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

12 Chicago Restaurants Perfect For A First Date

Because first impressions matter, and picking the right restaurant is pretty much the most impressive thing you can do.

Written by
11 Spots
Launch Map
11 Spots
Launch Map

First impressions mean a lot, and what restaurant you choose for a first date is pretty much going to make or break your chances of getting lucky, er, married. The Outback probably isn’t the best idea, but neither is Alinea. That means there are a whole lot of choices in between, and it’s up to you to choose wisely. Luckily, you have us here to help.

These are great spots for First/Early in the Game Dates, which is a bit different than Date Night with your long-term significant other. These restaurants offer a perfect balance between good food and good vibes, and are all free of unexpected wild cards that can ruin your night. Ultimately, each is great for getting to know someone over a good meal, and by that we mean getting to know some mostly made up, far more interesting version of the real person you’re having dinner with. Have fun out there.

The Spots

1

La Sirena Clandestina

$$$$ 954 W Fulton Market

The hip, warehouse style room in Fulton Market is the perfect place to grab cocktails and Brazilian inspired food. But you don’t have to worry about the food being too exotic for anyone’s liking. The last thing we want is to put you in an “Along Came Polly” situation.

2

Davanti Enoteca

$$$$
$$$$ 1359 W. Taylor St.

Davanti in Little Italy has exactly the charm you need. It’s ideal for sharing, and everybody likes a sharer. Well, when it comes to food at least. Maybe save the sharing about your weird relationship with your mom for date number two.

3

Maude's Liquor Bar

$$$$
French  in  West Loop
$$$$ 840 W Randolph St

Think intimate French restaurant but in a more modern style. That means trendy atmosphere, great drinks, “almost French” food, and getting a little handsy. The French are always handsy, and realistically we know you’re trying to be too.

4

Lula Cafe

$$$$
$$$$ 2537 N Kedzie Ave

The eclectic Logan Square restaurant has been a staple since opening in 1999, and the neighborhood joint serves every need – first dates included. The dimly lit atmosphere at night has just the right level of romance without trying to take yourself too seriously. Don’t take yourself too seriously.

5

Taxim

$$$$
$$$$ 1558 N Milwaukee Ave

We love this small plates Greek spot in Wicker Park because it gets lively on the weekends. The well-priced Greek wine list will make sure you and your date can get in on the fun too.

6

Pub Royale

$$$$
$$$$ 2049 W Division St

Full-blown dinner date not your thing? Good news, Pub Royale is your spot. Grab a high-top table and ease into things with a cocktail – variations of Pimm’s Cup are their speciality. If it seems like food is in the cards, then the Indian inspired pub food is great for sharing.

7

Riccardo Trattoria

$$$$
$$$$ 2119 N Clark St

Impress the pants off your date with a lively, unpretentious, yet sophisticated Italian restaurant. Figuratively speaking, that is.

8

Parachute

$$$$
AmericanKorean  in  Avondale
$$$$ 3500 N Elston Ave

For those of you who want to prove you know your sh*t when it comes to food, look no further than Parachute. The Avondale restaurant specializes in Korean-American cuisine, but they’re doing it in ways you’ve never seen. Hide your bad qualities with the fact you know where to find a great meal.

9

Vincent

$$$$
$$$$ 1475 W Balmoral Ave

Vincent is intimate without being weird and quiet, nice without being too fancy, and full of a well-to-do crowd without being trendy in a way that says your shallow. Don’t miss out on the mussels menu.

10

Dusek's

$$$$
American  in  Pilsen
$$$$ 1227 W 18th St

Dusek’s is literally a full-service date night. For starters, the food and the atmosphere are both funky, confident, and don’t take things too seriously. On top of that, you have your next move already built in. Head downstairs to Punch House where they make excellent punch-style drinks, or head next door to the attached Tack Room for some traditional cocktails and live piano music.

11

Bar Siena

$$$$
$$$$ 832 W. Randolph St.

Make a move to the first floor bar area at Bar Siena. It shows your’re down with hanging out at places in the West Loop, which you should be, but also that you’re cool with eating basic stuff like pizza and pasta while having drinks. The loud atmosphere sets the tone so you don’t have to worry about awkward silence.

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