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Best Romantic Restaurants in Old Town

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20 restaurants available nearby

A photo of BLVD Steakhouse restaurant
1. BLVD Steakhouse
4.4
Awesome(2892)
Price: Very Expensive
• Steakhouse • West Loop
Booked 36 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 Rosebud Rosetta Italian restaurant
2. Rosebud Rosetta Italian
4.5
Awesome(2796)
Price: Expensive
• Italian • Downtown / Loop
Booked 17 times today
Rosetta Italian introduces an elegant Italian Restaurant in the heart of the loop, amidst Chicago’s financial district and the finest entertainment venues in the city. Escape the everyday hustle and bustle inside this relaxing dining oasis and enjoy an unforgettable culinary experience. Offering a classic selection of Rosebud's signature Italian dishes, steak, tender chicken entrees, seafood specialties, and a hamburger, voted number one in the city of Chicago by the Chicago Tribune, Rosebud knows a thing or two about the fine art of cooking. Join us for a satisfying lunch before heading back to the office or for a romantic dinner before a show in Chicago’s famed theater district. The inviting atmosphere, impressive wine list and impeccable service at Rosetta Italian encompass the sophistication and style that only Rosetta Italian can deliver. A 3% Surcharge will be added to every check. We will be happy to remove this by request.
A photo of Adalina restaurant
3. Adalina
4.5
Awesome(2310)
Price: Very Expensive
• 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 Eduardo's Enoteca - Gold Coast restaurant
4. Eduardo's Enoteca - Gold Coast
4.6
Exceptional(408)
Price: Moderate
• Italian • Gold Coast / Streeterville
Booked 13 times today
Nestled away in the adorable Gold Coast neighborhood of Chicago, Eduardo’s Enoteca offers authentic Italian fare in an intimate setting, akin to the bistros and cafes of Italy itself. Located at the bustling intersection of Dearborn and Division, Eduardo’s serves as a cozy escape from the busy city streets. This romantic Italian wine bar offers a small-batch boutique wine selection, craft cocktails, handmade pizzas and pastas, charcuterie boards, decadent desserts, and seasonally rotating specials.We ask that each party maintains a 90 minute time limit to accommodate and respect reservations of other guests. Tables will be held for 10 minutes after their reservation time. If you are running late please feel free to call us at (312) 337-4490 to let us know and we will push back your reservation time!
A photo of Bar La Rue restaurant
5. Bar La Rue
4.6
Exceptional(165)
Price: Expensive
• French American • West Loop
Booked 25 times today
Bar La Rue celebrates French-American cuisine with an inventive cocktail program in the heart of Fulton Market. The stylish space boasts a beautiful all-season, street-side, walk-in-friendly pergola bar and dining area, perfect for a cozy patio experience. The menu incorporates French plays on approachable American comfort foods, offering an inviting setting for lunch, brunch, or dinner. Whether you're enjoying cocktails at the bar, celebrating birthdays, or planning a romantic date, Bar La Rue provides a Mediterranean-inspired atmosphere perfect for any occasion.
A photo of Nia restaurant
6. Nia
4.2
Awesome(892)
Price: Expensive
• Tapas / Small Plates • West Loop
Mediterranean inspired menu in the heart of Restaurant Row, conveniently located in the West Loop on Randolph St. Extensive Wine List. Intimate Dining Room and Large Cozy Outdoor Patio at Chicago's most Romantic Restaurant. Notable Wine List & amazing food all made from scratch. Great for Groups. Where food is heart and soul.
A photo of La Serre restaurant
7. La Serre
4.6
Exceptional(412)
Price: Expensive
• French • West Loop
Booked 80 times today
Inspired by the coastal regions of Provence and Saint-Tropez, La Serre, located in Fulton Market, invites guests into a lush and colorful greenhouse setting. The culinary approach highlights the light and vibrant cuisine of Provence, with a focus on native techniques and ingredients, offering lighter takes on the dishes of the French-Mediterranean landscape. Fresh vegetables, seafood, and all-natural Black Angus beef are expertly prepared on the kitchen’s hardwood charcoal hearth, infusing each dish with incredible wood and charcoal flavors, elevating the ingredients without heavy sauces or seasonings.Whether you're enjoying steak, seafood, or Mediterranean-inspired dishes, La Serre is the perfect destination for romantic dinners, dates, birthdays, or fine dining. The bar offers expertly crafted cocktails and drinks, providing the ideal atmosphere for any occasion, from a casual night out to an elegant celebration.
