24 Romantic Restaurants in Chicago That Will Have You Falling Head Over Heels

Best Overall

• Neighborhood: Andersonville
• Yelp Rating: 4 stars
• Specialties: Baked clams, fried calamari, gnocchi gorgonzola
• Price Range: $$

When it comes to romantic restaurants in Chicago, there's none more underrated than Calo Ristorante. As one of the first places my boyfriend took me to, this place left such an impression that it became our official "spot": We've been celebrating special occasions here for more than 13 years now (with plenty of Valentine's Days included). With its warm and inviting candlelit glow, it's plenty cozy, and the sturdy wooden booths are big enough for two to sidle up in side-by-side. The rustic Italian fare is also consistently delicious. (Trust me, after trying just about everything on the menu, I can confidently say you’ll be hard-pressed to have a bad meal here.) The drinks are nothing to sniff at should you need an icebreaker (think Limoncello martinis), and while it does get busy at times, there are very few spots in the restaurant where you’ll feel like another table is sitting on top of you—something that can’t be said for most.

773-271-7782, 5343 N. Clark St., Chicago, IL, 60610; 60640; calorestaurant.com

Most Memorable

• Neighborhood: Lincoln Park
• Yelp Rating: 4 stars
• Specialties: Chocolate and cheese fondue, lobster tail
• Price range: $$$

If it's a memorable evening you seek, it's Geja's Cafe you're going to want to make a beeline for. This longstanding fondue restaurant, which is housed on the lower level of 340 W. Armitage Ave., will instantly transport you to another world with its twinkly lights, classical guitar and flamenco music and semi-private tables with elegant tied-back curtains—and it will be taking things up a notch with V-Day decorations as of February 5. The menu will also leave you more than satisfied, what with its hearty tenderloin and lobster courses and elegant cheese and sensual chocolate dipping sauces, all of which will be incorporated into Geja's three-course Valentine's Day dinner ($100 per person).

773-281-9101, 340 W. Armitage Ave., Chicago, IL, 60614, gejascafe.com

Best Views

• Neighborhood: Gold Coast
• Yelp Rating: 3.5 stars
• Specialties: Braised beef nachos, Italian sausage pizza and vanilla créme brûlée
• Price Range: $$

While the Signature Room on the 95^th floor of 875 North Michigan Avenue (better known to true Chicagoans as the John Hancock Building) tends to get the most hype, the best views in the city can be seen from one floor above at the Signature Lounge. Here, on a clear night, the floor-to-ceiling windows will give you and your significant other an unrivaled panoramic picture of the lakefront. It’s also far more romantic than the restaurant below thanks to its low lighting, cozy round tables à deux and sophisticated shared plates, like Guajillo braised beef nachos and pull-apart French bread. A word to the wise? Avoid popular evenings, like Saturday, when you’ll likely be in waiting in line for a while—the seating is first come, first serve.

312-787-9596, 875 N. Michigan Ave., Chicago, IL, 60610; signatureroom.com

Best Atmosphere

• Neighborhood: Logan Square
• Yelp Rating: 5 stars
• Specialties: Crab cakes, New York strip, shadow shrimp,
• Price Range: $$$

Penumbra isn’t just one of our top picks for one of the most romantic restaurants in Chicago. In 2019, Yelp ranked it one of the most romantic restaurants in all of the nation, due in large part to its dreamy floor-to-ceiling draperies and candlelit tables, which add more than a little ambiance to the scene. It's also set up in just the right manner for you and your hunny to enjoy a private moment (or 12), and the American dishes here get a little Latin love in the kitchen to help spice things up at your table.

773-772-2343, 3309 W. Fullerton Ave., Chicago, IL, 60647; penumbrawinebar.com

Most Sexy

• Neighborhood: Gold Coast
• Yelp Rating: 4 stars
• Specialties: Charred octopus, veal chop parmigiana, campanelle
• Price Range: $$

When you really want to wow your date, head to Adalina: A single glance at the dining room is enough to induce a swoon. Set in the city’s Gold Coast, the interior more than lives up to the neighborhood’s ritzy reputation with its stunning chandelier (this TikTok video of it is basically ASMR fodder), and the menu Italian menu is straight-up droolworthy (we’ll take our fill of chestnut-stuffed cannelloni or salmon vesuvio any night of the week).  Once you’ve finished your meal, you can turn up the heat even further with a visit to the restaurant’s basement sultry Rose Lounge, where you can sip on cocktail specialties like The Centerfold—400 Conejos mezcal, aperol, Genepy del Alpes, citrus, pineapple and a smidge of haberno—to your heart’s content at the ultra-exclusive, secluded corner tables. You also just might spot a star or two—the cast of Vanderpump Rules was filming during my last visit.

