Special occasions remind us of the famous saying about obscenity: You know it when you see it. Sometimes it’s obvious - maybe you’re getting engaged or celebrating a major birthday - and sometimes you just want to go big on a particularly awesome Tuesday. It doesn’t matter why you’re celebrating, but if that’s what you’re doing, you’re going to want to go someplace exciting. Someplace that probably requires advance planning, costs more than you’d usually spend, and has extra-good food and service. These are the best places in Chicago for a special occasion, no matter what it is. This list really runs the gamut from Alinea, where you might go once in your life, to the kind of places where you’d go to celebrate getting your security deposit back.
This is one of the most famous restaurants in the world, and choosing to have a meal here is pretty much a mic drop. Alinea has three Michelin stars, and its tasting menus can cost anywhere between $300 and $500 per person. Your meal won’t just be expensive - it’s also guaranteed to be bonkers. It’s molecular gastronomy-palooza here, with lots of theatrics (like edible balloons), and dinner will be a one-of-a-kind - maybe even a once-in-a-lifetime - experience. You can always use those savings bonds grandma gave you if you decide to go again.
Grace is the other Chicago restaurant with three Michelin stars, and here you’ll get to choose between two tasting menus: “Flora” and “Fauna,” each $235 per person. There are plenty of molecular gastronomy touches here as well, but it’s a little less Bill Nye than Alinea. It’s still a heavy hitter for a special occasion, and the food won’t be so distracting that you can’t actually talk to the people at your table.
Naha in River North is often overlooked, but it’s an excellent option if you want a classic fancy dining experience. The food is Mediterranean, and it’s a pretty standard appetizer/entree/dessert situation, so you won’t get a lecture on how many small plates you should share. It’s probably the right choice if you’re looking to celebrate your grandparents’ anniversary (unless your grandparents happen to be molecular gastronomists).
This is an upscale French place in River North, and it has the same traditional entree/appetizer/dessert-style menu as Naha, its sister restaurant. The food at Brindille is outstanding, but this is an especially good choice if you get nerdy over extra touches. For example, your server may casually inform you that the silverware you’ve been using is 100 years old.
We like this Lincoln Park spot for all sorts of special occasions. It feels fancy, but not in an old-school way - the best way we can describe it is to say that you kind of feel like you’re eating in Labyrinth. The food is modern American, and plated very prettily. Even something as awful-sounding as turnip soup is memorable here.
If you want to feel like you’ve secured tickets for the last rocket ship leaving Earth, consider making a reservation at Next. This place is owned by the Alinea folks, but unlike Alinea, Next has three different themed tasting meals every year (e.g. Ancient Rome, Hollywood, and Paris 1906). Tickets tend to sell out as soon as they’re released. You’ll experience molecular theatrics similar to those at Alinea, but not as many, and a meal here starts at around $200.
Roister serves outstanding food from the same team that runs Alinea and Next, but you order a la carte, and prices are far more reasonable (though it’s still not cheap). The food is varied and interesting: fried potatoes are topped with bonito flakes, and the whole chicken platter has some of the best fried chicken in the city. You still need to buy a ticket in advance, but at least getting your hands on one won’t require scalpers or taking a day off work.
Publican and Avec are two of our favorite restaurants, but it’s easy to forget about the O.G. fine dining spot from the same restaurant group that preceded them both. Blackbird does beautifully plated American food in a minimalist environment, a complete departure from the heaping platters of pork at Publican, and the crazy-crowded space at Avec.
This is a very old-school steakhouse, and you should find at least one occasion to have a meal here. Your server will have a jacket, your table will have a tablecloth, and you’ll get a basket of bread at the beginning of your meal. The menu is standard steak and seafood, and all of it is delicious.
This is technically a steakhouse, but we think of GT Prime more as a meat-centric shareable plates restaurant that happens to have steak. It’s great if your occasion involves a group with a lot of different tastes. You’ll find animal heads on the wall, fuzzy bar stools, and oversized, rather graphic paintings of food dominating the room. All that is cool, but mostly, we really like the food here, not to mention the very friendly service.
North Pond, in the middle of Lincoln Park, is like an extremely attractive person who never gets asked out because everyone assumes he or she is in a relationship. In practical terms, this means it’s a very good spot to snag a last-minute reservation. The space and view make you feel like you’re in a really nice cabin, and the seasonal American food is always outstanding.
There’s nothing understated about Maple and Ash. This steakhouse has chandeliers, candelabras, and a $145 tasting menu called “I don’t give a f*ck,” where the kitchen decides what you eat. It’s surprisingly versatile - it can support a large group or a quiet dinner for two. This is where you should eat when an occasion calls for going all out, and you want to do so in a space that feels like you’re in the November Rain music video.
RPM Steak is where to go if you’re looking for a scene - for instance, if you’re with a group of people from the suburbs who want a real night out in the city. It’s also a good choice if your dining companions happen to watch “E!”, since it’s part-owned by Bill and Giuliana Rancic. You might be skeptical of a spot with reality star connections, but the food is actually excellent, and the menu has a variety of small plates, salads, and seafood dishes that all deserve equal attention on your table.
This spot does upscale modern Italian, and feels pretty similar to RPM Steak. It’s particularly well-suited to bigger groups, with plenty of large tables and booths and a menu that’s great for sharing. Whatever else you get, make sure to order the house-made pastas. Extra points if your sister visiting manages to get in a Rancic sighting.
This warehouse-style Japanese restaurant is huge, and has an equally huge menu. It’s a great spot for a group celebration, especially if you settle in and commit to trying as many dishes as you can. It makes for an expensive, but very fun night.
The dimly lit space at Bavette’s has big comfortable booths, and jazz music that makes you feel like you’re in a speakeasy. It’s a French-style steakhouse, and everything on the very extensive menu is fantastic. It’s the kind of spot where you can get a $175 shellfish tower, followed by a prime rib sandwich. This versatile spot is great for an anniversary, or breaking in your new corporate card.
Every time we’re “over” Girl And The Goat, we eat here again and remember why reservations later than 4 pm are still hard to get. The food is delicious, and the menu is great for small groups who like sharing and don’t mind aggressively-titled dishes like “pig face.” If you’re feeling particularly ambitious, plan ahead and try to arrange for seats at the chef’s table.
Maude’s makes this list as long as you sit upstairs. Downstairs, where the bar is, it’s lively and more of a bistro, but the upstairs is quiet and somewhat romantic, with comfy booths and lots of candlelight. Maude’s does French classics like cassoulet, as well as “almost French” dishes like an onion fondue. Come here as a couple, or with a small group that isn’t afraid of onion breath.
Sometimes you want to celebrate in a nice neighborhood restaurant, and in that case, Riccardo Trattoria is perfect. It’s cozy and elegant, with great classic Italian food. Your server will most likely be charming, have a real Italian accent, and make sure you leave feeling special.