The Most Fun Dinner Places in Chicago

If you’re looking for a polite meal, click now. This guide is for anyone who’s ever wondered “where’s the place?” and has a penchant for mid-dinner photo-taking and bar-hopping after dinner. Chairs aren’t the only thing at some of these restaurants, and while the food is important, having a good time is paramount. These restaurants range from new spots that are flooding your feeds to classic haunts where successful meals are determined by the number of old-fashioned drinks you have with the bartender. They may not all be the best new restaurants in town, but you’ll always walk away with a story or two.

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La Serre is a fun French-Mediterranean spot in Fulton Market with just the right amount of flowers and speakers. It’s loud but never overwhelming, and the shareable dishes are thoughtful despite the large mirrors that say cheesy things like “Merci Beaucoup.” The creamy angel hair pasta is worth the suggested 15g caviar on top, and other less expensive classics like raw tuna and beef steak are more than satisfying. Combined with the massive bouquet in the center of the dining room, La Serre has the feel of a wedding, without the immediate threat of meeting strange cousins.

Brasero restaurant seems to specialize in throwing parties every night. This Latin-American spot in West Town is great for convivial gatherings of all sizes, with a mix of shareable dishes like fried quail and grilled half-lobster, and catchy bossa nova music that practically begs you to come along with the best chatter to match the secluded space and fun atmosphere. But Brasero's food is just as enjoyable, with almost everything striking a balance between sweet and spicy. The moqueca dish has the perfect amount of chili to enhance the coconut broth, mahi mahi and shrimp. Whatever you order, you'll all leave with a slight smell of smoke, thanks to the wood-fired grill in the back and the constantly popping fireworks.

If there's anything the loud music pouring down the Fulton Market sidewalk indicates, it's that Costera loves to party. The extensive use of thatch, palm trees and basket lights leans into the Tulum theme, while the dim lighting and loud DJ sets prove that Clubstaurant 101 has been taken. You're not really here for the food – it ranges from good tacos to flames on the table that turn into disappointment. jam. Stick to drinks and those tacos or quesadillas (they're the least annoying). And if you're here after 11pm on weekends, it gets even livelier with bottle service starting and plane trays filled with potions and sparklers.

Borscht is warm and comforting. It’s also fun when you’re at Anelia. This Ukrainian restaurant in Avondale is exciting even before you sit down. Waiters scurry around with gleaming zakuski carts filled with appetizers. Upbeat electronic music plays in the background while flower-like lights give the dining room a colorful glow. Once you’re ready to order, the waiters trumpet the menu as if they’re narrating a video filled with haluski and kofbasa. And you will, too. Everything is delicious—from the aforementioned beet soup with stewed pear and duck to the creamy pastries stuffed with potatoes and pork.

Provaré is a great place. This bright, Creole Italian restaurant has an R&B playlist that will remind you of Usher’s ’90s greatness, offers free drinks as soon as you sit down, and serves food that will make you raise your hand to silence the table so you can enjoy a private moment with homemade pasta. Signature dishes include fried lobster tails, a creamy chicken parmesan that’s the antidote to Apple’s dreaded news, and a tender lamb chop that pairs perfectly with a side of spicy burnt corn. The place is busy but never chaotic, and there’s a good chance the chef will be on hand to bring out dishes and make sure you’re having a good time.

Limited hours. No reservations. An unpredictable list. Normally we'd consider all of these red flags, but we're here to tell you that the line out the door is worth the wait. Since they are open until 2am, the wait can be quite long. The menu changes every day, and it's exciting at the same time – “This slope pasta is incredible!” – and bittersweet – “Will I ever see miso butter scallops again?” The Warlord plays hard to get, but it makes us want this place even more.

A quick online search for Adalina will show you a sea of ​​white tablecloths and a menu full of pasta and veal Parmigiana steaks. You won't realize how much fun Adalina is until you spend a few minutes in this upscale Italian restaurant, sitting on rumpled velvet chairs and surrounded by flower paintings that would make Georgia O'Keeffe suspicious. The bar fills with people hanging out two hours before (and after) their reservation time, and the sumptuous dining room gets louder and noisier throughout your meal. People from different tables will inevitably start mingling with each other, someone might fall on their heels, and things usually evolve into a nice nonsense show.