312-820-9000, 912 N. State St., Chicago, IL, 60610; adalinachicago.com

Best Wine Selection

• Neighborhood: Gold Coast
• Yelp Rating: 4 stars
• Specialties: Varies by chef
• Price Range: $$$

If it’s a culinary experience you and your hunny are after, the recently re-opened Esquire by Cooper’s Hawk will be a home run. Thanks to the restaurant’s Visiting Chef Series, which brings culinary masters from around the world to its kitchen for extended runs (currently, Top Chef star Brooke Williamson is up to bat), the chances of getting bored with the menu are slim, even if you’ve dined here before. There’s also the Esquire menu, however, for those who tend to latch onto tried-and-true favorites, like the classic tuna tartare, braised shortrib or crispy Yukon potatoes (*raises hand*). Beyond the rotating grub, couples can also head over to the tasting room for a pre- or post-dinner Napa-style wine experience or take a tour of the restaurant’s pièce de résistance: a 50-foot tall glass wine enclosure with a spiral staircase that holds roughly 1,600 bottles of wine from around the world: truly a sight to behold.

312-736-9999, 58 E. Oak St., Chicago, IL, 60611; esquire.coopershawk.com

Most Elegant

• Neighborhood: West Loop
• Yelp Rating: 4 stars
• Specialties: Hamachi crudo, burrata, Spanish octopus
• Price Range: $$$

With nods to Spain, France and Italy (aka the romance countries) infused throughout its DNA, you're bound to fall head over heels for this elegant West Loop pick. Just picture it: You, sipping a cocktail that’s dedicated to the city of lights from one of the space’s plush, velvety stools as the copious chandeliers twinkle overhead at the dignified dark wood bars, reflecting the shimmer in your loved one’s eyes … what were we saying again?

312-680-8217, 838 W. Randolph St., Chicago, IL, 60607; hideandseekchicago.com

Most Intimate

• Neighborhood: West Loop
• Yelp Rating: 4.5 stars
• Specialties: Raw and roasted oysters, cheese spreads, wine pairings
• Price Range: $$

It doesn’t get much more intimate than the quiet, ultra-darkened underground space, complete with a giant candelabra at its center, that is The Press Room. In this 100-year-old building full of Old World charm, you and your paramour can get to know each other over a plate of raw or roasted oysters, a shared cheese spread or the perfect overseas wine selection. Come January 22, the restaurant will also be welcoming a rotating list of local chefs without their own brick-and-mortars to show off their skills for its new Chef Residency program, happening every Sunday evening. First up? Jordan Dominguez of Nomad Sushi. Tickets for the tasting menus are $150 per person.

331-240-1914, 1134 W. Washington Blvd., Lower Level, Chicago, IL, 60607; pressroomchicago

Best Newcomer

• Neighborhood: West Loop
• Yelp Rating: 4.5 stars
• Specialties: Ricotta dumplings, homemade tagliatelle, fennel sausage pizza
• Pricing: $$

The West Loop's recently opened Alla Vita just may be the most romantic newcomer that the Chicago restaurant scene has seen in some time—the floor is hand-painted, for goodness sakes! Despite its high-class surroundings, however, which also include a massive wavy fabric sculpture overhead, tons of greenery and twinkling lights in a wood pergola, the menu is far from pretentious, so you won’t go for broke trying to impress your companion. Instead, you’ll find a whole lot of good old-fashioned homemade Italian comfort food at reasonable prices (a pasta entrée will run you $20 to $28).

312-667-0104, 564 W. Randolph St., Chicago, IL, 60661; allavitachicago.com

Best Location

• Neighborhood: River North
• Yelp Rating: 3.5 stars
• Specialties: Hand-stretched pizzas, Faroe Island salmon
• Price Range: $$

You couldn’t plan a more picturesque meal than one overlooking the Chicago River, and that's just what you'll get when you visit Pizzeria Portofino. Brought to you by the team behind RPM Italian and co., this upscale pizza joint's breezy patio setup is designed to transport you to the Italian Riviera (you can even dock your boat at the nearby Downtown Docks). You can opt for some char-grilled seafood if you're not a fan of hand-stretched pizzas, and once Valentine’s Day weekend gets underway, you’ll also be able to express your love in the form of the heart-shaped pies the eatery will be serving up from February 11 to February 14.

