Whether you’re looking for a full-on spectacle or a cozy and casual night out, the best date restaurants in Chicago have it all.
Impress a first date with knockout Japanese cocktails and bar snacks in the West Loop. Dial up the romance with an elegant Italian meal at a Top Chef’s Gold Coast stunner. Head to Logan Square to dig into exquisite pastas at a MICHELIN-Starred favorites. Whether you’re searching for a casual spot where you can become a regular or a reservation at one of the best Valentine’s Day restaurants in Chicago, these romantic spots have you covered.
Read on for a guide to the 12 top date restaurants in Chicago on OpenTable.
Book a reservation on OpenTable at one of the best date restaurants in Chicago now.
For a first date
For knockout Japanese-inspired cocktails at an intimate cocktail bar – try Kumiko (West Loop)
Julia Momosé’s intimate Japanese-inspired cocktail bar is detail-obsessed, from the hand-carved ice to the delicate glassware. And what it lacks in space, it makes up for in style—elegant accents like geometric patterns in the wood partitions and brass screens have hidden meanings and make for great first-date banter. Toast to a potential second date with Momosé’s next-level cocktails paired with elegant snacks like caviar and Japanese fried chicken. Or extend the evening with the tasting menu.
For a French Riviera-inspired escape at one of Chicago’s most romantic restaurants – head to La Serre (West Loop)
Taking inspiration from the picturesque French Riviera, La Serre screams romance. The lush garden-like setting with greenery hanging overhead and colorful flowers throughout bring the soothing outdoors in even on the coldest Chicago day. Fitting the restaurant’s French vibe, the menu has a dedicated bubbles section, while the wood-burning hearth fires up steaks and mushrooms alike in the open kitchen. Impress your date with caviar service and dover sole meunière for two.
For a second date
For elegant Italian dishes at one of the best date restaurants in Chicago – visit Peanut Park Trattoria (Little Italy/University Village)
Italian gem Peanut Park Trattoria comes from the team behind other inviting local faves like Coalfire Pizza and Tempesta Market, so the warm and rustic vibe is very much on brand. Get better acquainted over linguine vongole, perfectly blistered pizzas, and tender fresh octopus—the restaurant’s tiny but mighty menu earned a nod from The Chicago Tribune’s dining critic just a few months after it opened in 2021. In other words, Peanut Park has second—and third and fourth—dates written all over it.
For knockout pastas in an inviting space – head to Daisies (Logan Square)
After landing in its second home, Italian-by-way-of-the-Midwest Daisies has quickly become a date-night favorite. This MICHELIN Green Star recipient is where you go for exquisite housemade pastas starring seasonal ingredients, many of them sourced from chef Joe Frillman’s brother’s farm outside the city. Don’t miss the lively happy hour, starring creative drinks and tinned seafood.
For an anniversary/romantic milestone
For a swanky seasonal tasting experience from a celebrity chef – reserve a table at Sepia (West Loop)
Sepia has gracefully walked the line between special-occasion restaurant and neighborhood gem since opening in 2007, landing a MICHELIN Star in the process. Its stylish interiors bring out the chandelier-lined space’s past life as a 19th-century print shop—without being precious. The same goes for chef Andrew Zimmerman’s stunning but unfussy contemporary American four-course menu, which features winners like crusted halibut and grilled short rib—making this one of the most romantic restaurants in Chicago.
For stellar Italian cuisine from an acclaimed chef at one of the best date restaurants in Chicago – try Alla Vita (West Loop)
Acclaimed chef Lee Wolen serves a menu that can be dressed up or down at this Italian masterpiece, depending on your celebration mood. If you’re looking to splurge, go for the tuna crudo and wood-fired sea bream. If you’re keeping it casual, get pizza and housemade pasta. Scoring a table at Alla Vita can be trickier than getting a burger at Au Cheval, but you and your date can always grab a spot at the bar. Plan ahead to sit in the dining room with a fabric-covered ceiling and wooden archways.
