-san came highly recommended, and with good reason. I tried a miso-based broth with spicy pork, sesame, spring onions, seaweed… plus a side of kimchi because I can never resist it. But my friend’s chicken broth with fried chicken and corn was a slightly more American but no less delicious noodle soup. Just make sure you schedule a long stroll along the Riverwalk afterwards…

9. Nine-course menu with attitude at Schwa

It would be easy to miss Schwa, a tiny restaurant with no signage on the fringes of Wicker Park. But you’ll need a reservation at one of their six tables if you want to eat the nine courses of culinary craziness on offer. You’ll also need to bring your own booze – but don’t expect any guidance about wine pairing before you arrive. Nor, for that matter, directions to the toilet. It says it’s for employees only, and you’ll wander past the kitchen trying to find it – if you’re lucky, you might do a shot with a chef en route. Suffice to say that dinner at Schwa is the least “fine” fine-dining experience you’re likely to have. But the food – well, that’s a different matter. Think langoustine tail, set in a ball of jellied Gewürztraminer, served in a spoon that you then mix into a warm umami-rich broth to create your own langoustine soup. Or rich parmesan with dried banana, nori brittle and manuka honey. Or, perhaps my favourite: a tight roll of pappardelle pasta with summery peas, ramp (a local species of wild onion) and uni-koji (nope, I’d never heard of it either). Schwa is a memorable experience – both for reasons you’d expect and for reasons you wouldn’t. Just don’t be intimated by the chefs – it’s all part of the act…

10. Michelin-starred dining at Goosefoot

With a little more polish but no less heart than Schwa, dining at Goosefoot is made for a special occasion. The husband and wife team (he’s in the kitchen, she’s front of house) will take you on a culinary and cultural journey through seven courses of decadent deliciousness. The night we were there, the theme was Woodstock, and everything from the music to the décor to the dishes screamed flower power. As you can see from the collage, there were plenty of edible blooms on the plate, as well as creative takes on corn chowder and truffle pasta. Goosefoot is also a BYOB, but they have a wine store next door and you can pick from a list of wines that they’ll deliver straight to your table with no corkage fee. It’s no wonder that Chris and Nina Nugent have a Michelin star.

11. Lunch at Aster Hall

Located on the top two floors of a chic shopping mall on Chicago’s Michigan Avenue, Aster Hall is an oasis of calm that’s perfect for resting and refuelling in between shopping. And while it’s a food court selling meals from a range of separate stalls, it’s unique in several ways… Firstly, ordering happens from one central computer system, so if the person you’re eating with wants sushi but you want a burger, you can still order from the same place at the same time and pay together. Secondly, while the fifth floor is a good spot to sit at a high table and people-watch while you eat your lunch, the sixth floor has comfy couches, lounge lighting and chic design – all of which make you feel more like you’re eating at Soho House than a food court. The day I visited I felt the need for some clean eating, so I tried this salmon poké bowl with plenty of crunchy veg and a fresh, gingery dressing. It cost $13, but it was substantial enough for a filling lunch, and the use of the lounge was just what I needed to break up a busy day. Perfect for work or pleasure.

12. Gnocchi at Franco’s Ristorante

For some inexplicable reason, Mr Foodie claims not to like gnocchi which means I hardly ever get to eat it. So when the cousins took us to a Chicago-Italian restaurant – Franco’s – I jumped at the chance to order their famed homemade gnocchi. It was simple, cheap and cheerful, but well worth every cent. Order a glass of house red wine to wash it down, and sit at the bar for great people watching.

13. Bellinis and cookies at Restoration Hardware

It may sound like a furniture store (and indeed it is a furniture store), but Restoration Hardware is also home to one of the most elegant dining and drinking establishments I think I’ve ever visited. Bedecked with chandeliers and fountains, it might not seem like the obvious place to take a seven-year old. But they serve the most amazing chocolate and sea salt cookies (for the kids) and pastel-hued, grown-up bellinis (for the adults).

14. Hot chocolate with marshmallows at Mindy’s Hot Chocolate

As regular readers will know, I don’t have much of a sweet tooth. I made an exception, however, for the hot chocolate and home-made marshmallows at the eponymous Mindy’s Hot Chocolate in Bucktown. Chef Mindy Segal has won a bunch of awards as a pastry chef, and it’s clear why: she makes quite simply the thickest, richest, tastiest hot chocolate that’s ever passed my lips. And the marshmallows are like dreamy puffs of raw meringue – heavenly.

15. Cocktails at Three Dots and a Dash

Tiki bars seem to be enjoying a revival in the US, and the original and best is at Three Dots and a Dash. It is not, however, easy to find. Wander down an alley off W Hubbard St (never mind the fact that the address says N Clark St) to find an unmarked entrance flanked by skulls. Once inside, go down the stairs to the basement where hidden treasures await… I only ordered one drink (the signature, presumably – its name was the same as the bar’s) and left considerably tipsy. You have been warned.

16. Liquor at a Chicago “slashie”

I only discovered the concept of a slashie on my most recent visit to Chicago, so for those unfamiliar with the term, we’re talking about a liquor store slash bar. Yup, some of the city’s oldest and grungiest liquor stores now stay open till late in the night serving every weird and wonderful bottle of the hard stuff you can imagine to equally grungy patrons. At Rite Liquors in Wicker Park, I tried jalapeno whiskey (surprisingly good), bison-grass vodka (as good as I remembered it from Poland) and Gentleman Jack (which tasted like paint stripper). You win some, you lose some. There is photographic evidence of my slashie experience, but it’s not fit for public viewing. My advice? Try it for yourself…

This article was first published in November 2015, but was updated in September 2018 and September 2019 following later visits to Chicago.

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