312-900-9018, 317 N. Clark St., Chicago, IL, 60654; pizzeriaportofino.com

Best for a First Date

• Neighborhood: Gold Coast
• Yelp Rating: 4 stars
• Specialties: Shrimp curry, garlic noodles, crispy Brussels sprouts
• Price Range: $$

Dining at Le Colonial is a bit like navigating a choose-your-own adventure novel, since you’ll have your pick of the litter as far as spaces go. While there’s a full dining room with white tablecloths and sexy red booths as well as a bright and airy veranda with greenery galore, we happen to think that you'll be far comfier in the sultry lounge bar at the front, where you and your sweetheart can tuck yourselves into one of the oversized velvet seats and whisper together around the compact-yet-cozy tables. Throw in the best damn garlic noodles I've ever had, and you’ve got all the makings of a great first (or 775^th) date.

312-255-0088, 57 E. Oak St., Chicago, IL, 60611, chicago.lecolonial.com

Most Iconic

• Neighborhood: Loop
• Yelp Rating: 3 stars
• Specialties: Pork ribs, Lockwood burger, Bertha brownie
• Price Range: $$

The Palmer House Hotel may be more than 150 years old, having originally gone up just 13 days before the Great Chicago Fire, but its French-inspired lobby remains one of the most romantic spots in the city to this day. Even more romantic? Sharing a meal and a cocktail at the eatery that overlooks it. While the restaurant is perfectly lovely, it’s the Lockwood Bar, which offers a bird’s-eye view of those stunning ceiling murals from Art Deco painter Louis Pierre Regal and 24-karat gold candelabras by Tiffany & Co., that will really take your outing’s romance factor up a notch. The food is every bit as savory as it is at the sit-down restaurant (you can happily nosh on everything from a burger to pork ribs) and come holiday time, you won’t see a better indoor tree display. We also highly recommend indulging in the Bertha Brownie—the dessert was literally invented here in the 19^th century, and the kitchen still uses the very same recipe.

312-917-3404, 17 E. Monroe St., Chicago, IL; 60603; lockwoodrestaurant.com

Best Food

• Neighborhood: River North
• Yelp Rating: 4 stars
• Specialties: Georges Bank scallops, Wagyu tartare, hand-cut hamachi
• Price Range: $$$

For some, the way to the heart is through the stomach, and if that’s you or your partner, let’s just say you’re in for the most romantic night of your lives at RPM Seafood. The fish dishes here are like nothing you’ve ever tasted in the absolute best way possible (I was basically drooling over the expertly prepared Georges Bank scallops long after I’d devoured them). Come evening time, the mood lighting comes on, making for a super sexy atmosphere, and if you shell out a little extra for the sommelier experience (something I highly recommend), you’ll be treated to two hours of food and wine pairings as poured and explained directly by the restaurant’s master sommelier. (You’ll also get extra-special, VIP seating for you and your hunny.) RPM Seafood also has a special Valentine’s Day wine dinner in the works with 14 different drink selections.

312-900-9035, 317 N. Clark St., Chicago, IL, 60654; rpmrestaurants.com

Most Inviting

• Neighborhood: Gold Coast
• Yelp Rating: 4 stars
• Specialties: Crispy polenta and mushrooms
• Price Range: $$

Every inch of master sommelier and chef Alpana Singh eponymous Gold Coast haunt seemingly beckons to lovers—the wallpaper alone could inspire 1,000 sonnets. With dishes inspired by (what else?) wine, there’s far more to indulge in here together than an appreciation for the decor, however. Both you and your paramour will get a full experience of the palette, exactly as Singh—the youngest woman to ever pass the final level of the Master Sommelier exam—intended (think pinot noir mushrooms and aha tuna crudo meant to transform its flavor according to your grape varietal of choice). Better book those four-course prix-fixe Valentine’s Day dinners ($85) while you still can!

