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Best Romantic Restaurants in Old Town

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129 restaurants available nearby

A photo of BLVD Steakhouse restaurant
1. BLVD Steakhouse
4.3
Awesome(2915)
Price: Very Expensive
• Steakhouse • West Loop
Booked 82 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(2826)
Price: Expensive
• Italian • Downtown / Loop
Booked 30 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 Geja's Cafe restaurant
3. Geja's Cafe
4.8
Exceptional(5583)
Price: Expensive
• Fondue • Lincoln Park
Booked 60 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 Tre Dita restaurant
4. Tre Dita
4.8
Exceptional(800)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 89 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 Le Colonial - Chicago restaurant
5. Le Colonial - Chicago
4.8
Exceptional(7905)
Price: Very Expensive
• Vietnamese • Gold Coast / Streeterville
Booked 102 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 il Carciofo restaurant
6. il Carciofo
new
4.7
Exceptional(88)
Price: Expensive
• Italian • West Loop
Booked 126 times today
Located in the historic Fulton Market district of Chicago’s West Loop neighborhood, il Carciofo is a Roman Italian restaurant drawing inspiration from the restaurants and markets in one of Chef Joe's favorite cities, Rome. The restaurant offers a seasonal menu of elevated yet familiar Italian fare with traditional antipasti, Roman-style pizzas, hand-rolled pastas produced daily in a dedicated pasta lab and market-driven mains that highlight the season's bounty.
A photo of Boka restaurant
7. Boka
4.8
Exceptional(7173)
Price: Expensive
• Contemporary American • Lincoln Park
Booked 100 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
8. Aba - Chicago
4.8
Exceptional(2654)
Price: Very Expensive
• Mediterranean • West Loop
Booked 321 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
9. Adalina
4.5
Awesome(2360)
Price: Very Expensive
• Italian • Gold Coast / Streeterville
Booked 55 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
10. Alla Vita
4.8
Exceptional(2312)
Price: Expensive
• Contemporary Italian • West Loop
Booked 139 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.

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See what locals rave about

From verified diners like you
From verified diners like you
  • RobVIP
    Chicago / Illinois •14 reviews
    5.0
    Dined today
    My wife and I had an amazing evening. Abby, our server, was incredibly attentive. My wife has a food allergy and Abby knew right away. The few menu items she needed to avoid. The atmosphere is absolutely stunning. All staff members we encountered were so pleasant to engage with. And of course, the food was so wonderful. Abby helped us create a menu in which each item complemented the other. It was just perfect.
    More info
    Tre DitaPrice: Very Expensive• Italian• River North (Chicago)
    •
    4.8
  • Michael
    Detroit / Eastern Michigan •31 reviews
    5.0
    Dined 1 day ago
    My partner and I enjoyed a delicious and unhurried meal here last night. Elsa was our server and she helped to make our entire experience memorable. She carefully explained the evening's specials and answered our questions. We started with the calamari. It was a generous portion and quite tasty. However, the real "gem" was the 8 oz filet. We both ordered one and each one was cooked to perfection. While enjoying coffee at the end of the meal we decided to try the mile high chocolate cake. It was outstanding but be warned: the slice is enough for four or five people! If you are looking for a truly relaxing dining experience, then Rosebud Rosetta Italian is your place to go. Be sure to request Elsa too.
    More info
    Rosebud Rosetta ItalianPrice: Expensive• Italian• Downtown / Loop
    •
    4.5
  • ArturoVIP
    Chicago / Illinois •7 reviews
    5.0
    Dined 2 days ago
    Our dinner for five was wonderful . All the steaks , Fish and sides were cooked to temperature and served accordingly. Teegee our server was great and very attentive. She didn’t rush us and was very helpful with our food selections and recommendations . For us, It was great dining experience.
    More info
    BLVD SteakhousePrice: Very Expensive• Steakhouse• West Loop
    •
    4.3
  • margaret
    Chicago / Illinois •2 reviews
    5.0
    Dined 2 days ago
    Superb Gourmet Vietnamese dishes with a French twist. The ambience is as special and ideally suited to the fare! You’re transported to Old Colonial Vietnam complete with the tropical flavor of banana trees, rotating ceiling fans, a multitude of French lanterns, scattered tribal rugs and old black and white vintage photographs from the French Colonial era. We particularly enjoyed the sea bass and the green curry shrimp. The cocktails were all excellent!
    More info
    Le Colonial - ChicagoPrice: Very Expensive• Vietnamese• Gold Coast / Streeterville
    •
    4.8
  • JodyVIP
    Chicago / Illinois •1 review
    5.0
    Dined 2 days ago
    My experience was really good. The food was amazing. The way the meat would be cooked was interesting. The chocolate fondue was spectacular. Our waiter Tyson was very nice and friendly and he made the experience much better.
    More info
    Geja's CafePrice: Expensive• Fondue• Lincoln Park
    •
    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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