Where to Dine with a Group in Chicago

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.

Noodles are the star of the menu here, but don’t be fooled. This warm, modern spot not only has space for your coworker crew and your out of town family, there’s also a wide-ranging menu to please all. After slurping down your own bowl of spicy seafood jjamppong, loaded with cuttlefish, shrimp, and pork, rotate plates around the table amongst your group. Everyone can get their hands on go-tos like barbecue pork buns, kung pao chicken, or even a few pieces of yellowtail sashimi. There’s also a whole Peking duck, served three ways, for a holiday feast to remember. 

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. 

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.

When your group is looking for a down-home Southern meal, Pearl’s Place is your best bet. The buffet format ensures no one leaves hungry, and the rib-sticking comfort food means you may end up sticking around from breakfast to dinner. Take your empty plate up (the buffet is available for all three meals) and the staff will load you up with fried chicken, shrimp and cheesy grits, or a slow-smoked ham hock dinner. For dessert, the peach cobbler, with its golden-brown crust and caramelized fruit, is non-negotiable, no matter how full you feel.

For beer lovers in search of upmarket environs to match terrific gastropub fare and interesting brews, this botanically inclined brewery is dressed for an occasion with dark woods and plenty of lush greenery. We especially love the private dining area that seats 15 to 30 at a large wooden table — and offers the full menu (and beers, naturally).