A photo of Michael Jordan's Steakhouse restaurant
8. Michael Jordan's Steakhouse
4.5
Awesome(5364)
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 38 times today
At Michael Jordan's Steak House, we are stewards of legacy rooted in heartfelt hospitality. From the sear on each cut of our Legendary Steak Flight to rolling each piece of our Wagyu Short Rib Truffle Pasta, we strive for the same greatness, spirit and soul that Michael demonstrated on the court. Join us for a romantic date night for a seafood tower garnished with oysters, shrimp and lobster. For a more cozy atmosphere, join us at the bar for a round of our signature cocktails and spirit-free drinks like the Jump Man, Airpresso Martini or Banana Old Fashioned. Break away from a typical brunch with 1-hour bottomless mimosas and Bloody Marys alongside Breakfast Burgers. No greater care is taken with private, fine dining in our historic space as we play a part in crafting unforgettable celebrations— from birthdays to anniversaries and every night in between. Rest assured, our team of all-stars will curate an exceptional group dining experience through our 23-Layer Cake for dessert.
A photo of Fora restaurant
9. Fora
4.4
Awesome(95)
Price: Expensive
• Contemporary American • West Loop
Booked 6 times today
Fora is a premium casual restaurant and outdoor patio serving up a globally inspired menu. Using fresh, high-quality ingredients, our chefs create unforgettable dishes that pay homage to traditional techniques. Our versatile offerings cater to every occasion – from a leisurely weekend brunch to a vibrant weekday lunch, an enticing happy hour from Monday to Friday, to an exquisite dinner service. The essence of our menu lies in its diversity, featuring standout dishes like the refreshingly innovative Brussels Sprout Salad, the comfortingly decadent Smashburger, the boldly flavored Ahi Tuna Tacos, the rustic and satisfying Sausage & Goat Cheese Flatbread, and the classic, perfectly prepared Steak Frites.Enhancing the Fora experience, our guests are treated to live music every weekend. Whether you're gathering for a celebration, a casual catch-up, or a romantic evening, Fora invites you to free your spirit and feed your soul.
A photo of Rosebud Steakhouse - Chicago restaurant
10. Rosebud Steakhouse - Chicago
4.8
Exceptional(3482)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 28 times today
*Rosebud Steakhouse is a special occasion restaurant, with an UPSCALE BUSINESS CASUAL Dress Code Policy. For clarification please review the policy at https://rosebudsteak.com/dress-code/ and we thank you for your courtesy. Welcome to a rare steakhouse, well done! Rosebud Steakhouse knows a thing or two about the fine art of cooking. Located on Walton Street, a stone's throw from Michigan Avenue, this relaxing hideout is the perfect place to enjoy an unforgettable meal paired with a glass of wine from our impressive wine list. The extensive menu features prime steaks by Meats by Linz, fresh seafood and Italian specialties. The beloved hamburger, voted number one in the city of Chicago by the Chicago Tribune, graces our dinner menu. Rosebud Steakhouse invites you to enjoy an unforgettable fine dining experience in a romantic setting. Rosebud Steakhouse is a Creative Hospitality Concepts restaurant. Visit our second location, coming soon to, Munster, Indiana.

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Discover best romantic restaurants in Old Town

Discover the essence of romance in Old Town, Chicago with our curated selection of romantic dining spots. Nestled in this historic and vibrant neighborhood, each restaurant offers a unique ambiance that perfectly sets the stage for an intimate evening. From sophisticated interiors to lively, fun settings, these establishments promise an unforgettable dining experience. Enjoy the convenience of locations that are ideal for a delightful pre-theater dinner or a serene spot to celebrate special occasions. The common thread across these restaurants is their commitment to excellent service, great food, and a truly romantic atmosphere that enhances every meal. Old Town's dining scene is renowned for its eclectic mix of charming eateries that cater to every taste and occasion, making it a prime destination for lovers and food enthusiasts alike. Whether you're planning a date night or a memorable anniversary dinner, you'll find the perfect setting to ignite or rekindle romance in Old Town, Chicago.

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