There are approximately 865,789 bars in Chicago, and we would probably have more if the city weren’t so stingy with liquor licenses. So in general, you have lots of options. But when you’re celebrating a special occasion, you need someplace fancier than the bar where you normally go to yell about sports or hang out with friends every Friday night. Here are 12 places you might want to get a little dressed up for, all of which work for a variety of celebratory things - whether it’s a birthday, an anniversary, or even just a night when you want to yell about sports in a top hat.
For Chicago, The Aviary in the West Loop is the special occasion cocktail bar. It’s from the same owners as Alinea, and you’ll find elaborate, Alinea-esque drinks on the menu here. Cocktails start around $28, and vary in the amount they look like science experiments. For example, The Jungle Bird has little clear tapioca-like balls filled with rum that pop in your mouth, and the Old Fashioned goes even further - it comes in a ball of ice you need to snap with a rubber band. You can make reservations, but you can also walk in (there might be a wait, but that will give you some time to quickly reread your eighth grade science textbook).
Many of the bars on Hubbard Street in River North are loud, crowded places where you wander in, order a drink, get bumped into by tourists, and leave. Not Celeste. This place has four levels, each with its own distinct atmosphere, and for a special occasion we suggest the top two - the third floor is a little swanky, with chandeliers and a couple curtained booths for groups, and the rooftop level feels kind of like Pan’s Labyrinth, with plants and marble tables all around. If you happen to be coming from a Saturday Night Fever costume contest (which you won), though, celebrate with a trip to the disco floor.
This bar is right next to the Peruvian restaurant Tanta, and owned by the same people. Arbella is fancy without feeling stiff - drinks are on a map-like cocktail list that looks less like a menu and more like something that would come in the box of a Carmen Sandiego board game. The cocktails are inspired by various countries on that map, like the “PB&J” (peanut butter infused vodka and jelly ice) for the US, or a “snow cone” with sake, pisco, and Red Bull syrup for Antarctica. Get a drink or two before heading next door for dinner.
Hotel bars are convenient places to meet up when people are visiting from out of town, but many have about as much personality as a doctor’s office, and are only good for killing time before you head someplace you actually want to be. That’s not the case with Devereaux, the rooftop bar at the Viceroy (also home to Somerset, one of the best restaurants in Chicago). This place has an upscale art deco atmosphere, and in the summer they open the terrace. Plus, you can get snacks and small plates from Somerset’s kitchen - making this a more enjoyable place to stand around in your dressy clothes than most other spots in the Gold Coast.
This River North spot is definitely themey - it’s a tiki bar serving tropical cocktails in mugs shaped like pineapples, conch shells, and mermaids, among other things. It’s a good place to go before your Super-Bowl-winning trip to Disneyland, because your (very generous) friends can buy you the $385 “Treasure Chest,” a cocktail for 6-8 people that will get you mentally prepared for the the Pirates of the Caribbean ride.
If you’re a fan of Clue (or any other movie that takes place in the 1950s), you’ll appreciate the Game Room in the Chicago Athletic Association Hotel. This place looks like it belongs in an old mansion, with big leather seats, billiards tables, and a bocce court. It serves well-made classic cocktails, and is a good first stop on the long road toward convincing your friends to do that live-action Murder Mystery game with you.
This is an eight-seat bar that’s also in the Chicago Athletic Association Hotel. You need to buy tickets for a seating here (they’re $50, but the price goes towards your drinks), and there’s a two-hour time limit on your seating. They serve cocktails (made with very rare vintage scotches and other spirits) omakase-style, and the bartender will tailor yours to your preferences. Unless your preference is for very cheap well liquor, in which case, you’re probably not finding this guide very helpful so far.
If you want a little of the sceniness of River North without going too far, Pops For Champagne is a good choice. You’ll find a long menu of sparkling wine, champagne, and champagne cocktails, and the atmosphere is lively but still formal. The decorations involve a lot of candles and glass, which is a good thing for two reasons: 1) it makes the space look nice, and 2) it discourages dancing. (There are plenty of other places around where you can dance when you’re done.)
The Violet Hour in Wicker Park is a good destination cocktail bar from the people who own Avec and The Publican. This place might seem like it’s trying hard to be cool - from the unmarked door to the “House Rules” (which ban baseball caps, Cosmopolitans, and any drink that’s a -bomb, jager or otherwise). It doesn’t come off as obnoxious, though, because the craft cocktails really are good. Inside, it feels like a lounge more than a bar - it’s dark, with lots of candlelight, plus comfy chairs and tables that can be sectioned off for privacy. Overall, not a bad spot to celebrate the launch of your top-secret baseball-cap-recycling startup.
There’s a good chance your celebration will take you to the West Loop, since that’s the Disneyland of restaurants. But all those fun, popular spots mean the neighborhood is usually full of people. When you want to avoid those people, head to the Press Room. It’s a quiet wine bar where it’s almost always easy to get a table. They have really good cocktails, a great selection of wines, and a short small plates menu. Put this on your itinerary if you have reservations at a restaurant with the word “goat” in its name.
Bordel is from the same people who own Beatnik, and this cocktail bar is equally over-the-top with its atmosphere. It’s supposed to be a cross between a bordello and a speakeasy, so decor-wise, you can expect a lot of velvet and tassels. The drinks here start at around $13, and the menu includes things like a Oaxacan Old Fashioned (with mezcal and chocolate bitters) and a “campfire nog” with peated scotch and an egg.
Even though it’s well-known (especially as a spot for pre-wedding get-togethers), Drumbar still feels like nobody has discovered how nice it is. It’s on the rooftop of the Raffaello Hotel, which is in a non-crowded section of Streeterville. The menu has an extensive selection of bourbon, whiskey, scotch, and cognacs, and drinking here feels like hanging out in a private club - one you actually want to be a part of.