10 Chicago Restaurants That Will Impress Your Girlfriend

If you had it your way, you’d probably spring for the “Pick 2 for $2” special at TGI Fridays on date night. But, when it comes to maintaining a relationship, the mall food court is the first step towards making a shameful return to Tinder. If you’re in this thing for the long haul, then it’s important to, like, show effort and stuff. With that in mind, here is a list of sophisticated, v. lux restaurants in the Windy City that will make you look like a refined gentleman, even though we both know the truth. Dig in with these 10 Chicago Restaurants That Will Impress Your Girlfriend. You’re welcome in advance.

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Neighborhood: Near North Side
Address: 330 N. Wabash Ave.
Website: travellechicago.com

You know when you and your girl are watching Access Hollywood and Billy Bush starts squawking about how Ashton Kutcher took Mila Kunis to a vacation in the South of France? And then, your girl looks at you the way Justin Bieber looks at a prosecuting attorney? And then, you look at yourself in tapered sweatpants and—at that exact moment—totally understand her frustration? Well, Travelle—located on the second floor of The Langham—offers Mediterranean cuisine, a 1,600-bottle wine list and a pretty spectacular view of the Chicago River. While it’s not a yacht off the coast of Monaco, it is a one-way ticket out of the doghouse.

Neighborhood: Lincoln Park
Address: 2610 N. Cannon Dr.
Website: northpondrestaurant.com

North Pond, as the name implies, is set along a small body of water in Lincoln Park. Look at this picture; the place practically invites you to fall in love all over again. Like many restaurants on this list, North Pond has the potential to roundhouse kick your credit balance in the face, but the occasional tasting menu with add-on wine pairing is what being a responsible boyfriend is all about.

Neighborhood: Near North Side
Address: 111 W. Hubbard St.
Website: celestechicago.com

Celeste, a multi-level lounge/restaurant concept that opened last month, offers a 40 page cocktail menu and cuisine that, as you might expect, pairs well with the extensive drink choices. This place is open late. So, if you and bae are buried with unwatched episodes of Shark Tank, then your Friday is still salvageable after the TiVo binge. We recommend the cornflake crusted fried chicken with cherry bomb hot sauce, which is available some nights, in limited quantities. The best stuff is always available “some nights, in limited quantities.”

Neighborhood: Near North Side
Address: 52 W Illinois St
Website: rpmitalian.com

RPM is an Italian restaurant, but it’s located in River North and partially owned by a chick from the E! Network; so don’t expect checkerboard tablecloths and walk-in seating. The spot is buzzing, busy, and crawling with conventionally attractive people who know their way around a bottle service menu. Yes, junior high is finally over. You can sit with the cool kids now. Don’t forget to order the chocolate bowl with salted caramel for dessert, because that thing is absurdly delicious.

Neighborhood: Near North Side
Address: 720 N. Wells St.
Website: boardinghousechicago.com

You can tell by this chandelier, which features more than 9,000 wine glasses, that this night is going to be a winner. And, the tribute to fermented grape juice that greets you at The Boarding House isn’t just for show. Alpana Singh, the youngest woman ever to pass the master sommelier exam, opened the five-story space in 2012. In other words, this place takes wine as seriously as you take X-Box Live, only your girl won’t cringe when she’s exposed to this kind of zealotry.

Neighborhood: Lincoln Park
Address: 1816 N. Clark St.
Website:jparkerchicago.com

Chicago’s currently in the throes of an ice age, so al fresco dining might seem like another year away. But, the drunken Cubs fans wandering Clark Street remind us that summer is just around the corner. Located atop Hotel Lincoln, J. Parker comes equipped with an incredible aerial view of Lincoln Park and a menu that’s a step above your orthodox collection of bar bites. This is a drinking spot first, but still delivers a great meal.

Neighborhood: West Loop
Address: 564 W. Randolph St.
Website: embeya.com

Embeya is a palatial, visually stunning addition to the West Loop’s already distinguished assortment of restaurants, and it’s so ridiculously opulent that you might be able to convince your girl that it’s “invite only.” Besides landing on Esquire's "Best New Restarurants of 2013” list, Embeya was recognized with two Jean Banchet Awards in 2014, including Best Restaurant Design and Rising Chef (Thai Deng).

Neighborhood: Near North Side
Address: 868 N. Franklin St.
Website: mkchicago.com

What was once a factory in the 1920s is now Chef Michael Kornick’s ode to the impeccable date night. mk has a flawless setting, but there’s nothing contrived about the environment. This place, with its tableside visits from the chef, has just plain kicked ass for over a decade and a half. mk has a long and exalted history when it comes to strengthening bonds, and you can’t go wrong with the classics.

Neighborhood: West Town
Address: 730 W Grand Ave
Website: the-dawson.com

The Dawson’s interior is as an exposed steel and brick marvel, which gives your on-scene Instagram pictures triple digit “like” potential. Bottom line, this place looks important. And, with multiple levels and more than 12,000 square feet of space, you’ll feel like you’re a part of something bigger and more energetic than dinner. We could all use a little more excitement in our lives.

Neighborhood: Near North Side
Address: 401 N. Wabash Ave.
Website: sixteenchicago.com

Located on the 16th floor of the Trump International Hotel & Tower, Sixteen (get it?) sits on the Chicago River and is positioned alongside the Wrigley Building’s Clock Tower. So, this place could serve Hot Pockets and unsweetened iced tea and still provide a worthwhile dining experience. Thankfully though, the cuisine—as prepared by Executive Chef Thomas Lents—has been recognized with a two-star rating in the 2014 Michelin Guide, as well as four-star reviews from both the Chicago Tribune and Chicago Magazine.