Where to Dine with a Group in Chicago

In the heart of Pilsen, chef-owners Thai and Danielle Dang serve large-format Vietnamese plates made for the center of the table, with everything from tender grilled pork shoulder and Australian wagyu to jumbo prawns and oysters. Despite the shareable plates, you should be ready to fend off your fellow diners when the restaurant’s famous crispy chicken wings arrive. Or, you could make sure there’s enough for everyone by booking one of HaiSous’s semi-private or fully private event packages, which can comfortable seat up to 45, with customizable menu options, its own sound system, and satellite bars.
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For a casual dinner that feeds a crowd, you can’t go wrong with pizza. Homeslice Pizzeria and Patio in Lincoln Park lets your group spread out with its all-seasons patio and kick back with a quintessentially Chicago dish— thin and crispy tavern-style pizza. Whether it’s game day, happy hour, or just a casual night out, you’ll want to order a little bit of everything for the table. Mozzarella bread sticks and specialty pies like the hot-honey topped Nadene or birria pizza with consommé will keep your group reaching for just one more slice.

If your group is looking for a dose of summer in the depths of a Chicago winter, head to Casa Tulum, which brings the tropical warmth of a Mexican beach town to the South Loop. Along with the bright, coastal vibes, Casa Tulum serves modern Mexican food with flair, including several seafood-forward specialities. Try the shrimp diabla, coated in a fiery sauce and served with cilantro-lime rice; or the cubetazo, a sort of cheffed-up seafood boil with crab legs, mussels, and head-on shrimp. Don’t skip the cocktails, which keep the tropical theme going with plenty of pineapple, mango, and coconut-infused creations. 

As its the name implies, family and friends will feel like they’ve stepped off Randolph street and right into the Alhambra Palace in Granada, Spain. From the outside in, the Chicago version decor channels Moorish style, with gilded doors and window frames, mosaic tiles, and crystal chandeliers dangling from lofty ceilings. The menu offers Middle Eastern crowd pleasers like hummus, falafel, and a variety of kebabs, including vegan options; all available in family-sized platters to share around the table. Plus, the rotating schedule of belly dancers and Latin dance nights should keep your group entertained well past dessert.

When the group chat is in the mood for a parade of pasta, Monteverde in West Loop delivers, with handmade noodles crafted behind a glass-enclosed pastificio. Your group can watch as what might be their own pasta order is rolled, shaped, and filled right in front of them. Larger parties should order multiples of house favorites like Cacio Whey Pepe with fresh summer truffle and gnochetti with pesto, so everyone can try a bite. With their variety of shapes, sauces, and textures, these entrees are meant to be mixed, matched, and shared. And if you can, do save room for dessert – the butterscotch budino, with its crisp brûléed top, will end any group outing on a high note.

Nestled down a cobblestone courtyard in the West Loop, Trivoli Tavern hits a sweet spot between high-class and comfortable. The warmly lit restaurant has a cozy and welcoming vibe, while the menu provides a rare opportunity for seafood lovers, pasta fanatics, and steakhouse traditionalists to all walk away happy. The restaurant has also built a strong following for its drinks, where classics like a Vesper are executed with finesse, while wine and beer options easily find their match with any meat or pasta dish that makes its way to the table.

Carnivale was built to accommodate groups. The vibrantly colored West Loop institution pairs a high-energy dining room with Latin-inspired food that pulls from Central and South American influences. The menu rewards sharing with entertaining options like tableside guacamole and tuna poke to larger-format favorites like paella de mariscos loaded with seafood and wood-grilled arrachera steak. The setting is just as memorable: brightly colored lanterns, original artwork, soaring ceilings, and a ton of visual flair surround the tables in the massive dining room. If your group is large enough to require more than a standard reservation, Carnivale excels with its range of semi-private and private event spaces for everything from an intimate gathering to just about any celebration that deserves a little extra fanfare.
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Park and Field knows how to keep a group happy, year round. When temperatures drop, the casual space fires up the indoor fireplaces and outdoor firepits on its massive open patio, upping the cozy quota across the board. During the week, come for a crowd-pleasing menu that covers everything from burgers to grain bowls. And on weekends, a bottomless brunch buffet takes over the space, complete with a live omelet station. Come here with the whole family, or your booziest friends.

With an open patio, tire swings, and an actual camper van on-site, Happy Camper might seem like a strictly summer locale, but the twinkly lights and hot pizza only get cozier in the holiday season. A full menu of tavern-style pies means friends and family will experience the joy of a  thin, crispy pizza, cut into squares, the way real Chicagoans like their pie. The Nadene, topped with pepperoni, ricotta, basil, and hot honey, comes together to create a sweet and salty delight, though you can always make your own or dip into soups, salads, or wraps instead.

