12 Chicago Restaurants Guaranteed to Nail Romance on Valentine’s Day

A spread from RPM Italian | Photo Credit: John Stoffer for RPM Italian

There’s perhaps no occasion as important as Valentine’s Day to find the perfect romantic vibe in a restaurant, and when it comes to restaurant romance, Chicago leads the pack. A whopping 12 of the 100 Most Romantic Restaurants in America this year are in the Illinois city, ranging from a chic Italian destination to a Top Chef winner’s small plates wonderland.

Of those 12, six are a part of the legendary Lettuce Entertain You restaurant group, including sceney steakhouse RPM Steak and national seafood favorite Joe’s. Executive partner Jerrod Melman attributes creating a romantic atmosphere to the decor and service.

“We spend a ton of time making sure we have great lighting and that people look good in our spaces,” he says. “We also spend a lot of time on our training so that our teams know when to give people space. No one wants to be a third wheel on a couple’s romantic night out.”

Lighting, service, food, and atmosphere all converge at these 12 spots, resulting in extra intimate vibes. Here’s where to eat this year on Valentine’s Day in Chicago for an ultra-romantic evening.


The deal: Tons of greenery and globe lanterns make this West Loop Mediterranean restaurant from chef CJ Jacobson look like an outdoor oasis any time of year.

The menu: A vast array of Mediterranean and Middle Eastern fare, from multiple types of hummus and spreads to kebabs and cooked meats and seafood populate the menu here. Don’t skip the extensive natural wine selection.


The deal: Critically acclaimed chef Lee Wolen is behind this Michelin-starred Chicago fixture that spawned the well-known Boka Restaurant Group. At this seminal spot in Lincoln Park, find seasonal new American fare paired with a clubby design style that includes a living wall, tons of leather, and exposed brick. 

The menu: A special seven-course menu will be served on Valentine’s Day with dishes such as a foie gras tart; lobster with celery root, daikon, and lobster bisque; and dry-aged strip with turnip, gem lettuce, and salted peppercorn. Dessert from acclaimed pastry chef Meg Galus is a dark chocolate tart with buckwheat, cocoa nib, and passion fruit.

Cafe Ba-Ba-Reeba

The deal: Classic tapas first came to Chicago at this Lincoln Park restaurant from Lettuce Entertain You. The labyrinth-like layout includes a lively bar and plenty of exposed brick.

The menu: All the tapas hits are here: patatas bravas, bacon-wrapped dates, tortilla, garlic shrimp, paella, and more.

A green living wall with tables and chairs beside it

Boka’s dining room | Photo Credit: Boka

Gibsons Italia

The deal: Meat is the focus of this stunning modern Italian steakhouse in River North that has quite the view of Chicago’s famed skyscrapers through wraparound windows.

The menu: Many cuts of steak are the focus of the menu, but plenty of Italian touches make it in, too, with housemade pasta, antipasti like arancini and meatballs, and entrees like veal parmesan.

Girl & the Goat

The deal: Another Boka Group hit, Girl & the Goat is the domain of famed chef Stephanie Izard. She’s been wowing diners in West Loop with her eclectic new American small plates in a high-energy space for nearly a decade. 

The menu: Apple and cheese pierogies, escargot ravioli, duck tartare, and bacon gouda sourdough are just some of the dishes to try.

Joe’s Seafood, Prime Steak & Stone Crab

The deal: The beloved national chain may have started in Miami, but Lettuce Entertain You has made it a Chicago favorite, too. The River North location has soaring ceilings, tuxedoed servers, and tons of dark wood — all of which combine to make it feel like a special occasion, throwback stop.

The menu: All the Joe’s standbys are here, including raw bar, stone crab, fish and seafood, steaks, and eight different potato sides from fried to baked.

Le Colonial

The deal: Bright colors, tropical plants, and white tablecloths fill this Streeterville restaurant that focuses on 1920s French Colonial Southeast Asia and pulls in a solid celebrity crowd.

The menu: Some of Chicago’s best Vietnamese fare can be found here in dishes such as duck noodle soup, fried vegetable rolls, shaking beef, and crispy red snapper with a spicy garlic glaze.

Maple & Ash

The deal: This slightly modernized Gold Coast steakhouse has all the trappings of a classic — stellar martinis, servers in suits, and hunks of high-quality meat — with hipper stylings like velvet chairs and current music. This is an ideal stop for younger couples looking for an updated steakhouse situation.

The menu: Beyond top-notch steak, a wood-fired grill produces all sorts of seafood including lobster and Dover sole, rack of lamb, chicken, and pork chops. Ballers can opt for the $145-per-person “I Don’t Give a F*@k” menu. The extensive wine list has won awards, so be sure to peruse it or ask a sommelier for guidance.

A medium-rare tomahawk steak splayed on a white plate

A tomahawk from RPM Steak | Photo credit: John Stoffer for RPM Steak

RL Restaurant

The deal: That RL stands for Ralph Lauren, who added a restaurant next door to his Chicago flagship store in Streeterville. Classic Americana is on display at this clubby hangout with tons of leather, dark tones, a fireplace, and stiff drinks. THe restaurant predictably pulls in a celebrity crowd.

The menu: Old-school American fare such as shrimp cocktail, pigs in a blanket, lobster bisque, and a burger makes up the menu here.

RPM Italian

The deal: Lettuce Entertain You’s River North destination is also owned by TV-famous Giuliana and Bill Rancic, who created a stylish monochromatic Italian restaurant that has proven to be an enduring hit.

The menu: The menu here is all about sharing dishes from housemade pasta such as prosciutto tortelloni and squid ink spaghetti with crab to red-sauce classics like chicken parmesan and spaghetti and meatballs. There are also tons of appetizers, from warm truffled garlic bread and wagyu carpaccio to fried zucchini and Caesar salad with polenta croutons.

RPM Steak

The deal: Also from Lettuce Entertain You and the Rancics, River North’s modern RPM Steak has similar DNA to RPM Italian, with trendy decor and standout meat.

The menu: Beef lovers will be very happy here, with several types of wagyu, kobe, and cuts to choose from. Raw bar, salads, and sides round out the menu, and while all the steakhouse classics are there, more unexpected choices such as wagyu tataki, blue cheese whipped potatoes, and spicy miso lobster appear, too.

Steak 48

The deal: The famed Mastro’s family brings Chicago this River North steakhouse that has a much lighter aesthetic than a traditional steakhouse, filled with muted greys and modern portraits.

The menu: An in-house butcher operation ages beef right at the restaurant. Inventive starters and sides include deviled eggs with crispy shrimp, tempura asparagus fries, and corn crème brûlée.