For a proposal-worthy place
For fine Indian dining at a MICHELIN–Starred restaurant – reserve a table at Indienne (River North)
Kolkata-born chef Sujan Sarkar’s progressive takes on Indian fine dining have earned this River North stunner a MICHELIN Star. With crisp white tablecloths and jewel-toned accents, the sophisticated interiors are as stunning as the restaurant’s artfully plated tasting menus. Up the celebratory vibe with reserve wine pairings.
For sophisticated Italian dining from a Top Chef alum – visit Adalina (Gold Coast/Streeterville)
From the dramatic staircase and glass-enclosed wine room to the cloud-like chandeliers, Adalina is what Chicago date night dreams are made of. Top Chef alum Soo Ahn skillfully whips up refined Italian dishes like charred Sicilian octopus, pillowy gnocchi, and earthy lamb bolognese. Add to the festivities before or after dinner with a visit to Rose Lounge, the restaurant’s intimate first-floor speakeasy.
For a group date
For Korean-inspired riffs on classic steakhouse fare at one of the best date restaurants in Chicago – reserve at PERILLA Steakhouse (Downtown/Loop)
From the blockbuster team behind MICHELIN-recognized Perilla, this classic steakhouse with a Korean twist features an extensive menu of prime meat cuts. Start with shareable plates like crab pancake and foie gras toast before moving on to the main event—premium wagyu prepared tableside on grill tops paired with clever, Korean-inspired cocktails. Enjoy it all in a stunning, AvroKO-designed interior full of light wood, sprawling banquettes, and soft lighting.
For standout American cuisine in a hunting lodge-like setting – head to Frontier (West Town)
If the rustic setting—complete with a roaring fireplace and animal heads on the wall—doesn’t clue you into the adventurous spirit of this charming lodge-like gastropub, perhaps the whole animal experience will. Chef Brian Jupiter slowly smokes wild boar, alligator, lamb, goat, and other meats for group dinners ordered in advance. Hearty sides include garlic rice and mac and cheese. Less pioneer-leaning parties can opt for equally delicious whole salmon and tomahawk ribeye racks.
For an intimate and cozy night out
For a Top Chef champion’s Midwest-meets-Mediterranean hotspot – visit Rose Mary (West Loop)
You’ll find lots of cozy corners for cuddling at this restaurant by Top Chef winner Joe Flamm, from the chef’s counter to under the hanging plants by the wood bar. Flamm’s Midwest-meets-Mediterranean restaurant is a love letter to Adriatic soul food, like burek—a flaky pastry filled with meat and other seasonal ingredients—plus gnocchi with slow-cooked Croatian beef stew. These hearty but unique flavors that lead couples to plan repeat visits to this rustic-chic charmer.
For an evening of eatertainment
For interactive games and crowd-pleasing Italian fare – head to Pinstripes (Gold Coast/Streeterville)
Wood-fired pizzas, seasonal gelato, and handcrafted cocktails—Pinstripes has it all. This modern spin on the old-school bowling alley is the ultimate Chicago eatertainment experience. Gather around the expansive bar to sip craft beer from local breweries and playful cocktails before getting your game on. Either way, everyone goes home a winner at Pinstripes.
From a double MICHELIN-recognized restaurant spotlighting Midwestern ingredients to a casual rustic restaurant where whole animal meals are there for the asking, finding the perfect date night spot for every occasion has never been easier. Don’t miss out on these top date night restaurants. Book with OpenTable now.
Book a table today at one of the best date night restaurants in Chicago on OpenTable.
For more excellent dining options in Chicago, check out these guides:
- 10 top Chicago restaurants for group dining
- 13 swanky restaurants in Chicago for your next celebration
- 12 gorgeous Chicago restaurants that will blow you away
Lisa Shames is a writer focused on travel and food culture in Chicago, IL. She has covered Chicago’s restaurant scene for publications including CS, Chicago Tribune, and Time Out and is the U.S. contributor for Sogoodmag.
Sarah Freeman contributed to this guide.