Smoke Daddy is, simply put, the best place to hang out before catching a game at Wrigley Field. The longtime smokehouse has all the space and casual energy you need from a pre or post-game meal, whether the Cubs win or lose. Order family-style with the Taste of the Daddy platter, which ensures everyone gets a taste of all the meats — that includes brisket, pulled pork, ribs, smoked chicken, and comfort food sides like mac and cheese, pit beans, coleslaw, and pickles. Between bites of saucy chicken wings and generous pours of beers, you should know that Smoke Daddy is a place for lively conversation, not white tablecloths and polished tasting menus.
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When the restaurant’s motto, “Hoy por tí. Mañana por mí,” literally translates to “Today for you. Tomorrow for me,” there’s no question your group will be treated like family. There’s room for all in the 5,000-square foot space, not to mention the rooftop bar, with a retractable canopy and heated lamps for winter. La Josie has brunch, happy hour, dinner and even Taco Tuesday covered. Plus, the three agave bars are stacked with mezcal and Tequila flights for everyone from newbies to true connoisseurs. Bring a group and tuck in to ceviches, enchiladas, and a must-order molten queso fundido, made with a blend of three cheeses and housemade chorizo.

Dinner here means dining in ornate, sun-filled rooms with a gorgeous view of the Chicago River as your backdrop. The menu here is made for sharing among large groups — think plates of feta-stuffed dates, grilled octopus and hummus, kale and avocado dip, and a Lebanese lamb feast, complete with sides like pistachio tzatziki, turmeric pickled cauliflower, cucumber salad, hummus, and grilled pita. Taste a little bit of everything while you lounge on daybed-style seating at this boho-chic, Mediterranean escapist fantasy.

Travel can be difficult during the holiday season, so why not bring the flavor of France a little closer to home? Le Sud’s menu has Southern French vibes baked right in — take, for example, the grilled swordfish with fondant potatoes, mushrooms, and peas in a herby butter sauce; or the sharable croquettes, filled with smoked ham, Gruyere cheese, Herbs De Provence, and a garlic aioli. This rustic French cuisine can be enjoyed year round on Le Sud’s enclosed, heated patio, which fits up to 60. Choose from the well-stocked French cellar, or pay a $35 corkage fee to BYO. 

The vintage vibes at longstanding cocktail bar and restaurant Club Lucky unite all over their signature item — the Killer Martini. Each oversized pour of the classic cocktail has its own unique flair, including a holiday-appropriate Sleigh Ride, a mix of Rumchata, Amarula, Captain Morgan’s Spiced Rum with a cinnamon sugar rim, and a chocolate cigarette garnish for kicks. Come for the knockout martinis, but stay for the old-school Italian cooking (spaghetti and meatballs, lasagna bolognese), in a dining room that was once home to a hardware store and Prohibition-era speakeasy. You can take over the cocktail lounge or patio, or rent out the private dining room for groups of 20-45. 

Dietary restrictions should never keep your crew from enjoying a meal together, and PLANTA Queen makes sure of that. The upscale restaurant’s lush greenery and spacious layout is perfect for groups, and the completely plant-based, Asian-inspired menu doesn’t hold back on flavor. Order big for the table and share plates of bao filled with savory “chicken” mushroom pieces coated in a crispy batter; gluten-free Singapore noodles with curried vegetables; or a selection of traditional and more nouveau maki rolls. There’s also brunch and a kid’s menu, should your group include little ones. 

Outfitted like a literal castle with chandeliers, a throne, candelabras, and gold trimmings all around, King of Cups bar is anything but low-key. While you take in the fanciful decor, sip an appropriately royal libation like the Winter King, a flaming drink with rum, cachaça, Alchermes Liqueur, lime, banana-pecan-date orgeat, and grapefruit. Or, if your group is happy to share, the Kingdom of Stars packs enough of a literal punch for six. If the grand cocktails aren’t enough to keep you entertained, King of Cups also plays host to nightly tarot card readings. Bring your friends for a boozy post-dinner celebration, but eat beforehand, as this spot is strictly for clinking chalices. 

For the group that isn’t too concerned about getting a little messy, Babygold Barbecue in Berwyn has the sauce you want. Just outside the city, this casual smokehouse serves classically filling barbecue options like pulled pork sandwiches, baby back ribs, and macaroni and cheese. The so-called “Mac Attack” is made with pimento cheese and comes topped with pulled pork, chopped brisket, hot links, bacon, or chicken. While offerings, naturally, lean toward the carnivorous, barbecued cauliflower is available for plant-based pals. Either way, there won’t be an unused napkin in sight. Plus, if your crew is ready to make it a night on the town, pop over to the live music venue next door, Fitzgerald’s.