Wave Image
Don’t see your city? Drop us a line and let us know where you’d like us to go next.

Send Us Feedback

Thank You

We’re always looking to make The Infatuation the best platform to find restaurants, and we appreciate your feedback!
CHI

Guide

9 New Spots To Plan A Small Group Dinner

When you’re planning dinner with a small group, go to one of these spots.

Written by
9 Spots
Launch Map
9 Spots
Launch Map

When people who don’t spend a lot of time together decide to go out to dinner, you need a certain kind of restaurant: one that’s new enough to get excited about, and quiet enough for conversation - but not so quiet the entire room will hear you share the intricate details of your dog’s behavioral issues. Plus, you need tables that work well for small groups (bonus points if they’re round) and, of course, great food. And whether you’re getting together with friends who moved to the suburbs, former coworkers you haven’t seen since 2019, or relatives you recently discovered thanks to 23andMe, here are nine new restaurants to plan a dinner at right now.


The Spots

Gioia Ristorante E Pastificio

$$$$ 1133 W Randolph St

Quite frankly, our trip to Gioia was the inspiration behind this guide. This new Italian restaurant in the West Loop is just perfect for people who just want to have a conversation. It’s large without feeling cavernous, tastefully decorated in soothing neutral colors, and the service is on top of everything without being obtrusive. More importantly, the food is good. The focus is on handmade pastas, which include things like a fantastic bucatini cacio e pepe, pici with ragu, and paccheri mancini prepared tableside. And while Gioia is in one of Chicago’s busiest neighborhoods, it’s still easy to book a reservation. Plus, there’s a large bar area that’s great for hanging out after dinner, and a cute sidewalk patio with comfortable tables and chairs that don’t look like they were hastily purchased from a discount garden store.

Dear Margaret

$$$$
French  in  Lakeview
$$$$ 2965 N Lincoln Ave

If you’re looking for a leisurely spot where you can commiserate about your former boss, or discuss important topics like Aaron Rodgers’ contract, book a table at Dear Margaret in Lincoln Park. This charming BYOB French-Canadian restaurant in Lincoln Park has tasty dishes like foie gras terrine with fluffy milk bread, duck breast with lentils, and a friendly team who will leave you alone while you get to the bottom of how Aaron and Shailene met. In other words, it’s exactly the kind of place where you will want to take extra time to finish off that wine you brought.

Chikatana

$$$$
$$$$ 850 W Fulton Market

This Mexican restaurant in the West Loop is from a former chef of Mi Tocaya (one of our favorite spots in the city), and serves shareable dishes like cochinita pibil, tlayudas, tuétano, and pato en mole, along with perfectly chewy tortillas. The big space has large tables perfect for groups, the bar area is ideal for grabbing cocktails with friends (the Paloma is excellent). Another great thing to know about this place? They have a spacious sidewalk patio with plenty of shade.

Andros Taverna

$$$$
$$$$ 2542 N Milwaukee Ave

For someplace that’s popular and busy but not full of chaotic energy, check out Andros Taverna. This Greek restaurant in Logan Square is spacious, has great food, and you can usually get same-week reservations. Plus, that busy-ness means that the entire restaurant won’t hear your loud friend announce their divorce. In terms of food, you’ll find appetizers like the must-order kataifi cheese pie (shredded filo layered with cheese, baked, then topped with honey and pistachios), mezze spreads, entrees like prawn saganaki in a rich tomato sauce, and the best spanakopita we’ve ever had. They also have a big patio, weather permitting.

En Passant

$$$$
$$$$ 3010 W Diversey Ave

En Passant is a cute, casual new restaurant in Logan Square that’s full of delicious things. The escolar topped with black garlic honey is delicious (and made us realize how much we love black garlic honey), the chicken liver mousse is delightfully airy, and there’s an incredible smash burger topped with rose marie sauce and balsamic onions. The restaurant itself is small and dimly lit, with vintage touches (like chandeliers and candles) decorating the space. Right now they’re BYOB, so plan accordingly. And by accordingly, we mean stock up at Diversey Wine across the street.

Apolonia

$$$$ 2201 S Michigan Ave Chicago IL 60616 United States

You might already be familiar with S.K.Y in Pilsen, a fantastic restaurant that feels like a sexy basement. Apolonia, a mostly Mediterranean restaurant in the South Loop, is from the same team. Unlike S.K.Y., Apolonia is bright and airy, with tall windows and high ceilings. There are dishes like fantastic mussels on toast, a buttery truffle puff bread, and fiorentini topped with a rich pork sugo. This understated, minimally decorated place is where you go to catch up with your responsible friends who need to get home to the babysitter, or meet up with family who spent the day touring the Museum Campus. But no matter who you’re here with, dinner will be delicious.

Dr Bird’s

$$$$
$$$$ 1215 N Milwaukee Ave

This new Caribbean spot is the most casual restaurant on this list, and since they don’t take reservations you won’t have to worry about hunting down a reservation for five people within the next 24 hours. Luckily, it’s very easy to walk in, and the excellent food and laid-back atmosphere make it a great spot for a small group dinner. The original Dr. Bird’s opened in Buffalo in 1981, and their specialty are Jamaican patties. But the menu also has larger dishes like tender jerk chicken and creamy rasta pasta with Gruyere, rosemary, and roasted tomatoes. The sides are outstanding too - including must-order coco rice that’s sweet and savory, and festivals that are a perfect complement to the smoky jerk seasoning. Bird’s also has a long list of rum cocktails, and incredibly friendly service. In other words, bring some friends and order everything.

Matt Haas

Rose Mary

$$$$ 932 W Fulton St

Rose Mary is a new Croatian spot in the West Loop and reservations are hard to get. But if you have a few weeks (or a couple of months) notice, you should go ahead and book a table. The food is fantastic, with dishes like a tomato, farro, and asparagus salad, crni rizot topped with grilled squid, and of course, incredible pastas. Plus, the service is great (no need to send a search party out for your server) and the overall feel of the place is happy and upbeat.

Avec River North

$$$$ 141 W Erie St

Do you love Avec in the West Loop, but know that the cramped, communal seating situation is not ideal for privacy, and you probably won’t be able to make a reservation until 2023 anyway? Then check out Avec’s River North location. It’s about 56 times larger than the original Avec, isn’t shaped like a shoebox, and everyone gets their very own seat. Plus, it has a longer menu full of Avec classics (like the chorizo-stuffed bacon-wrapped dates and taleggio flatbread), along with a lot more small and large plates, pastas, and pizza.

You'll need a better browser for that!
Upgrade to Chrome and start finding Restaurants.