There is nothing understated about Maple and Ash. It has chandeliers, candelabra, and an optional $200 tasting menu called “I Don't Give Any Away,” where the kitchen decides what you eat. This is a wonderful and surprisingly diverse restaurant that can support a large group or a quiet dinner for two. This is the place to eat when an occasion calls for you to go all out, and you want to do so in a space that looks a bit like the palace in Bram Stoker's Dracula. The one from the 90s with the Keanu Reeves and Gary Oldman hairstyle that looks like an ass.

This guide is specifically for places like Meru, and let’s count the ways. This Japanese restaurant is located on the rooftop of the $700-a-night St. Regis Hotel on Lakeshore East. The skyline view is incredible, and the service is even better. The food isn’t great (the long menu ranges from perfectly acceptable sushi to not-so-great entrees like seared cod), but great food isn’t why you’re here. It’s about enjoying the view, having a few drinks and dessert, and feeling like you can throw money off said rooftop.

This Greek restaurant in the West Loop is the size of a football field, it’s packed, it plays loud music, and it serves dishes that regularly appear on TikTok. Reservations are required for 10 p.m. because at midnight they hand out white napkins for everyone to circulate around, waiters come out singing and waving flares, and the entire restaurant turns into a club. While some of Lyra’s menu can be hit or miss, the crispy spinach and tender lamb ribs are delicious enough to help you overlook the restaurant’s shortcomings, especially if you like fireworks and being surrounded by an abundance of bamboo lampshades.

Dining at Ummo feels like hanging out in a friend’s loft apartment—if your upstairs friend (or maybe squat?) also made fresh pasta. Colorful, framed posters cover every inch of the walls, while lively funk and soul music fuels the open space. That excitement carries over to the food. Couples excitedly crack open playful tomato-shaped desserts filled with raspberry compote, or split delicious plates of lobster ravioli. At a larger table, another group starts the night with a dry-aged steak drizzled with a refreshing green bagneto. And when you’re on a second floor with a DJ, pool table, and plenty of couches to lounge on, there’s no reason for the party to stop after a cacio e pepe.

This Italian steakhouse on the edge of Fulton Market does its best to give the place a mid-20th-century flair, with waiters wearing jackets and serving up refreshments. But Fiorita Restaurant offers the most delicious dishes and cuisine. There are excellent steaks on the menu, like an olive-fed New York Wagyu steak that will make you wonder if that cow traveled on a private jet after a weekend stop in Portofino on its way to Chicago. Strong drinks and live music on the weekends contribute to a lively atmosphere and make this a great place for special occasion dinners.

Any Chicago restaurant that comes to mind when you associate the words “West Loop,” “Italian,” and “Boca Restaurant Group” is likely a fun place to be. That’s the case with Alla Vita, an Italian restaurant in Randolph. Designed to please everyone, from couples to large groups in town for a conference, it’s also pretty, decorated with hanging plants and an interesting overhead installation that looks a bit like fish gills. And while the menu won’t blow you away with creativity (it’s basically pizza, pasta, and a handful of antipasti), what it does have is good. The pizzas have a chewy, wood-fired crust, and the silky cacio e pepe ricotta pies will have you waving a spoon in the air like a Yoplait commercial from the 2000s.

Although Obelix wasn't very popular when it first opened, this spot on the North River is now one of the most sought-after dinner spots in the city. At first glance, Obelix looks like a typical French restaurant, but it is not. He walks a tightrope of being formal without being pretentious. That same balance is found in the food, which is filled with a mix of classics like escargots and fun fusion things like foie gras tacos.

After a brief closure, the excellent veggie-focused Midwestern pasta spot has reopened in a new, larger space. The menu isn’t much different, save for a new section for things like lamb shanks and salmon collars. But the larger dining room (and new chef’s table and large bar) means Daisies is packed by 6 p.m. even on a random Wednesday. Make a reservation in advance, and nibble on pierogi while listening to a cheerful soundtrack of R&B and the faint roar of other guests’ conversations.

A great soundtrack that’s full of life and soul, delicious food, and a long wine list are just a few reasons why you’ll want to spend as much time as possible at Bronzeville Winery. This American restaurant also has the perfect mix of loud music and noise to keep everyone in the dining room from hearing why your friend thinks health insurance is actually a form of gambling.