The Most Fun Dinner Spots In Chicago guide image


The Most Fun Dinner Spots In Chicago

A night out at one of these restaurants will never be boring.

Those seeking a polite meal, click away now. This guide is reserved for anyone who’s wondering, “Where’s the place to be?” and might have a penchant for mid-dinner photoshoots and post-dinner bar hopping. Chairs aren’t just for sitting in some of these restaurants and, while food is important, a good time takes priority. They range from new spots flooding your feeds to classics where successful meals are determined by how many Old Fashioneds you drink with your server. These places may not all be the best new restaurants in town, but you'll always walk out with a story or two.



Limited hours. No reservations. An unpredictable menu. Warlord opened in May with little information beyond the above, which we normally consider red flags. But we can now tell you that the line out the door is worth the wait. And since they're open until 2am, that wait can be a pretty long one. The menu changes everyday, which is both exciting—"This ramp pasta is incredible!"—and bittersweet—"Will I ever see these miso butter scallops again?" Warlord is playing hard to get, but that only makes us want this spot even more.

A quick online search of Adalina will show you a sea of white tablecloths and a menu full of pasta and veal chop Parmigiana. You won’t realize how fun Adalina is until you’ve spent a few minutes at this upscale Italian restaurant, sitting on crushed velvet chairs and surrounded by flower paintings that would make Georgia O’Keeffe suspicious. The bar is filled with people hanging out two hours before (and after) their reservation time, and the posh dining room gets louder and louder through the course of your meal. People from other tables will inevitably start to mingle with other tables, someone might topple over in their heels, and generally things devolve into a good-natured sh*tshow.

There’s nothing understated about Maple and Ash. It has chandeliers, candelabras, and an optional $145 tasting menu called “I don’t give a f*ck,” where the kitchen decides what you eat. It’s a great restaurant that’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 kind of like the mansion from Bram Stoker’s Dracula. The one from the 90’s with Keanu Reeves, and Gary Oldman’s hairstyle that looks like a butt.

This guide exists specifically for places like Miru—and let us count the ways. This Japanese restaurant is on the rooftop of the $700-a-night St. Regis Hotel in Lakeshore East. The view of the skyline is incredible, and the service is even better. The food isn't amazing (the long menu ranges from just-OK sushi to not-very-good entrees like burnt miso cod), but great food isn't why you're here. It's to admire the view, have a bunch of drinks, feel like you can afford to throw money off said rooftop.

This Greek Restaurant in the West Loop is the size of a football stadium, crowded, plays loud music, and has dishes that pop up regularly on TikTok. 10pm reservations are coveted because at midnight they pass out white napkins for everyone to wave around, servers come out singing and waving sparklers, and the entire restaurant turns into a club. While some of Lyra’s menu can be hit or miss, the flaky spanakopita and tender lamb ribs are delicious enough to help you forgive the restaurant’s flaws, especially if you love pyrotechnics and being surrounded by an absurd amount of wicker lampshades.

Eating at Ummo feels like hanging out in a friend’s loft apartment—if your loft-owning (or potentially squatting?) friend also made fresh pasta. Colorful, framed posters cover every inch of the walls, while energetic funk and soul music fuels the open space. And that excitement carries over to the food. Couples are enthusiastically breaking open a playful tomato-shaped dessert full of raspberry compote, or splitting tasty bowls of lobster ravioli. At a larger table, another group is kicking off the night with dry-aged steak drizzled with tangy bagnetto verde. And when you throw in a second floor with a DJ, pool table, and lots of couches for lounging, there’s no reason the party has to stop after the cacio e pepe.

This Italian steakhouse on the edge of Fulton Market is working hard on channeling mid-century-era glamour, complete with servers in jackets and a humidor. But Fioretta delivers on style and substance. There are excellent steaks on the menu—like an olive-fed wagyu New York strip that will have you wondering whether that cow got to fly on a private jet with a weekend stopover in Portofino on its way to Chicago. Strong drinks and live music on the weekend contribute to the buzzy vibe and make this spot great for a special occasion dinner.

Any Chicago restaurant associated with the words “West Loop,” “Italian,” and “Boka Restaurant Group” is probably going to be a good time. This is the case with Alla Vita, an Italian spot on Randolph. It’s designed to be a crowd-pleaser, buzzing with everyone from couples to large groups in town for some conference. It’s also pretty, decorated with hanging plants and an intriguing overhead installation that looks a little like fish gills. And while the menu isn’t going to blow your mind with creativity (it’s mainly pizza, pasta, and a handful of entrees) what’s on it is good. The pizza has a chewy wood-fired crust, and the silky cacio e pepe ricotta dumplings will have you waving a spoon in the air like a 2000s Yoplait commercial. 

The hype surrounding this River North spot has been of the slow-burn variety. It didn’t open to much fanfare in the summer of 2022, but has steadily become one of the most sought-after dinner reservations in town. On the surface, Obelix looks like a typical, white-tablecloth French restaurant. It’s not. Obelix walks the tightrope of feeling formal without being stuffy. And that same balance is present in the food, which is filled with a mixture of classics like escargot and playful, fusion-y things like a foie gras taco.

After a short closure, this excellent vegetable-centric "Midwestern pasta" spot reopened in a new, larger space. The menu isn’t that different, aside from a new section for things like lamb shank and salmon collars. But the the bigger dining room (and the new chef’s table, and large bar) means that Daisies is packed by 6pm even on a random Wednesday. Make a reservation in advance, and eat pierogies while listening to an upbeat R&B soundtrack and the dull roar of other diners’ conversations.

Google “Monteverde” and try to make a reservation for some time over the next month. Did you hear that? That was Resy laughing at you. This incredible Italian restaurant has been a guaranteed good time since it opened in 2015, and is the first place we try (and often fail) to make reservations when someone from the East Coast tells us they're visiting. The menu is full of hits, from cacio e pepe to the ragu alla Napoletana—a tomato-braised pork shank with three soppressata meatballs, two cacciatore sausages, and a pile of fusilli we want buried with us when we die.

Because of its fantastic funk and soul soundtrack, delicious food, and long wine list, there are plenty of reasons to hang out at Bronzeville Winery for as long as possible. This American restaurant also has the perfect combination of loud music and conversational buzz that prevents the entire dining room from overhearing why your friend thinks health insurance is technically a form of gambling. Plus, there’s a great sidewalk patio.

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The Most Fun Dinner Spots In Chicago guide image