Chicago has a surprising amount of restaurants built around fancy tasting menus. Even people in other cities like New York or L.A., where you would expect to find these kinds of restaurants, are surprised to find how many exist here. Is it normal to spend a couple hundred dollars per person on dinner? Nope. But it can be a lot of fun, so you better know what you’re getting into before blindly committing to such an expensive meal.
Figuring out which one of these places is right for your particular situation can be difficult, which is why we want to help. Some spots are super fancy and sophisticated, while others encourage you to get drunk and have fun. That’s why we’ve broken things down into Beginner, Intermediate, Advanced, and Expert categories, just to give you a sense of what to expect. Of course, you can always dive right into any of these places and still have a great time.
Roister is the most casual restaurant from the Alinea Group, and a good intro session to tasting menus. As far as cost and fanciness on the tasting menu scale, it’s like being the dumbest kid at Harvard Law - not outrageous but still kind of a big deal. If you don’t think you’re ready for a full-blown experience, this is a great way to get your feet wet for $85. The food is more approachable in a casual and fun setting, but it’s still incredible, which makes it the perfect way to get in the mix.
Food: $85-$95 (plus tax & 20% service charge)
All drinks a la carte
North Pond is named after the pond in Lincoln Park directly next to the zoo, which is exactly where this restaurant is. It’s a beautiful setting where you can stare out over the park, making it great for things like anniversary dinners or inspiration to write the next coming of Walden. It’s a quiet and reserved place, which also means the crowd skews a little older. But there’s nothing wrong with that, and there’s nothing wrong with a reasonably priced tasting menu either.
Food: $95 (plus tax & service charge)
Optional Wine Paring: $45
Schwa is one of a kind. Yes, it’s an expensive tasting menu situation, but it’s also a damn party. The music blasts loudly and will casually switch from classic rock to rap, and not only can you drink a lot (there’s a BYOB policy) - you’re encouraged to. Besides, there’s a 100% chance the staff will end up f*cked up too. It’s an awesome ambience, but the food is also refined and high-class in the most interesting and playful kind of way: we’ve been given homemade air fresheners to sniff that altered our sense of taste while drinking bourbon, eaten elk sniped from a helicopter (their words), and had dessert meant to simulate peeing in the snow on a cold day. It’s like having your drunk stoner friends screwing around in the kitchen, but those friends happen to be some of the very best chefs around. Schwa is a truly wild and fun place.
Food: ~$150 (plus tax & service charge)
El Ideas wants to make fine dining fun, and they succeed in accomplishing that goal. It’s not as wild a place as Schwa, but it’s also BYOB and more approachable. At least it’s more approachable once you find it, because you’d never notice it on a random stretch of 14th Street near Western unless you’re specifically on the hunt. The kitchen encourages you to kick it with them as they basically talk you through what they’re doing, which can be really helpful and fun if you don’t normally do this kind of thing. But it’s also fun for the expert who wants to know more about the process of creating such an exciting meal.
Food: $155 or $175 for front row seats (plus tax & service charge)
The chef and owner of Goosefoot spent a number of years as the man in charge of the kitchen at the upscale Les Nomades (see below) before he decided to go out on his own. A good way to think of Goosefoot is that the owner took the core values of everything he was doing at Les Nomades and freed himself from the stuffiness there. Like a peacock, he let himself fly. So while Goosefoot is still very elegant and sophisticated, there’s a bit of casual Ravenswood style, and more fun to be had here all around. The BYOB policy definitely helps.
Food: $220 (includes tax & 20% service charge)
Elizabeth is a small restaurant in Lincoln Square that feels a little like grandma’s house when you first walk in. It’s perfectly homey and a comfortable place to hang, which is how you’ll feel throughout the entire meal. It’s also run by the same woman behind one of our favorite places ever, the short-lived Bunny The Micro Bakery. The food is usually very plant focused, but they’re doing amazing things with simple ingredients. Is that the best homemade bread you’ve ever eaten? Yes. Should you start foraging your own mushrooms? You could, but you might poison yourself. Is that a foie gras owl sprinkled in edible flowers? Oh ya, and it’s delicious. If you’re not a big meat eater, Elizabeth is definitely the spot for you. And even if you love a good steakhouse, Elizabeth will push you to appreciate plants and other ingredients more than you knew you could.
