To get to be one of my favorite cities in the US, you’ve got to be one of my favorite places to eat. Chicago certainly is that, which is the main reason I keep going back—as a Cleveland sports fan, it certainly isn’t for their wretched baseball teams. I also go to visit some good friends, but this isn’t an article about my nine best friends in Chicago; I’m talking about food. So if you do go to Chicago—and I pray that you do—go hungry. There’s a lot to eat.
While the huge building in the middle of downtown may scream “tourist trap,” Portillo’s is a great one-stop shop for most of the Chicago food you need to experience. They have a solid Chicago-style hotdog, which includes mustard, relish, celery salt, onions, tomatoes, a pickle spear, and peppers (and no ketchup, just the way god intended). Also not to be missed is their Italian beef sandwich, topped with giardiniera (basically a chunky Italian relish) and either drizzled with gravy or “dipped”—completely submerged in the gravy. I suggest the latter. 100 W. Ontario, Chicago, IL 60610
2. Pequod’s Pizza
You’ll never get a full consensus on where to go to get the best pizza in Chicago, or if you even should eat the pizza in Chicago. A lot of east coasters balk at the pies, but I prefer pizza in Chicago—if you want a meal, that is. If you just want a little snack, stick with your thin New York pizza. In any case, you can hit any of the big names: Pizzeria Uno, Lou Malnati’s, Gino’s East, Giordano’s, etc. But I’ve found, and have a few locals backing me on this, that Pequod’s is one of the best places to stop in the city. It’s a little out of the way from downtown, but airier crust and caramelized cheese on the sides will make the trip worthwhile. 2207 N Clybourn Ave, Chicago, IL 60614
While any of the Rick Bayless empire would be worth stopping into, XOCO is a little less upscale and a bit more traveler-friendly if you’re just breezing through. The fully-dressed guacamole (with spicy roasted poblano, chicharrón, grilled onion, smoky bacon, tomato, queso fresco, and pumpkin seeds) is worth snacking on while you wait for your order, and their caldos (hearty soups) will revive you from the worst of drunken nights (I’ve seen it first-hand). The real star, though, and frontrunner for my favorite sandwich of all time, is the torta ahogada. Pork carnitas, black beans, and pickled onions on crusty bread and sitting in a tomato-arbol chile sauce—I would walk to Chicago to eat this sandwich again (and have eaten it on three consecutive trips). It comes in mild, medium, or hot, but I would stick to mild. 449 N Clark St, Chicago, IL 60654
Another one of my long-time favorites, Avec is a must-visit for a casual spot with top-notch food. While the menu will change, the chorizo-stuffed, bacon-wrapped dates (baked in a delicious spicy tomato sauce) should always be there—and should always be ordered. Probably two or three times. The oven-roasted cauliflower is surprisingly good, and the braised lamb neck was excellent. Be sure to go hungry, and be sure to plan some time to walk off your meal (this is very important). Our bartender asked us if we wanted a half order of the cauliflower and, taking it personally (he doesn’t think I can finish an entire cauliflower dish?) I of course opted for the whole. I probably should’ve gone with the half order. 615 W Randolph St, Chicago, IL 60661
5. The Purple Pig
As the final meal of our last trip to Chicago, we couldn’t have asked for a much better note to go out on. With a tagline of “cheese, swine, and wine,” it’s hard to imagine The Purple Pig being bad. In addition to the wine, they had a solid beer selection, and the Mediterranean-style shareable plates were all hits. The biggest hit was probably the salt-roasted beets with whipped goat cheese and pistachio butter, while the beef tendon chips (puffed out like huge pork rinds) with salt and vinegar made an excellent snack. We definitely left Chicago on a high note. 500 N Michigan Ave, Chicago, IL 60611
Ever since my trip to Peru in 2014, Peruvian food has been on my radar. When I learned Gaston Acurio had a restaurant in Chicago, I had to swing by—and was glad I did. Tanta‘s pisco sour was delicious, the chicha was refreshing, and the lomo saltado brought me back to Cusco. I also loved being able to re-experience the huge corn that is so popular in Peru, which showed up in both their beef heart dish and the cebiche we ordered. We went for lunch on a weekday, so the place was almost empty, but I would go anytime. The food and drinks are well worth a stop. 118 W Grand Ave, Chicago, IL 60654
I know there’s nothing very “Chicago” about Eataly, but if you’re staying in the River North area, it is incredibly convenient. There are a variety of restaurants and bars, as well as shops for everything you can imagine. Beer, wine, fresh pizza dough, high-end Italian food products—whatever you need, Eataly will have it. What we used it for, however, was the coffee. Being a scant half block from our hotel, each day in Chicago began at the coffee counter at Eataly (and some ended there), sampling the various styles to either jumpstart our day or to wind down. I wouldn’t go out of my way to visit, but if you’re in the area, definitely swing in. 43 E Ohio St, Chicago, IL 60611
I’ll be honest: Alinea is expensive. It is, however, worth the expense. As the only Chicago restaurant with three Michelin stars, it is often ranked among the top restaurants in the world. If you’ve seen the episode about Alinea on the Netflix series Chef’s Table, you’ll know what kind of treat you’re in for—food that looks like something else, food you didn’t know was at your table, dessert that could be classified as art—the experience is incredible, and ranks as one of the best meals I’ve ever had to boot. If you need more information, I wrote an in-depth rundown of my experience at the kitchen table in January. 1723 N Halstead St, Chicago, IL 60614
9. Taco Bell Cantina
Perhaps this is just due to the draconian liquor laws in Pennsylvania and the incredible expense of getting a liquor license in Philadelphia, but the novelty of being able to get a crunchwrap and a beer was not lost on me. Maybe it’s because in addition to loving the highest of high-end food, I’m a garbage person who loves Taco Bell as well. The Baja Blast Freeze with a shot of rum was incredibly sweet, which I suppose should have been expected, but it was still a fun stop to make. And I don’t mind admitting that I would do it again. 1439 N Milwaukee Ave, Chicago, IL 60622
As you can tell, Chicago has something for everyone—and we didn’t even graze the surface. There is so much to see and do, the city requires multiple extended weeks of visiting, especially if you want to make the most of the incredible food scene. But unless you love to be cold (which I do), I would suggest avoiding visiting in the middle of January.