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, pushy friend, and picky-eater friend all in one place can cause serious rifts.
But don't fret, 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. These are the restaurants to take your out-of-town friends to eat.
If you want a way for the whole crew to go out together, 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. The vibes here are very Cuban with a relaxed atmosphere, colorful artwork, and open-air space. Are personal handles a good idea? Of course not. But your friends will love the fact you're allowed to do it.
Save Monteverde for your New York friends who like good food and won't shut the f*ck up about the fact they think restaurants here probably aren't as good. Monteverde can go toe-to-toe with the best of 'em, and even better, neither the prices at Monteverde nor the rent is too damn high. Order all of the pastas, particularly the squash tortoloni, 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. The funky, cash-only BYOB joint is meant for an easy, cheap, and delicious meal. Go basic with the burgers and tacos, or step things up a notch 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 pre-games.
Jimmy just drove in from the middle of nowhere Indiana/Michigan and wants something casual to eat immediately. Take him to Wyler Road to post up at the bar. Wyler Road is a sandwhich shop-bar hybrid with both great food and drinks. Start with cheese curds and fried potato balls, and get a little weird with the veal heart philly or keep it familiar with a short rib sandwich. Jimmy will feel right at home.
Piece is basically a children's pizza party with booze. Their thing is New Haven style pizza, which means a lot of red sauce, extra olive, and parmesan, but no mozzarella cheese. It's the epitome of let's grab some pizza and beer.
Parson's should be an automatic if it's nice out. We might not be able to eat outside year-round, but we'll take outdoor fried chicken part of the year over whatever disgusting birdseed concoction your friends in L.A. eat on a regular basis. Make it a Saturday afternoon or early evening trip because you're going to have to wait for a table. But once you get one, oh man is it prime real estate. Eat fried chicken and drink frozen negroni slushies the rest of the night.
This is a good way to get a bit of the posh sense of River North without spending too much money in the presence of pretentious people you hate. Despite sounding like a diner your grandparents would hang, Bernie’s is a modern space with wood floors, bright blue booths, and an open bar and kitchen that make everything look cool.
Topo Gigio is the wrong place for 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
If your crew is the adventurous type, then Veneno is a guaranteed good time. It’s a dive BYOB Mexican seafood restaurant that specializes in Nayarit style food. Come here for the Nayarit special prawns, which come cooked in a thin tomato-based broth with onions, garlic,and others spices, plus a lobster stuffed with an octopus mix.
Show your friends you know cool things and take them to Pilsen. Dusek's is basically one big fun-house of different rooms all in one place. The restaurant itself serves great food, Punch House in the basement has great drinks, and Tack Room, the piano bar next door, is also a fun a time.
Becky lives in the East Village and so far has complained all of the restaurants in Chicago are uncomfortably large. Make Becky feel right at home in the safety of Bar Marta. It's best reserved for a small dinner crew (six at most), and the small, dark space feels very hip. Order both the cacio pepe and meatballs, then work the rest of your meal around them.
Longman & Eagle looks like the kind of place 50 Brawny Paper Towel guys should be sitting at the bar pounding whisky after a long day of chopping wood. Good news is the whisky list and food match the vibe. Try all of the whisky and eat meat-centric dishes prepared in an elevated way. The whole situation is very Midwest.
Old school Italian red sauce joint at its finest. Go for the pastas, D-List celebrity pictures on the wall, and split a bottle of wine or four.
Your friends want "Chicago" pizza, but you try to warn them deep-dish is a disaster for a Friday night. Be a smart host and take them to the trendy Bar Siena instead. The play here is pizza and pasta to share. Everyone will have fun and you won't have to listen to complaints about deep-dish not actually being good (it is good).
If it's 70+ and sunny ignore everything we just said about Bar Siena and apply it to Parlor Pizza instead. Summer is precious here and no city takes advantage of it better. Put that fact on display.
Forget to make reservations and can't really decide what to do? F*ck it - go to Green Street and grab cafeteria Texas style BBQ in a giant party garage. You can sit and hang at the picnic benches as long as you please, or at least until they close 1am on the weekends and kick you out.