Live in Chicago long enough and eventually you’re going to get this text: “Guess what? I’m coming into the city this weekend!”, followed by a list of demands and a request that you make all this person’s city dreams come true. Embrace the challenge by picking the perfect spot, the key to which depends upon the answer of one important question: What kind of suburbanite are they? Friends and family scared of valet parking and excited about the chance of running into Oprah? Or people who used to live in the city and made the terrible/hard/understandable decision to relocate? Either way, this guide will help you pick the right spot for your visitors.
So you met a girl at a party, and by the time you found out she actually lives in Oak Park, it was too late: you had already asked her out. Go to RPM Italian for an Italian meal that doesn’t include unlimited salad and breadsticks. It’s in River North, has a sleek and trendy vibe, and truly great food. The menu is mainly Italian small plates, pastas, and shareable mains, and the pastas are all made in house. It’s perfect if you need to go to a “hot spot” and actually have a good meal.
Nothing says “going out to dinner in Chicago” more than going to a steakhouse, and at last count there were approximately 1200 of them in River North alone. Head to RPM Steak if you’re with people cool enough to realize that Michael Jordan’s Steakhouse is as terrible as it sounds. The vibe is similar to RPM Italian (unsurprisingly, it’s from the same folks) with a trendy space, excellent food, and expensive steak. There’s a whole section of wagyu and kobe on the menu if you’re going all out, but plenty of shareable small plates and seafood you want more on the table than just meat.
This is one of Chicago’s best-known restaurants and also happens to have great food. It’s a great starter restaurant for your sister visiting from Naperville who wants to impress her friends by eating someplace adventurous, without pushing the mean girls on Facebook out of their comfort zones. The eclectic small plates menu has dishes like goat empanadas and stuff with duck tongue, but there are plenty of “safe” options too. It’s almost always booked, so you need to plan ahead if someone wants to include this in their city visit.
Your friends used to live in the city, but moved to the suburbs because they decided public schools were more important than good food. Take them to Roister. It’s from the same team as Alinea, but much more reasonably priced and easier to get into, with still excellent food. If you really want to make your friends jealous, sit in the “hearth” section and watch all the food getting made in the open kitchen. Just know you will spend the evening listening to them complain about Winnetka the entire time.
Your friend from Schaumburg wants to feel like she’s in the city. And she’s taking that literally - she straight up wants to see some views of the Chicago skyline. Cindy’s is the place for that. The menu is “new American,” you’ll find pork belly and duck breast, and while the food isn’t memorable, it’s decent. Much of it can be shared by large groups (most dishes have a “platter” option) and if you’re stuck planning a bachelorette party for your high school friend, this is a great option.
Sometimes you get someone who comes into the city seemingly against their will. They hate the traffic, the prices, and have already decided to hate wherever you take them for dinner. This is where Gibson’s comes in - it’s a typical Chicago steakhouse that also happens to have locations in the suburbs. The food is good and the portions are generous (including slices of cake that are literally six pounds) and the familiarity should placate anyone who’s mad about paying $42 for parking.
You know your friend from your first job right out of college? The one you used to day drink with before they started working out in Arlington Heights? Well, they’re back for the weekend, and want to recapture those days when you’d wake up and need to search through the mail to find out where you slept last night. Tacos and drinks on the huge patio at Big Star in Wicker Park is the move. The tacos are decent, with the al pastor being the best, and the drink menu has lots of whiskey and mezcal. It’s always loud and crowded, and perfect for pretending that there is no one waiting for you back at the subdivision.
Summer House is ideal for the girl you did a summer internship with, who now works at Kraft in the burbs, where she wishes there were a SoulCycle nearby. Summer House has a menu that has plenty of options for people who are trying to keep things on the healthier side. There are a lot of solid seafood and vegetable dishes, along with an entire section dedicated for gluten free. The space is airy and full of light, and makes you feel healthy even if you would rather just order from their pastry case.
Bar Siena is where you take the friend who got drunk and would fall into the bonfire at parties. The space is loud and trendy, with a huge bar dominating the first floor and a larger dining area upstairs that’s perfect for groups. Pastas and wood-fired pizzas make up most of the menu, and many of them are really great. The prosciutto and fig pizza has a great balance of sweet and savory, and the gnocchi is pillowy and delicious. It’s a great spot to get a little crazy, and since it’s not in River North, you won’t risk losing them in a sea of other drunken suburbanites.
We never got the Hot Doug mania, but if your friend is one of those people who moved before they closed and still can’t get over it, take them G Dog. It’s run by former Hot Doug employees and they have many of the same gourmet hot dogs (like one with alligator sausage) a really great classic Chicago Dog, and the same duck fat fries. If you have a nostalgic friend in town whose most creative idea is to get a hot dog, this is a good place to do it.