Chicago has a lot going for it. We don’t live along an active fault line, we have plenty of alleys perfect for hiding our garbage and rats, and the cost of living in the city is reasonable. That being said, we’re still in flyover country.
But occasionally airplanes do stop here, dropping off people from the East and West Coasts (among other places). When the people in question are friends of yours, you need to know where to take them. Keep in mind that Midwestern food, much like zero gravity, is something a person should be eased into - so here are some places where your visitors might feel at home, in addition to a few where they’ll definitely know they’ve made it to Chicago.
Impressing New Yorkers with an Italian restaurant is hard. But you can take them to Monteverde in the West Loop with confidence. Every pasta dish here is fantastic - in particular the cacio e pepe, which is a menu staple. But the non-pasta is great, too (try the stuffed cabbage appetizer or the pork shank). It’s the kind of place that might make someone (briefly) stop talking about their favorite spot in the West Village.
Giant in Logan Square makes classic Midwestern dishes like broccoli and cheese into must-orders, and turns crab salad into a clever excuse for eating waffle fries. In other words, it elevates everything fried and cheesy. The less-fried items (for example, the pastas) are also great, and overall, we have yet to find something we don’t like. The casual space has lots of upbeat energy, and the back patio is perfect for a small group during the summer.
Au Cheval has the best burger in the city (maybe even the world). This makes it a must-stop for people visiting Chicago, no matter where they’re from. Just plan on a wait, but assure everyone that it’s worth it. Especially that friend from New York who had the inspired-by-Au Cheval burger at 4 Charles Prime Rib six months ago. There’s nothing like the original.
It’s required by law that you take all visitors to Chicago out for deep dish pizza. And when you have a skeptic on your hands, it’s essential that you pick the right place. There are lots of spots to choose from, but Pequod’s is the best. The pizza here is pan-style (so it doesn’t have the river of cheese you get from a classic deep dish pie), and the best part is the caramelized crust. Bring tissues for when the tears of joy inevitably roll down your friends’ cheeks.
Occasionally you do need to give someone the opportunity to capsize in a river of cheese. Chicago Pizza And Oven Grinder is the place to do this. Go there and order the pizza pot pie. Fair warning, this thing is ugly - it’s a bowl-shaped crust filled with sauce and toppings, not to mention an intimidating amount of cheese. But it’s delicious, and in a category by itself. Plus, this place is in the basement level of a three-story brick building, and feels like a Prohibition-era hideout (if the Prohibition had prohibited cheese).
Au Cheval doesn’t serve the only destination-worthy burger in this city. We also have The Region, a small counter-service place in Roscoe Village. On first glance, these burgers are unsightly - the patty goes way past the edges of the bun, and seems monstrous. But that’s only because the meat has been flattened on a grill, creating delicious lacy caramelized edges. Include a Black Cow Milkshake (a root beer float with chocolate syrup) in your order, along with some onion rings. Not a bad candidate for helping someone finally let go of an obsession with In-N-Out and/or Shake Shack (although realistically, good luck with that).
Your colleague from LA is in town, and you’re in the market for a kind of healthy breakfast. Go to Left Coast. This place has the type of food that someone who visits the ocean every day - or at least lives in a place where that would theoretically be possible - might eat. Come for tofu-filled breakfast burritos, avocado toast topped with orange slices, and acai bowls. At the Lakeview location, you can even sit outside. Just tell your coworker to imagine that the taxis are rollerbladers.
One of the best parts of eating farm-to-table food in the Midwest is that we really are surrounded by farms. And Daisies in Logan Square is the kind of place where your server will let you know not only where your lettuce came from, but also what kind of mood it was in when it arrived that morning. The menu here is pasta-focused, but there are also appetizers like cheese curds. Those are a must-order - because you can’t let anyone from the coast leave without eating some deep-fried cheese.
Your cousin who moved to California a few years ago has returned. The first thing she did when she landed was eat a hot dog at O’Hare, but now she wants something quinoa-adjacent for lunch. Put West Coast-inspired Summer House Santa Monica on the itinerary. There’s a big skylight in the dining room, and a healthy menu with salads, grilled fish tacos, and plenty of avocados. She can always grab a cookie from the pastry case on the way out, once the hot dog high has worn off.
Siena Tavern in River North is the best version of a sceney Chicago restaurant. Meaning this place is huge, with pounding music and gigantic booths. Plus, it has great food, including housemade pastas and a Chicago-sized (i.e. very big) wagyu meatball appetizer. It’s the perfect spot for someone who frequents small neighborhood spots in Manhattan - they’ll feel like they’re in Honey I Shrunk The Kids, and you’ll be entertained by watching them avoid knocking over wine glasses with the surfboard-sized menus.
We don’t blame our out-of-town friends for not being excited about the prospect of eating sushi in the Midwest. Lake Michigan isn’t fooling anyone - it’s not an ocean, and it hasn’t produced any sushi-grade fish recently. But Raisu, a casual sushi place in Albany Park, will make you forget about that. The food here is very good, the prices are reasonable (you can set a budget for omakase starting at $50), and the friendly service rounds out the whole enjoyable experience.
There’s a good chance that the person visiting you has heard of Alinea and Next, but those restaurants are expensive and take a lot of planning to get into. Go to Roister, owned by the same team, instead. You’ll find similarly interesting food in a much more accessible (and affordable) setting. Order the fried potatoes topped with bonito flakes and served with tofu mayonnaise, and get a foie gras candy bar for everyone at the table. Try to sit by the hearth, where you can watch them cook on the live fire.
At some point, a visitor to Chicago might get overwhelmed by our heavy food and want a detox - a steady diet of hot dogs and deep dish pizza can inspire this type of thing, or so we’ve heard. Take care of this with a meal at Ema. The Mediterranean small plates are light and fresh, and the dining room has enough plants and sunshine to make your friends feel like they’re at home, where there isn’t quite so much cheese.
Go to Gibsons in the Gold Coast for a classic Chicago steakhouse experience. The interior looks like it hasn’t changed in decades, and the servers will bring the different types of meat (and occasionally lobster) you can choose from on a platter, to be selected tableside. The steaks are always perfectly seasoned and cooked. Make sure you order a six-pound (literally) piece of cake for dessert. This place couldn’t be any more Chicago if it wore a Bears sweatshirt.
This casual spot in Pilsen makes the list for two reasons. One, it’s an excellent Mexican restaurant - you can’t go wrong with anything on the long menu. Two, it’s BYOB. This is something many of us in Chicago take for granted (we have a lot of BYOB options), but it will probably make your friends from less-BYOB-happy cities jealous.
You’re not going to this old-fashioned ice cream parlor for a tiny scoop of cardamom-scented ice cream topped with free-range honeysuckle tendrils. You’re at Margie’s for giant sundaes served in clamshell bowls with gravy boats of homemade hot fudge and caramel on the side. This place has been around since 1921, and the interior looks like your grandparents’ garage sale. There’s a jukebox, old-timey photographs, and stuffed animals that look like they were won at a carnival 30 years ago. If you’ve ever wanted to eat one of those cartoon-style sundaes with 15 scoops of ice cream, you can do it here (it’s called the World’s Largest Terrapin). Good luck fitting your friends on the plane.