There are people who visit you who you wish lived here permanently, whether it’s because they’re your soulmate or simply someone you trust to house-sit for you. It’s true that Chicago has Westeros-caliber winters and an abundance of red light cameras, but living here also means affordable rent, bountiful opportunities to see Hamilton, and a never-ending supply of restaurants to try. These 19 spots will help convince even the most skeptical soulmate/dog walker to break their lease to move here.
Discussing the possibility of a life in Chicago often means encountering a person’s deep, long-held prejudices around pizza. It’s a common misconception that Chicago only focuses on deep dish, and you can disprove this with a trip to Bebu. The excellent pizza at this Lincoln Park spot has a thin, perfectly chewy and bubbled crust, along with delicious toppings. There’s a mixture of creative pies (the littleneck clam is a standout) and classics like a sopressata and Calabrian chili honey. Luckily you can order pizzas half and half, which helps showcase our city’s pizza diversity.
After you’ve proven we have more than deep dish, it’s time to take them to eat deep dish. Because it might not be our choice for everyday delivery, but it’s delicious. Go to Pequod’s, whose pizza is the most compelling case for moving here. The pies have the perfect amount of cheese and spicy tomato sauce, with a fantastic caramelized crust of crispy cheese around the edges that makes winter more bearable by helping you hibernate through it. Just avoid bringing up the Polar Vortex until after they sign their lease.
Au Cheval is basically Chicago’s Venus flytrap. It has the best burger in the city, and it’s such a popular destination there’s a case for creating a shuttle that goes straight from O’Hare to here. Once someone tries this burger, they’ll have a hard time imagining a life without regular access to it. That’s when you can go in for the kill: reveal that there are several versions of the same team’s Au Cheval burger throughout the city, like at Small Cheval and Gilt Bar, where people can get fixes without the long wait.
You can criticize our weather and our corrupt politicians, but you can’t criticize Chicago’s incredible Mexican food, and 5 Rabanitos in Pilsen is the best way to show it off. It’s a BYOB spot with a long menu of delicious and affordable options. There’s no wrong way to order here - get the tacos, anything from the huge vegetarian menu, the carne asada, and the very spicy ahogada torta.
Yes, Kyoten in Logan Square is very expensive (a $220 20-course omakase), so it probably won’t be making it into any transplant’s weekly rotation. But the sushi here is the best in the city, and it can make anyone forget that we’re not near any oceans. The menu involves a lot of delicious nigiri (made with heavily seasoned large-grain rice) and a number of creative small plates, like rendered beef fat poured over rice, or fried tilefish with caviar and creme fraiche. It will impress your friend enough that you will soon be able to rely on them to water your plants while you’re on vacation.
Avec started doing small plates and communal dining before most other restaurants decided that individual entrees and privacy were a thing of the past. And because the food here is consistently good, it’s one of the only restaurants where you won’t be irritated getting bumped every time a fellow diner gets up to go to the bathroom. Order the taleggio flatbread (add honey) and the chorizo-stuffed bacon-wrapped dates. Placate your visitor with this delicious food while you evade their questions about rent prices in the West Loop.
Parachute has been around since 2014, which makes it practically a classic establishment by Chicago restaurant standards and might make it feel like old news. But this place is still incredibly popular and busy, and every time we come here we’re reminded why. The Korean/American food here is always impressive. You can expect dishes like ddukbokki with pork sofrito, perfectly fried japchae tempura, and a seafood bibimbap that sounds simple but tastes anything but. Parachute also has the kind of service that shows why Midwesterners have a reputation for being very nice, proving that even Chicago’s busiest spots can make you feel welcome.
Chicago is known for pizza, steaks, burgers, and having the largest naturally occurring population of Top Chef contestants in the wild. So throw your friend a curveball with a spot like Dancen in Lincoln Square. It’s a small, dark spot with tasty Korean bar food and more black lights than a Spencer’s Gifts in 1996. Come here and order the fire chicken: chunks of marinated chicken are grilled on an open flame behind the bar until the marinade becomes charred and caramelized. Delicious and incredibly spicy, it comes with a Thousand Island-dressed cabbage slaw to balance out the heat.
