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Best Romantic Restaurants in Old Town

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130 restaurants available nearby

A photo of BLVD Steakhouse restaurant
1. BLVD Steakhouse
4.4
Awesome(2911)
Price: Very Expensive
• Steakhouse • West Loop
Booked 50 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(2822)
Price: Expensive
• Italian • Downtown / Loop
Booked 32 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 Tre Dita restaurant
3. Tre Dita
4.8
Exceptional(776)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 154 times today
Led by Chef Evan Funke, Tre Dita, Italian for "three fingers", pays homage to the precise measurement of bistecca Fiorentina. If booking in the dining room at Tre Dita, you will enjoy a menu of antipasti, handmade pastas, signature entrees and steaks. If booking in the Bar Tre Dita, you will enjoy a smaller menu of stuzzi, antipasti, handmade pastas and entrees. The full cocktail, wine list and dessert menu is available in both locations.Please note that Tre Dita only accepts reservations 7 days in advance.
A photo of Geja's Cafe restaurant
4. Geja's Cafe
4.8
Exceptional(5573)
Price: Expensive
• Fondue • Lincoln Park
Booked 42 times today
For over 59 years, fondue dining at Geja’s Café has been a favorite indulgence for Chicagoans as well as out-of-towners. It’s a perfect way to kindle romance, celebrate a special occasion or simply join family and friends for a fun and unforgettable dining experience.To start we offer a Swiss Gruyere cheese fondue, served with fresh breads, fruits and vegetables for dipping. Our crisp house salad, dressed with tangy Dijon vinaigrette, offers a counterpoint to the rich, warm cheese fondue appetizer.Next, you’ll cook your choices of Australian lobster tail, Gulf shrimp, beef tenderloin, fresh sea scallops or boneless chicken breast in a pot of sizzling soybean oil or broth. The main course is served with fresh vegetables and eight gourmet dipping sauces.Our famous chocolate fondue is flamed table-side, and presented with marshmallows for roasting and other delectable dippers.A 4 % operational fee is added to all checks to work in concert with Chicago's One Fair Wage Ordinance.
A photo of Le Colonial - Chicago restaurant
5. Le Colonial - Chicago
4.8
Exceptional(7888)
Price: Very Expensive
• Vietnamese • Gold Coast / Streeterville
Booked 81 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 Boka restaurant
6. Boka
4.8
Exceptional(7171)
Price: Expensive
• Contemporary American • Lincoln Park
Booked 77 times today
Michelin-starred Boka Restaurant has been a cornerstone of Chicago’s dining scene since 2003. In 2014, following a major renovation, Chef Lee Wolen joined as Executive Chef and Partner, quickly gaining critical acclaim. Named “Chef of the Year” by both Phil Vettel of the Chicago Tribune and Eater Chicago in 2014, and again in 2015, Lee has helped elevate Boka to new heights. The restaurant offers contemporary American cuisine that highlights seasonal ingredients sourced from local farms. The sophisticated yet inviting ambiance sets the stage for an exceptional dining experience, with daily-changing tasting menus that showcase timeless and seasonal American flavors.
A photo of Aba - Chicago restaurant
7. Aba - Chicago
4.8
Exceptional(2635)
Price: Very Expensive
• Mediterranean • West Loop
Booked 217 times today
Aba is a Mediterranean restaurant with locations in Chicago, IL, Austin, TX, and BalHarbour, FL. Aba, meaning father in Hebrew, incorporates Chef CJ Jacobson’s lighter styleof cooking with influences from the Mediterranean, including Israel, Lebanon, Turkey, andGreece. The bar program showcases rare Mediterranean-inspired wines and spirits.Signature dishes include Smoky Garlic Hummus, Muhammara, Heirloom Crispy ChickenThigh, Shawarma-Spiced Skirt Steak, Grilled Salmon Kebab and more. The bar programshowcases rare Mediterranean-inspired wines and spirits.
A photo of Adalina restaurant
8. Adalina
4.5
Awesome(2347)
Price: Very Expensive
• Italian • Gold Coast / Streeterville
Booked 52 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 Alla Vita restaurant
9. Alla Vita
4.8
Exceptional(2300)
Price: Expensive
• Contemporary Italian • West Loop
Booked 136 times today
Serving a casual, family-style menu, Alla Vita is a place to gather and enjoy comfortable Italian cuisine. Alla Vita means “to life” in Italian which recognizes overcoming life's challenges and creating a space for shared meals and memorable experiences. Executive Chef Lee Wolen shares his passion for fresh, delicious Italian food made simply with the best ingredients. Follow @allavitachicago to stay up-to-date with the latest happenings.
A photo of Nonnina restaurant
10. Nonnina
4.6
Exceptional(2855)
Price: Moderate
• Italian • River North (Chicago)
Booked 70 times today
Nonnina is a romantic spot in Chicago, offering old-school Italian cooking with a retro vibe. Reviews frequently mention the 'cute', 'comfortable', and 'intimate' ambiance, perfect for a date night. One review mentioned a 'romantic dinner for 2' on their anniversary, with 'excellent service'. Another highlighted a 'beautiful red velvet booth' for a 'date night'. The combination of great food, exceptional service, and a cozy atmosphere makes Nonnina an ideal place for a romantic evening.

