Clients are like plants - except instead of watering them and placing them in direct sunlight, you need to take them to dinner sometimes. But you can’t just take them to any restaurant. You need someplace that’s nice but not awkwardly formal, and trendy while still being quiet enough for a conversation. It should also have food options that will appeal to just about everyone. Here are 12 corporate-card-worthy spots that meet all these criteria.
Going to Chicago Cut is like taking a field trip to a corporate zoo. Mainly because this steakhouse is at the bottom of an office building, and full of successful-looking people in power suits who may or may not be selling Senate seats. But the food is excellent, the space has an impressive view of the Chicago River, and you don’t need a permission slip to eat here. Except maybe from the accounting department.
Because Chicago is known for steakhouses, there’s a 99% chance that an out-of-town client will want to go to one. And thanks to its great food and The League, Gibsons is the most iconic and well-known. It’s perfect for experiencing all the things people love about this city - not only does it have fantastic steaks and sides, but it also has a relaxed atmosphere that will lull clients into a sense of security. They are having dinner with a nice Midwesterner (you), after all.
This is the Italian counterpart to Gibson’s Steakhouse, and it looks and feels more expensive. It has giant leather booths, plus floor to ceiling windows with a fantastic view. Don’t let the “Italia” in the name prevent you from ordering a steak - this place has the same delicious steaks you’ll find at the original, and they’re actually better than the Italian dishes on the menu. The space is huge and has multiple levels, so after dinner, head to the third floor bar where you can sit around a fireplace and discuss important topics like Q4 projections and what to order for second dessert.
RPM Italian has everything you want in a big, sceney River North restaurant. It’s modern and trendy without being obnoxious, and it has fantastic pastas (like the bucatini), along with attentive service. Even though it is an Italian restaurant, it has plenty of non-pasta things on the menu, too - so if you find out on the ride over that your client is keto and gluten-free, you won’t need to worry.
Since Chicago likes making Italian/steak companion restaurants, this is the steakhouse version of RPM Italian. But it’s a little bigger, and has two levels. So you can eat in the main dining room, or you can eat in the upstairs room overlooking the first floor of the restaurant. Wherever you sit, your client has a pretty good chance of using silverware previously touched by Justin Bieber or a Chicago Bear.
You might have noticed a pattern: there are a lot of steakhouses on this guide. But while Bavette’s is technically a steakhouse, we don’t treat it like one. The best things on the menu here aren’t steak, so go for the fantastic seafood towers, the mushroom stroganoff, and the pork chop. Plus, the dark speakeasy atmosphere with 1920s jazz music makes Bavette’s stand out from most of the spots in River North. (Speaking of darkness, take the opportunity to educate your clients about one of Chicago’s proudest restaurant traditions.)
If social media, Google, and LinkedIn have given you zero useful information about your clients’ eating habits, Somerset is still a good bet. This Gold Coast spot has a well-rounded menu that will work for just about anyone, and also happens to be one of the best restaurants in the whole city. You can order anything from beet tartare to a piece of fish to roasted chicken or a cheeseburger - and although this place is located in a neighborhood full of dogs in baby carriages, the atmosphere is actually low-key.
Don’t let conservative-looking suits and reasonable shoes fool you. Sometimes a client wants to party. When that’s the case, go to Aba in the West Loop. This place is a scene, but it’s a scene that comes with fantastic food. It’s always crowded, but the space is beautiful, and there’s a huge rooftop patio that’s perfect for hanging out over drinks. Most things on the Mediterranean menu are meant to be shared, so pay attention to your client’s share-plate habits - it might give you valuable insight for future negotiations.
Pacific Standard Time is a large, busy restaurant that’s vaguely California-themed. So if you’re entertaining someone from LA, they might be interested to know that Chicago’s version of the West Coast serves pizza with a side of ranch dressing. That being said, the rest of the menu has a lot of seasonal vegetable dishes, and overall the food is interesting and tasty. Plus, the space is massive, so if your dinner goes downhill, you can escape into the crowd.
Monteverde serves some of the best Italian food in the city, and dinner here is guaranteed to make everyone at the table happy. Every pasta dish here is fantastic - in particular the cacio e pepe, which is a menu staple. But the non-pasta (like the stuffed cabbage appetizer or the pork shank) is great, too, and what makes this place even better is that it’s not too expensive. Not that you’re paying for this meal, anyway. Just make sure to plan ahead - it’s hard to get a reservation.
This Argentinian spot is a good place go with the type of client who might get slightly drunk and/or talk about confidential information at a volume that makes you nervous. It’s a little loud, and the open kitchen and live fire grill will keep everyone distracted from your trade secrets. Everything that grill touches is worth ordering - from the steak and pork to the grilled oysters and vegetables.
Taking a client to Alinea is like showing up for a first date in a wedding dress. In other words, it’s coming on way too strong. Roister is from the same team as Alinea, but it’s more casual, and way less intense. The busy open kitchen in the middle of the dining room keeps the atmosphere fun and interesting, and the food is still fantastic. Make sure to order the fried chicken, and the foie gras candy bar for dessert. Because like with children, there’s no shame in bribing your clients with candy.