Three things always happen when your friends come to visit: you eat too much, you drink too much, and you spend too much money on stupid things. Being a good host and keeping everyone happy is also trickier than it should be. Having a cheap friend, a pushy friend, and a picky-eater friend all in one place can cause some serious rifts.
But don’t worry, because we know how to please everyone at the same time when it comes to food. Below is a list of fun restaurants that all serve good food at reasonable price points. So you can focus on the important things, like passive aggressively suggesting that they stay in a hotel next time.
You aren’t a good host if you don’t suggest a trip to Au Cheval. It has Chicago’s best burger (maybe the best in the entire country), and chances are whoever’s visiting has already heard of it. In case there’s a burger-hating contrarian in the group, the menu has other, almost as delicious options, like the fried chicken, or the foie gras with eggs. They don’t take reservations, and it’s always crowded, so plan to kill some time checking out the rest of the West Loop while you wait. It will be worth it to help your visitors cross this off their bucket lists.
Deep dish pizza is something Chicago is known for, and it seems to be a polarizing topic - just ask your friend from New York. So if you feel like making a case for it, go to Pequod’s. You’re here for pan-style deep dish pies, with sauce underneath the toppings (unlike traditional deep dish pizzas, which have the sauce on top). What really sets these pizzas apart is their “caramelized” crust, also known as the burnt edges of crispy cheese around the outside of a pie. There are two locations, one in Morton Grove and one in Lincoln Park, but we prefer the Lincoln Park location - it’s basically a sports bar, and perfect for a group.
Hot dogs and Italian beef sandwiches are treated almost as reverently as pizza in Chicago, and the Portillo’s in River North does both very well. So if you need something quick and classic, this is a must-stop. Just know that a trip here can be intimidating - it’s kind of a sh*tshow inside. There are tons of people in multiple lines, and the whole huge place is decorated like a garage sale (in a really clean garage). Your job is to make sure of two things: one, that everyone stays in line for Portillo’s Hot Dogs (ignore Barnelli’s, which shares the space), and two, that at least one hot dog and one Italian beef are on the table. Bonus points if you order a chocolate cake shake - that’s when you know you’ve done this spot right.
Sometimes when people from either coast visit the Midwest they expect every meal to be meat-centric and heavy. We find the best way to handle this is to meet their expectations and take them somewhere with lots of pork and beer. The Publican has both of those things, but there’s an equal amount of menu space devoted to seafood and vegetables - so you can prove there’s more to this city than the meat sweats. Plus, the space is dominated by a wooden communal table that will make everyone feel like they’re eating in a castle. So you can cross that Medieval Times trip off your to-do list.
Summer House is ideal for entertaining people who are trying to keep things on the healthier side, but the very best thing about this place is that it works for almost anyone. There are plenty of solid fish and vegetable dishes here, and an entire section of the menu is dedicated to gluten-free dishes. Plus, there’s a pastry case with excellent baked goods - most of which, thankfully, have tons of gluten.
If you’re looking to go out with a big group, 90 Miles is the spot. No other city has BYOB restaurants like Chicago, so flaunt this fact by encouraging everyone to bring their own personal handle of choice. It’s a chill atmosphere here, with colorful artwork and an open-air space. Make sure at least one person orders a cubano, and get tostones and deep fried sweet plantains for the table. Are personal handles a good idea? Of course not. But your friends will love the fact that you’re allowed to bring them.
Save Monteverde for your New York friends who like good food and won’t shut the f*ck up about how they think restaurants here probably aren’t as good. Monteverde can go toe-to-toe with the best of them, and even better, neither the prices at Monteverde nor the rent is too damn high. Order all of the pastas, particularly the cacio whey pepe, which might not sound that exciting, but we promise it is.
Trying to revert back to your college days of a quick dinner before you relax and pregame? Hit Big & Little’s. This funky, cash-only BYOB joint is meant for an easy, inexpensive, and delicious meal. Go basic with the burgers and tacos, or take things to a higher level with the soft shell crab po’ boy or french fries with foie gras. Dinner will be great even if you later realize you’re too old to have serious pregames.
Jimmy just drove in from the middle of nowhere Indiana/Michigan and wants something casual to eat immediately. Take him to Wyler Road, a sandwich shop/bar hybrid with great food and great drinks. Start with cheese curds and fried potato balls, then go for the crawfish melt or short rib sandwich. Jimmy won’t be disappointed.
Piece’s thing is New Haven-style pizza, which means a lot of red sauce, extra olive oil, and parmesan, but no mozzarella cheese. The space is huge, the pizza is great, and they brew some pretty good beer, too. It’s the epitome of a “let’s grab some pizza and beer” spot. Come here for a children’s pizza party, but with adults and alcohol, not germ-filled ball pits.
Parson’s should be an automatic choice if it’s nice out. We might not be able to eat outside year-round in Chicago, but we’ll take outdoor fried chicken part of the year over whatever birdseed concoction your friends in LA are eating on a regular basis. You may have to wait for a table, but once you get one, it’s prime real estate. Eat fried chicken and drink frozen negroni slushies for the rest of the night. In the winter, they turn the patio into an ice skating rink - just don’t eat fried chicken while you ice skate, and you’ll be good.
Topo Gigio is the wrong place for nothing and no one, and that especially includes dinner with friends in town. There’s something about the atmosphere that makes everyone purple-toothed and giggly in good company. Eat pasta, drink wine, and go where the night takes you, whether that means to the bar, or back home to reminisce about when you used to be a lot cooler.
This is a good way to do River North without spending too much money in a sceney restaurant you hate. It sounds like a diner your grandparents might hang in, but Bernie’s is actually a modern space with wood floors, bright blue booths, and an attractive open bar and kitchen. Get some of the Mediterranean small plates to share, and be sure to order a burger, too. It’s one of the best in Chicago.
Come here with a group for lots of Mexican seafood - like the Nayarit special prawns, which come with an octopus-stuffed lobster, and are cooked in a tomato-based broth with onions, garlic, and other spices. Just don’t forget to BYOB.
Show your friends you know cool things and take them to Pilsen - specifically Dusek’s, which is basically one big fun-house for eating and drinking. The restaurant inside serves great food (the iron roasted mussels and Juicy Lucy burger are must-orders), the Punch House in the basement has great drinks, and if you’re lucky, there might be a show at Thalia Hall next door, too.
A classic, old-school Italian red sauce spot. Order some pastas and split a bottle of wine or four. The portions are huge, the service is friendly, and the carpeted floors are uneven. But we wouldn’t have it any other way.
Your friends want “Chicago” pizza - but you’ve warned them deep dish is a disaster for a Friday night. Take them to Bar Siena. It’s trendy but not obnoxiously so, and all the pastas and Neapolitan pizzas are really good, so you can’t go wrong no matter what you order. Everyone will have fun and you won’t have to listen to complaints about deep dish not actually being good (it is good).
Forgot to make reservations and can’t really decide what to do? F*ck it - go to Green Street and grab some Texas BBQ in a giant party garage. After scoping out (and waiting for) a table, order your meats and sides by the pound. Then, hang out on the picnic benches as long as you please - or at least until they close (at 1am on the weekends) and kick you out.