312-624-8055, 831 N. State St., Chicago, IL, 60610; alpanachicago.com

Best Staple

• Neighborhood: Lincoln Park
• Yelp Rating: 4 stars
• Specialties: Corn soup, short rib pie, lamb meatballs, squid ink pasta
• Price Range: $$$

Chances are, if you’ve heard of just one romantic resto on this list, it’s North Pond. While this unique spot in the heart of Lincoln Park was originally built in 1912 as a spot for ice skaters to warm themselves, it’s been a date night staple since 1998, when former chef/partner Bruce Sherman began whipping out “low-country cuisine” with a local and seasonal spin in its kitchen. (The Michelin-starred chef departed North Pond, which is currently helmed by César Murillo, in 2019.) It has since become one of the city’s most adored spots for date night, as it couldn’t be more cozy—only a certain number of people are allowed in each evening—and the quaint pond views and warm fireplace make it just as great of a winter pick as it is in the summer.

773-477-5845, 2610 N. Cannon Dr., Chicago, IL, 60614; northpondrestaurant.com

Best Service

• Neighborhood: River North
• Yelp Rating: 4 stars
• Specialties: Wine pairings,cast-iron mussels, grilled skirt steak
• Price: $$

It’s been said that red wine increases a woman’s sexual desire, but even if you’re a fan of whites, you’ll likely be feeling amorous after a visit to LIVA at the Chicago Winery. Between the cuddle-worthy bar fireplace, the elevated dining room décor (again with those knockout chandeliers) and a menu full of elegant, seasonal bites in the form of Hamachi crudo, cherry blossom-cured duck and umami short rib, there’s more than enough fodder here to get our hearts racing. Better yet? The service just so happens to be tops. A head's up that for Valentine’s Day, the space is offering a special five-course dinner (complete with vino and cocktails) that starts with oysters on the half shell and ends in a delectable duo of ribeye and potato puree with truffled beef jus and chocolate pot de crème. Yum!

312-763-3674, 739 N. Clark St., Chicago, IL, 60654, livachicago.com

Best Hidden Gem

• Neighborhood: Lincoln Square
• Yelp Rating: 4 stars
• Specialties: French onion soup, escargot, Croque madam sandwich
• Price Range: $

Chicago doesn’t end downtown—far from. There’s a whole wealth of neighborhoods to explore and plenty of great romantic spots to be found within them. Case in point? Ravenswood’s Bistro Campagne. Northside couples will love this hidden gem that’s modeled after the bistros of Paris (it is the city of love, after all) and rural France. Small, cozy and charming in its minimalist decor, natural garden touches and low lighting, the restaurant’s menu has a heavy slant toward French cuisine, though regulars will appreciate the fact that it changes seasonally and uses ingredients sourced from local, organic farmers.

773-271-6100, 4158 N. Lincoln Ave., Chicago, IL, 60625; bistrocampagne.com

Best Lighting

• Neighborhood: West Loop
• Yelp Rating: 4.5 stars
• Specialties: Trivoli-cut prime rib, truffle bucatini, whole branzino
• Price Range: $$

Talk about mood lighting! The Hogsalt restaurant group (aka the masterminds behind the similarly impressive Au Chaval, Bavette’s, Ciccio Mio and more) really outdid itself with the launch of Trivoli Tavern in 2020: To dine at this hidden respite with your partner is to escape from the city’s incessant hustle and bustle into. While the room’s enormous hanging cage light is undoubtedly the room’s centerpiece, charming details, like a cobblestone courtyard, soft, yellow glow and plush, leather-style booths, also do their part to draw you in. Foodwise, you can order everything from steak and seafood to handmade pastas, making it a great pick for the couple who can never agree on what to eat.

312-366-2646, 114 N. Green St., Chicago, IL, 60607; trivolitavern.com

Most Authentic

• Neighborhood: The Loop
• Yelp Rating: 4.5 stars
• Specialties: Daily handmade pasta selection, classic tiramisu
• Price Range: $$

Despite the fact that Acanto is centrally located on Michigan Avenue, you won’t be crammed in here like a sardine—the seating is well-spaced and pleasant for conversation (something that’s all-too crucial for cooking up a little romance). There are plenty of sexy shareables (oysters, anyone?), and the food itself is cooked with love: The pastas are handmade daily, the tiramisu offers a modern twist and the wine list is curated with more than 700 selections from 20 regions in Italy.