Big cities are generally expensive, and if your visitor buys gum at CVS and discovers Chicago’s 78% sales tax, they’ll be concerned. Luckily we have Athenian Room to soothe them. It’s an extremely casual Greek spot in Lincoln Park with huge, reasonably priced portions. The must-order dish (and reason we send everyone here) is the kalamata chicken, roasted and served with fantastic chicken-jus-soaked fries we’d happily eat every day of the year.
Soule is a restaurant that has the Feel Good Factor™. This means it’s capable of putting somebody in a positive mood even if they spent their first two hours in Chicago stuck on the tarmac at O’Hare. The upbeat atmosphere and delicious soul food (like shrimp and grits, fried green tomatoes, and peach cobbler) will work like culinary Xanax on any out-of-towner.
Yes, winter here is horrible, and there’s no way to sugarcoat it. So a good strategy to get your sister to move here is scheduling her visit during the summer, when you can take her to Parson’s for fried chicken, negroni slushies, and outdoor ping pong. It’s one of Chicago’s Outdoor Greatest Hits and highlights that we have nice large patios where people don’t have to be stacked like firewood. This city has some space, people.
Our city has a lot of steakhouses. We bet if you look outside you’ll either see one, the future home of one, or a person suddenly having the idea to open one. If you need to convince your carnivore brother from Dallas to move here, take him to Gibsons in the Gold Coast. It’s a local classic with everything you want in a Chicago steakhouse: large portions of perfectly cooked meat, giant baked potatoes, and six-pound desserts.
This little spot on the Southport Corridor of Lakeview serves breakfast seven days a week and has one of Chicago’s best brunches - which the two of you will need after spending the night dancing at Slippery Slope. You’ll find delicious bread pudding pancakes with vanilla anglaise and some fantastic breakfast sandwiches on housemade English muffins. Since it’s popular there will probably be a wait, but you can use the opportunity to walk around the family-friendly neighborhood and show off the city’s unusual amount of trees.
Your friend lives three hours from Manhattan but still won’t shut up about New York’s great Italian restaurants. Take her to Monteverde. Every dish here is fantastic, from the housemade cacio e pepe and tortelli di zucca, to the ragu alla Napoletana (with perfectly cooked pork shank, sausage, meatballs, and fusilli), which is one of the most delicious plates of food we’ve ever eaten.
Technically Portillo’s is a chain that exists in six other states. But it started here in Chicago, and there’s a good chance your cousin (and hopefully future on-call babysitter) doesn’t have access to this delicious Italian beef where they live, not to mention the Portillo’s chocolate cake. Take them to the one in River North with a drive-thru and use the wait time to demonstrate how to secure the car seat.
This is the kind of restaurant that shows off how even Chicago’s casual-enough-for-a-Tuesday neighborhood spots are fantastic. On the surface, Giant’s menu looks like every other New American menu you might have encountered over the past decade: small plates full of meat, seafood, and vegetables. But this place somehow manages to make a dish like broccoli and cheese a must-order. (You also need the crab salad with homemade waffle fries, and a pasta like tagliatelle with crab and uni butter.)
Your best friend from college is living in Brooklyn, renting a 250-square-foot apartment, and trying to do the opposite of everything she’s seen on Girls. But she can’t let go of the whole New York-style pizza thing. Let her know she won’t have to abandon it completely by bringing her to Jimmy’s in Lincoln Square. This place has giant foldable slices, including a white pie made with ricotta, and their pepperoni forms perfectly greasy little cups. A trip here will help her transition to her soon to be new habitat.
If your long-distance boyfriend in Newark currently does most of his grocery shopping at a 7-Eleven, take him to Daisies the next time he’s in town. This charming restaurant in Logan Square uses seasonal local ingredients, and it’s the kind of place where the servers will tell you all about the produce you’re about to eat - the farm it came from, the truck it traveled on, and the CVV code on the back of its debit card. Order one of the housemade pastas, like the beet agnolotti or tajarin topped with cracklins. Then watch his life change as he eats something that wasn’t created in a laboratory.
Unlike other big cities (LA, for example), Chicago’s sceney restaurants can actually be really good. Take RPM Italian, a quintessential River North restaurant owned by E! reality stars. It has trendy music, big booths that can fit eight of your closest friends, and an interior so large it’s amazing it fits on a single city block. Most importantly, though, the Italian food is delicious. It’s a downtown Chicago restaurant at its best: over-the-top, a little ridiculous, and very enjoyable. If someone doesn’t like this place, they probably shouldn’t move here anyway.