People want to hang out with you. Maybe it’s your great personality. Or maybe it’s your OK personality combined with the fact that you always know where to get good food. Either way, here’s where to go the next time you have to plan a group dinner last-minute. These restaurants have plenty of room, they’re relatively easy to get into, and the food is impressive enough that you can keep having an all right personality and still have friends.
River North is crowded. It’s full of people who work in the neighborhood, tourists staying in hotels, and Chicagoans who just decided to get off at Grand and walk around. Unfortunately, this popularity makes impromptu pre-going-out dinners difficult. But not if you know about Quartino. Yes, it will be busy and crowded, but you won’t have to wait long (or at all) thanks to the large number of dining rooms and tables. Plus, the small-plates-style Italian menu is full of reliably good food that’s very easy to share.
Going out for dim sum with a large group is ideal - after all, it’s almost impossible to eat everything you want to otherwise. And Minghin in Chinatown has you covered for all your large group dim sum needs. It’s huge, with tons of tables, and it’s open 365 days a year. Which is helpful to know about in case all your friends from high school are in town, and you need a place to eat on Christmas.
Sun Wah in Uptown is always crowded, but you shouldn’t be deterred from just walking in and trying for a table - you can usually get seated pretty quickly. Similarly, don’t let the fact that the Peking duck isn’t technically on the menu stop you from ordering it. It’s the best thing here, and it’s always available, even if you didn’t order it ahead of time. It’s carved tableside and served with bao, then as a rice or noodle dish, and finally as a soup. While the rest of the food here is hit or miss, it’s worth coming with a group just for the duck.
The West Loop is a lot like River North, in that it’s crowded and the best restaurants have long wait times. And while we’d never tell you Parlor had the best pizza in Chicago, it is perfectly tasty, and there’s also a long menu of satisfying bar food and salads that will please anyone who doesn’t (for some odd reason) want pizza. Plus, there are not one but two patios, so there’s always plenty of space for everyone to sit outside.
You were strolling along the 606 and began attracting followers like the Pied Piper, or the star of a musical’s slow-developing group number. So now you and all your new friends need a place to grab a casual dinner in Wicker Park. Head to Irazu. The large covered patio, BYOB policy, and awesome Costa Rican food make it perfect for a casual drop-in dinner. Just be sure someone stops by a liquor store before you get there.
We like to imagine that back in the covered-wagon days, settlers would stop the wagon train and eat together as a group. Maybe that was the inspiration for Frontier, which, as the name suggests, has a pioneer theme. Meaning there’s a lot of game on the menu, and pretty much everything is designed for groups to share. The all-season patio always seems to have seats available, and it’s way more hospitable than a poison ivy-filled meadow along the Oregon Trail.
Big picnic tables seem to be the universal smoke signal for a last-minute group dinner. And there are plenty of them on the patio at The Moonlighter. This place has an extensive menu of bar food like waffle fries, nachos, and burgers - and if it’s too cold to sit outside (even near one of their multiple outdoor fireplaces), just bring your group indoors. There’s plenty of space there, too, along with a lot of TVs. So this is an especially good choice if you or your friends like watching sports.
We have a lot of sushi restaurants in Chicago, but the really good ones aren’t always ideal for groups. They’re often too crowded (like Sunda), expensive (like Momotaro), or small (like Raisu). Not Sushi-san in River North. It has plenty of space, reasonable prices, and an upbeat atmosphere. We recommend focusing on the nigiri and sashimi (their “San-sets” come with an assortment of pieces meant for sharing) - and if not everyone is a big fan of sushi, they have lots of Japanese small plates that are great, too.
This casual Tex-Mex spot has lots of roomy benches and large tables. In fact, there’s a good chance you can come here with 10+ people and be seated right away, even for dinner. Get an order of the chili con queso (order extra tortilla chips - they’re excellent), along with fish tacos and any of their cocktails. After you’re done, feel free to walk around the block to see if you can lose some of your friends - nine other people is way too many to keep track of. Then circle back and and go downstairs to Lonesome Rose’s small basement bar, Golden Teardrops, for a quiet change of scenery.
Octavio is a Mexican restaurant that looks like it was dropped into Andersonville from River North, Wizard Of Oz-style. The space is huge, there’s loud music, and it has plenty of big booths and tables. There’s also a long list of tequila and mezcal, which makes this a pretty good spot for when you hit the point in your life where the effort of heading downtown isn’t worth being up past your bedtime. Plus, the food here is solid, with dishes like enchiladas, fajitas, and tacos made with fresh tortillas. Come here to eat, drink, and be in bed by 11pm.
Big wooden picnic tables are smoke-signaling again, this time at a West Loop barbecue spot. And since Green Street is popular and doesn’t accept reservations, you’ll need a solid strategy to eat here. Put someone in charge of scoping out the communal tables, and make sure they snag one as soon as it becomes available. Meanwhile, everyone else can get drinks at the huge bar in the center of the restaurant. If you’re feeling particularly efficient, a few of you can even get in line for food, since it’s served cafeteria-style. Basically, there’s nothing you can’t do when working as a team for the common goal of getting the meat sweats.
This is another pizza place that’s less about the food and more about having a good time with your friends. And like that friend from college who had the apartment everyone would crash at, Homeslice is here for you. The space is complete with big couches, swing sets that can fit more adults than seems possible, and another patio that has about a million tables. The pizza is actually pretty good, too.
Happy Camper in Old Town has the same kind of Peter Pan thing happening as Homeslice, which makes sense because they’re owned by the same people. But Happy Camper has more of a summer camp atmosphere, even though there’s no outdoor space (there are tire swings and an airstream trailer inside the restaurant). You shouldn’t have any trouble finding space, except in the airstream, which we guarantee will be constantly filled with people taking selfies.
The Loop is a minefield of bad (eating) decisions, so if you and your friends made plans to go ice skating and/or see the Trans-Siberian Orchestra together, but neglected to plan ahead for dinner, you made a big mistake. That’s how everyone ends up having dinner at The Corner Bakery out of desperation and hunger. Head to The Dearborn instead - it’s a fun, upbeat-but-not-too-casual spot with a well-rounded American menu. And make sure someone gets the cheeseburger - it’s really good.