Food: Varies depending on menu, ~$150 (plus tax & 20% service charge)
Optional Wine Pairing: ~$100
Optional Beer Pairing: ~$65
Acadia flies under the radar a bit, and we attribute that to its South Loop location. If this place was in the West Loop it would inevitably get a lot more love. But it’s one of the better-kept secrets in town, serving contemporary American food in a sleek setting. And the combination of approachable food and ingredients with perfect service and attention to detail is what might make Acadia the right place for you. The food is influenced by New England, which means you won’t be scared off by weird ingredients and French names you can’t pronounce, if those are things you worry about. Find comfort in the fact you’ll be familiar with everything that hits your plate.
Food - 5 course tasting menu: $100-$115 + $85 optional wine pairing (plus tax & 23% service charge)
Food - 10 course tasting menu: $150-$185 + $125 optional wine pairing (plus tax & 23% service charge)
Smyth wants you to think you’re dining in someone’s living room. On one hand, there isn’t a giant bowl of peanut M&M’s or chips sitting out on the table, which is pretty much required if you want us to come hang at your place. But on the other, Smyth’s overall setup feels like you’re in a well-appointed living room, especially because a husband and wife duo run the place. This is still a relatively new spot, so it’s settling into a specific role and finding its way, but both the food and ambience are a tribute to Smyth County, Virginia. So, just like Acadia, this place focuses on flavors and dishes you’ll recognize. The brick walls and loft vibes in this Ada St. location in the West Loop also help - the aesthetic is a big part of the overall appeal.
Food - 8 courses: $135 (plus tax & 20% service charge)
Food - 12 courses: $195 (plus tax & 20% service charge)
Optional Beverage Pairing: $85
Ask a cab driver to take you to Oriole and they’ll think you’re up to something sketchy in a weird alleyway near the highway and Fulton Market. But hiding on the one random block of Walnut St. is Oriole, a cozy 28 seat restaurant that blends right into its surroundings. There’s no shtick at Oriole or focus on one particular cuisine - one second you’ll have some nigiri and yuzu, and the next there’s Alaskan king crab or thinly sliced Spanish ham in the mix. The fact that you don’t know what’s coming next is a lot of fun, and they do it in an intimate environment that still manages to be friendly, inviting, and not stuffy at all.
Food: $175 (plus tax & 20% service charge)
Optional Wine Pairing: $125
Optional Mixed Beer, Sake, Wine Pairing: $75
Les Nomades opened in 1978 as a private club, and even though the Streeterville Brownstone building became open to the public in the ’90s, it still maintains the same sense of exclusivity. We’re not saying that’s a bad thing, but it’s definitely something to keep in mind. This an old-school, French-feeling experience in terms of the ambience, food, and decor. If you have wealthy Gilmore Girls type grandparents, this would be a great place to have them take you. But if you’re younger and looking to experiment with fine dining for the first time, we’d probably steer you elsewhere.
Food $130 4-course prix fixe or $145 5-course prix fixe (plus tax & service charge)
You can find excellent restaurants in this city in places you would least expect, like the top floor of the Chicago Stock Exchange in the Loop. This 40th-floor restaurant can be summed up by three particular traits: fancy French food, great French wines, and excellent views of the city from the south end of the Loop. Everything about Everest screams sophisticated in a French stockbroker kind of way, except people here are nice to you.
Food: $168 (plus tax & service charge)
Optional Wine Pairing: $98
The beauty of Next is that the menu changes a few different times a year, and the menu heavily dictates what to expect from both the ambience and style of the place as a whole. Past menus have ranged from Vegan to Modern Chinese to Chicago Steakhouse to “Childhood” to even a tribute to The French Laundry. Each version will be different, but you can always count on an interactive experience with the staff and kitchen. If there’s a particular theme and menu that catches your eye, we encourage you to go for it.
Food: Varies depending on menu. Expect~$200+ (plus tax & 20% service charge)
Optional Wine Pairing: Varies depending menu. Expect ~$200
Are you comfortable spending around $500+ on dinner for one person? It sounds like an absolutely absurd question for a majority of people out there. But Alinea isn’t a normal dinner. It’s a pageant show and science project all rolled up into one, and they just so happen to feed you in the process. Here’s our cautionary remark - you have to appreciate these sorts of theatrics and be willing to ignore how expensive it is. But there’s a reason Alinea is regarded as one of the best restaurants in the entire world. Part of the fun is in surprises, but you can expect everything from balloons made of apples that make you giggle as you suck helium out of them, to your table becoming a canvas for food art. It’s a one-of-a-kind experience and absolutely worth going if you can find a way to swing it.
Food: $175-$385 (plus tax & 20% service charge)
Optional Wine Pairings: $115-$315