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The Casual Weeknight Dinner Guide

The 15 best places for a casual weeknight dinner.

Written by
15 Spots
Launch Map
15 Spots
Launch Map

It’s Wednesday night. You could spend your time at the grocery store, passive-aggressively counting how many items everyone else in the express line has (naturally, you have exactly 15) - or you could go out to eat. You need a spot that’s weeknight-appropriate, though: easy to get into, not too expensive, and casual enough that you can show up in whatever you’re already wearing. Here are 15 of our favorite spots for a midweek meal.

All restaurants featured on The Infatuation are selected by our editorial team. The Casual Weeknight Dinner Guide is presented by the American Express ® Gold Card. Click here to learn more about the benefits and rewards you get from paying with the Amex Gold Card while dining out.

The Spots

Sandy Noto

Cafe Marie-Jeanne

$$$$ 1001 N California Ave

This cafe in Humboldt Park is the perfect place to pretend you’re a townsperson from the French village in Beauty and the Beast. You can order everything from calf brains on toast to duck frites, with lots of smaller plates (like smoked or pickled fish) to round things out. Come here on your own and sit at the bar, or meet a few friends after work for a civilized but not absurdly expensive meal.

Mi Tocaya Antojeria

$$$$ 2800 W Logan Blvd

Mi Tocaya is exactly where you want to be after a long day at work. The friendly service and fun atmosphere make it relaxing, and the Mexican food is delicious across the board. Get the peanut butter e lengua (beef tongue with peanut salsa), the albondigas, some tacos, or whatever else appeals - it will all be very, very good. And you’ll enjoy it even more if you’re sitting on the outdoor patio.

Sandy Noto

Raisu Japanese Fine Dining

$$$$ 2958 W Irving Park

This small spot in Albany Park serves a menu of high-quality sushi that varies depending on what’s been flown in that day. Meet up with friends and share a few rolls, along with some pieces of delicious (and affordable) nigiri and sashimi. Eating solo at the sushi bar is also a great idea.

Bar Roma

$$$$ 5101 N Clark St

Head to Bar Roma for great Italian food in a space that feels cozy, despite actually being pretty big. There’s a huge, welcoming bar right when you walk in, and we’ll understand if you decide to stop there. But the main dining room, decorated with reclaimed wood and old furniture, feels laidback and inviting even when it’s busy. Focus on the pastas (like the cacio e pepe), all of which are made in-house, and don’t ignore the daily specials.

Sandy Noto

Little Bad Wolf

$$$$ 1541 W Bryn Mawr Ave

Few things are better in the middle of your week (or anytime, really) than an excellent cheeseburger, and this bar in Andersonville has one of our favorites. It also has other food that’s a lot more interesting than what you’ll find at your typical neighborhood drinking spot. Order one of their light and fluffy bao (the pork is our favorite), or a salad so big it could easily feed four people. Because Little Bad Wolf understands that sometimes you want to eat a salad that seems less healthy than a burger.

Sandy Noto

Maillard Tavern

$$$$ 494 N Milwaukee Ave

Speaking of burgers, they’re the focus at Maillard Tavern in River West. There are a number of different versions, and they all work really well. The classic (with lettuce, tomato, onion, ketchup, and pickles) tastes like what you might imagine a roadside burger from the 1950s to be, but there are also more complicated options, like one with foie gras and truffle that’s delicious, if very rich. The space is small, with wooden booths, tables, and a large bar. Come here with a small group, or even just by yourself for a quick meal.

Christina Slaton

Wyler Road

$$$$ 3581 W Belden

We’re still trying to find a time of the week when we don’t want to go to Wyler Road. It feels like a cool cafe-bar hybrid, and it’s ideal for grabbing dinner and beer with some friends. All of their sandwiches are good, but the best strategy is to go with options you might not find anywhere else, like the crawfish melt. And you’re going to need a side of cheese curds every time. Trust us on that.

Sandy Noto

La Josie

TacosMexican  in  West Loop
$$$$ 740 W Randolph St

When you want to have a miniature Saturday night in the middle of your week, go to La Josie in the West Loop. It has three full bars and a rooftop deck, and while all these areas are lively, you still won’t feel like you’re out having dinner in the club. Order a few tacos (all on housemade tortillas) and a cocktail from the extensive tequila list. The servers and bartenders are really friendly, and will help you forget that your work week isn’t over yet.

Sandy Noto

Spacca Napoli

Pizza  in  Ravenswood
$$$$ 1769 W Sunnyside Ave

This Ravenswood spot is one of our favorite pizza places in the entire city. It serves authentic Neapolitan pizza, cooked in a wood-burning oven until the crust is perfectly bubbly around the edges. You can’t go wrong with any of the pies here, and the space feels comfortable and laidback no matter how busy it gets. If you can score a seat on the outdoor patio during the warmer months, even better.

Big Jones

$$$$ 5347 N. Clark St.

Big Jones is a Southern restaurant in Andersonville with a focus on old-timey recipes (like “Chicken and Dumplings Circa 1920”) and fantastic fried chicken. But our favorite things here are the seasonal dishes, like chestnut spaghetti and curry peanut bisque. They recently remodeled, so while you’ll still feel like you’re eating in a Southern living room, it’s now a living room with an open kitchen.

Sandy Noto

Pizzeria Bebu

$$$$ 1521 N Fremont St

Bebu is in the part of Lincoln Park that consists mainly of chain stores and unpaved parking lots. So while it isn’t particularly scenic, the lack of foot traffic means you won’t have to wait for a table during the week. And the Neapolitan-style pizzas here are outstanding. There’s a mix of signature pies (like one with meatballs and giardiniera) and classics (like a soppressata pizza made more interesting with the addition of Calabrian chili honey). It’s a good choice for an easy weeknight dinner.

Alina Tsvor

Split Rail

$$$$ 2500 W Chicago Ave

If you miss going to your friends’ houses for after-school snacks, you’ll enjoy Split Rail in Humboldt Park. The space feels like an old rec room, and the food has the same nostalgic quality. You can get an upscale version of chicken nuggets, and a wild boar bolognese that reminds us of Hamburger Helper (in a great way). Super Mario Bros not included.

Owen & Engine

$$$$ 2700 N Western Ave

This Logan Square spot has an old-school pub feel, with lots of dark wood and leather seats. They do upscale takes on British bar food, so you’ll find dishes like fish and chips, bangers and mash, and a Cornish pasty. There’s also living-room-style seating upstairs, where you can hang out after your meal with a few pints. It’s a good place to have a real meal while also taking in a game on one of the TVs.

Dove's Luncheonette

$$$$ 1545 N Damen Ave

Dove’s, from the same people who own Avec and The Publican, is a diner-style spot serving Tex-Mex food in Wicker Park. The seating is mainly at the counter, on those old-fashioned stools that spin around. Stop here for the pork shoulder, or a brisket taco on a housemade flour tortilla. Sit facing Damen Ave. and get some people-watching in before you head home to your couch.

Cruz Blanca Cervecería & Taqueria

TacosMexican  in  West Loop
$$$$ 904 W Randolph St

Rick Bayless knows you don’t want to cook dinner tonight. Or ferment your own hops. So he does both for you at Cruz Blanca, a West Loop counter-service operation with two levels. The short menu has a few varieties of DIY tacos (all of which come with fresh tortillas and your choice of meat), plus house-brewed beer. Stick with the ground floor for a quick meal, or go upstairs (where there are big tables perfect for groups) if you plan on hanging out for a while.

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