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Best Romantic Restaurants in Midway, Chicago / Illinois

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79 restaurants available nearby

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A photo of La Serre restaurant
1. La Serre
4.5
Awesome(904)
$$$$
• Mediterranean • West Loop
Booked 66 times today
Inspired by the sun-drenched coastal regions of the Mediterranean, co-founders Luke Stoioff and David Rekhson have assembled a team of acclaimed culinary talent to bring La Serre's menu to life. Leading the kitchen is Chef Nikitas Pyrgis, alongside Chef Partner Athinagoras Kostakos, whose culinary perspective is shaped by his work on iconic Mediterranean concepts such as Noema and Scorpios. Athinagoras is also a Partner in DineAmic Hospitality's LYRA and VIOLI, further anchoring La Serre's menu in a refined yet vibrant Mediterranean ethos.seasonings.
A photo of BLVD Steakhouse restaurant
2. BLVD Steakhouse
4.4
Awesome(3247)
$$$$
• Steakhouse • West Loop
Booked 35 times today
BLVD Steakhouse is a classic American steakhouse inspired by Hollywood's Sunset Blvd—the golden era's famed strip of dining and entertainment establishments. Our space embodies the glamour and luxury that defined Old Hollywood, offering sophisticated yet approachable service with a chef-driven menu of prime cuts, fresh seafood, and other seasonal favorites from Celebrity Chef/Partner Joe Flamm. Outside, our massive full season patio with a sprawling bar evokes an enchanted ‘secret garden’ look and feel with lush greenery, linen curtains, luxe upholstery, and romantic string lighting.
A photo of White Castle - Chicago - W 63Rd St restaurant
3. White Castle - Chicago - W 63Rd St
4.9
Exceptional(9)
$$$$
• American • Midway
Craving fine dining without breaking the bank? This Valentine’s Day, join White Castle for a night to remember! From hot-off-the-grill Sliders to crave-worthy desserts, you’re guaranteed to wow that special someone (or your whole Craver crew) when you book with us. So go ahead—slide into those DMs and, if the vibe is right when the night wraps up, maybe even “put a ring on it.” A Chicken Ring, of course. Give the special Cravers in your life the royal treatment at White Castle on February 14th. Because everyone wants to hear those three little words: We’re. Getting. Sliders.
A photo of Adalina Italian restaurant
4. Adalina Italian
4.7
Exceptional(2919)
$$$$
• Italian • Gold Coast / Streeterville
Booked 68 times today
Adalina in Chicago is a perfect place for a romantic evening. The reviews highlight its beautiful, elegant, and dimly lit setting that's perfect for a date night. The restaurant's ambiance, excellent service, and beautiful decor create a romantic atmosphere. The Michelin-starred chef Soo Ahn's modern and engaging Italian menu is also a hit with the customers.
A photo of RPM Seafood restaurant
5. RPM Seafood
4.7
Exceptional(2749)
$$$$
• Seafood • River North (Chicago)
Booked 201 times today
Introducing RPM Seafood, a dramatic multi-level restaurant overlooking the iconic Chicago River featuring the truest expression of the world’s best fish and seafood.The sister restaurant to RPM Steak and RPM Italian, it marks the third collaboration between partners RJ, Jerrod and Molly Melman of Lettuce Entertain You Enterprises and celebrity couple Giuliana & Bill Rancic.
A photo of Miru at The St. Regis Chicago restaurant
6. Miru at The St. Regis Chicago
4.7
Exceptional(2069)
$$$$
• Japanese • River North (Chicago)
Booked 105 times today
Miru, Japanese for "view" celebrates the flavors and cuisine of Japan.  We invite you to join us for a collection of sharable dishes including tempura and crispy rice, a robust seafood and beef selection, as well as expertly crafted sushi, overlooking the Chicago River and Navy Pier.
A photo of Le Colonial - Chicago restaurant
7. Le Colonial - Chicago
4.9
Exceptional(8458)
$$$$
• Vietnamese • Gold Coast / Streeterville
Booked 89 times today
Le Colonial is a celebration of seductive spirit and vivid flavors reminiscent of Saigon in the 1920s. With locations in Atlanta, Denver, Delray Beach, Houston, Lake Forest, and Naples, the famed Vietnamese restaurant is designed to capture a bygone era of sophistication and opulence. Celebrated restaurateurs Rick Wahlstedt and Joe King deliver exquisite attention to detail in the luxurious, classic, and romantic atmosphere perched on Oak Street in Chicago’s Gold Coast. For special occasions, our private dining space provides a bespoke setting for unforgettable celebrations.
A photo of Trino restaurant
8. Trino
4.7
Exceptional(145)
$$$$
• Steakhouse • West Loop
Booked 34 times today
2025 EATER AWARDS BEST NEW RESTAURANT: "In an era when Chicago’s already robust steakhouse scene is booming, it’s easy to mistake Trino for just another carbon copy. The steakhouse classics are unquestionably impressive: Sweet Sinaloa blue shrimp blossoms with a dip in the rojo cocktail sauce while beef tartare mixes tallow aioli, mustard, machaca, and a cured yolk for surprising depth. It’s when you stray from the expected, though, that Trino reveals its true character. From the verdant cangrejo tostada of crab, avocado, dill, Asian pear, and pistachio to the buttery empanadas stuffed with spiced lamb... beef picanha, the prized Brazilian cut, is seared on a Vulcan plancha that mimics the heat of an Argentinian chapa, and paired with sauces like corn liqueur au poivre and pequin pepper chimichurri. It’s a break from tradition and a deeply personal project for Chef Stephen Sandoval — with 'Trino' his Grandfather's name - and exactly the kind of steakhouse Chicago needs right now."
A photo of Vela restaurant
9. Vela
4.5
Awesome(304)
$$$$
• Mexican • River North (Chicago)
Booked 15 times today
Vela Bar y Cocina, located in the heart of River North, Chicago, brings the vibrant flavors of Mexico City to life. Our menu showcases authentic Mexican cuisine with a modern twist, from flavorful tacos to traditional dishes. Sip on expertly curated cocktails featuring a vast selection of tequila and mezcal, including rare pours. Vela offers the perfect venue for private dining and events, with intimate spaces like our Private Dining Room and the stylish Zona Rosa. Whether you're enjoying a casual night out or hosting a private event, Vela delivers a warm and cosmopolitan experience infused with Mexican spirit. Join us for an unforgettable evening of food, drinks, and culture in one of Chicago's most energetic neighborhoods.Vela Late Nights! Every Friday & Saturday, 10:30pm-1am. Live DJ's. Choose one of our experiences or reach out at afterdark@velabarcocina.com to get on the guestlist.
A photo of NoMI restaurant
10. NoMI
4.6
Exceptional(3261)
$$$$
• Sushi • Gold Coast / Streeterville
Booked 45 times today
NoMI, perched above North Michigan Avenue at Park Hyatt Chicago, offers sweeping views of the Water Tower and Lake Michigan. Each “experience” represents a distinct seating area within the venue, NoMI Kitchen, NoMI Lounge, or NoMI Garden, allowing guests to select their preferred setting.NoMI Kitchen features a menu rooted in Midwestern influences, with steaks, housemade pastas, and inventive seasonal dishes. Weekend brunch includes both classic and seasonal favorites.NoMI Lounge offers a full sushi bar, shareable bites, creative cocktails, and an extensive wine list.NoMI Garden, the seasonal outdoor terrace, provides open-air dining with city views and a menu of light fare.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

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