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See what locals rave about

From verified diners like you
From verified diners like you
  • Allison
    Chicago / Illinois •2 reviews
    5.0
    Dined 1 day ago
    Wonderful food, wonderful service, wonderful environment. Would definitely recommend.
    More info
    Rosebud Rosetta ItalianPrice: Expensive• Italian• Downtown / Loop
    •
    4.5
  • CourtneyVIP
    Chicago / Illinois •4 reviews
    5.0
    Dined 2 days ago
    My favorite restaurant in all of Chicago. Consistently fantastic. The crispy veggie egg rolls, chicken dumplings, signature fried rice, and shaking beef are musts. The cocktail program could use some TLC but the food is so good it doesn’t matter.
    More info
    Le Colonial - ChicagoPrice: Very Expensive• Vietnamese• Gold Coast / Streeterville
    •
    4.8
  • Erin
    Chicago / Illinois •1 review
    5.0
    Dined 4 days ago
    This is the best restaurant I have ever been to in my 31 years of continued existence. The staff is so kind and they remember myself and my partner every time we come in because we come in once a month. The cheese is delectable, the main course is utterly mouthwatering, and don’t even get me started on the chocolate. 100000/10 can’t wait to come again.
    More info
    Geja's CafePrice: Expensive• Fondue• Lincoln Park
    •
    4.8
  • Qui
    Chicago / Illinois •1 review
    5.0
    Dined 6 days ago
    This place was very beautiful. Enjoy my experience. The food was good. Service was great. Only thing I didn’t care for was the music for such a beautiful elegant place they wasn’t playing Christmas music that wasn’t playing jazz music or instrumental music they were playing techno music I did not care for that in such a beautiful setting. The music should’ve been jazz , Christmas,something soft playing not techno music that really threw me off in such a beautiful setting
    More info
    BLVD SteakhousePrice: Very Expensive• Steakhouse• West Loop
    •
    4.4
  • MAry Ann
    Chicago / Illinois •6 reviews
    5.0
    Dined on 16 Dec 2024
    Dining at Tre Dita was an exceptional experience from the time we were greeted at the hostess stand to the time we left. The timing of the service of each course was perfect! We never felt rushed and we did take our time enjoying each and every bite! All staff were great. Our server Nina was exceptional! Great knowledge of the dishes as well as the wines that complimented them. She was so genuine, nice and fun which added so much to our experience! We had the squash blossoms, blue prawns, insulate di cicoria (which was plentiful- we shared it) wild boar papperdelle pasta dish, and spaghetti ala vongole! Had a great bottle of vermentino that was featured this week. Finished with tiramisu, espresso martini and limoncello! Buonissima! Almost forgot to mention the view! Gorgeous!
    More info
    Tre DitaPrice: Very Expensive• Italian• River North (Chicago)
    •
    4.8

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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