312-578-0763, 18 S. Michigan Ave., Chicago, IL, 60603; acantochicago.com

Most Nostalgic

• Neighborhood: River North
• Yelp Rating: 4.5 stars
• Specialties: Tuscan cheese bread,baked burrata lasagna, stuffed mushrooms
• Price: $$

There’s a real charm about this Italian gem, which evokes a speakeasy feel with its hanging pendant lights, deep red curtains and nostalgic photos. It’s the perfect spot for getting to know someone over a glass of vino, confessing your deepest, darkest feelings to each other and savoring every last bite of that old-school ravioli. Naturally, Il Porcellino is also taking things up a notch for V-Day with an à la carte menu comprised of prosciutto involtini, lobster tortellini with smoked ricotta and tomato cream sauce, Barolo braised short rib and strawberry cheesecake, all of which will served in-house from February 11 to February 14. (Excuse us while we go make our resos.) Want to celebrate at home? They’ve got a lasagna kit for that ($100).

312-595-0800, 59 W. Hubbard St., 2, Chicago, IL, 60654; ilporcellinochicago.com

Best for Outdoor Dining

• Neighborhood: Financial District
• Yelp Rating: 4 stars
• Specialties: Arroz Chaufa, pan con chicharon slider
• Price Range: $

There’s not a whole lot that’s more romantic than star light gazing … except maybe doing it with your schnookums as you indulge in Peruvian fare that makes your tastebuds dance with delight. Welcome, friends, to Boleo. Nestled into the Kimpton Hotel, this haunt’s retractable glass roof will give a perfect view of the nighttime skyline no matter what time of year it is. Everything, from the vegetarian empanadas to the fried rice, shrimp, mushroom and sweet potato chaufa, is made to share, and the sultry background music will have you in the mood for love, too.

312-750-9007, 122 W. Monore St., Chicago, IL, 60603; boleochicago.com

Most Popular

• Neighborhood: River North
• Yelp Rating: 4.5 stars
• Specialties: Seafood towers, roasted bone marrow, filet mignon
• Price Range: $$$

If Parisian authors like Baudelaire, Proust and Hemingway could have frequented one restaurant in Chicago, it just might be Bavette’s. After all, it’s got plenty of Old Fashioneds to go around, light jazz playing in the background and it’s filled with Chesterton-style sofas and antique-looking furnishings that could’ve been pulled straight from their eras. It’s also always hopping despite its cozy, intimate setup, making it a highly desirable destination for couples who thrive in more social settings. Finally, we’d be remiss not to mention the expertly broiled steaks, crispy fried chicken and roasted bone marrow—this is a Michelin-starred restaurant, after all.

312-624-8154, 218 W. Kinzie St., Chicago, IL, 60654; bavettessteakhouse.com

Most Consistent

• Neighborhood: River North
• Yelp Rating: 4 stars
• Specialties: Dry-aged steakburger, cowboy steak, broiled black cod
• Price Range: $$$$

If you’re more of a steak and potatoes kind of gal (or looking to finger-feed someone who is), there’s always the tried-and-true RPM Steak. As the second RPM restaurant from celebrity business moguls and restauranteurs Bill and Giuliana Rancic, this River North hotspot quickly became just as successful as its Italian predecessor using the same winning formula: one part classy, upscale surroundings, one part damn good food (and plenty of vino besides). In fact, it’s even been called the “golden standard of steakhouses” by one local Yelp reviewer. For those who would rather skip the main course and head straight to uh, dessert (wink, wink), you can order the à la carte menu to-go come V-Day.

312-284-4990, 66 W. Kinzie St., Chicago, IL; 60654; rpmrestaurants.com

Most Cozy

• Neighborhood: River North
• Yelp Rating: 4.5 stars
• Specialties: Truffle mozzarella sticks, Sicilian style swordfish
• Price Range: $$

Last but certainly not least is River North’s Ciccio Mio. Its premise is simple enough—the restaurant’s “about” section of its website merely describes it as a “nice Italian restaurant”—but what it does, it does well, right down to the meatball appetizers. Designed to mimic an Italian supper club, it’s decked out with gilded-frame paintings, miniature table lamps (all the better to canoodle over) and a dark, dramatic color scheme that helps to set the mood. Its limited table offerings, meanwhile, keep things on the über quaint and cozy side—just be sure to make a reservation!

312-796-3316, 226 W. Kinzie St., Chicago, IL, 60654; cicciomio.com