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Best Romantic Restaurants in South Side

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481 restaurants available nearby

A photo of Alla Vita restaurant
1. Alla Vita
4.8
Exceptional(2427)
Price: Expensive
• Contemporary Italian • West Loop
Booked 172 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 Roanoke restaurant
2. Roanoke
4.4
Awesome(1531)
Price: Moderate
• American • Downtown / Loop
Booked 84 times today
Roanoke Restaurant, located in the Loop, is a local favorite known for its excellent service and top-tier culinary offerings. The menu highlights artisan comfort food, signature rotisserie dishes, and hand-crafted cocktails. The restaurant's design features luxurious finishes, copper accents, and warm lighting inspired by the rotisserie and brick oven in the open kitchen. Whether you're enjoying happy hour at the bar, dining by the fireplace for a more intimate experience, or joining the vibrant lunch crowd, Roanoke is an ideal spot to gather with colleagues, friends, or family. The restaurant also offers large event spaces that can accommodate up to 250 people.Guests can enjoy parking validation at the 172 W Madison Self-Park Garage. After 4 p.m. on weekends and weeknights, park for free with a $25 meal purchase. Be sure to bring your parking slip for validation. Not valid for valet parking.
A photo of Acanto restaurant
3. Acanto
4.8
Exceptional(3939)
Price: Expensive
• Italian • Downtown / Loop
Booked 61 times today
Across from Millennium park and along Chicago’s Cultural Mile, Acanto Restaurant + Wine Bar is a treasured destination for those who appreciate authentic and approachable Italian food in a conversation-friendly atmosphere. Acanto serves seasonally-driven Italian cuisine from both regions of Italy utilizing artisanal ingredients from Midwest farmers and producers. Acanto boasts one of the most lauded wine programs in the US, including a 3-star rating by World of Fine Wine and a two-glass “Best of Excellence” rating by Wine Spectator. The libations menu is rounded out by Italian classics including spritzes and negronis along with craft cocktails, beer, and spirits. The word Acanto is the Italian translation of Acanthus, the flowery leaf featured prominently in Roman architecture. Famed architect Louis Sullivan used Acanthus in his distinctive terra cotta ornamentation found on the facade of the historically-landmarked building that houses Acanto.
A photo of Proxi restaurant
4. Proxi
4.6
Exceptional(2460)
Price: Expensive
• Contemporary American • West Loop
Booked 24 times today
Proxi offers Modern American Cuisine with cooking that reflects the diversity, innovation, and openness of American culture. Proxi showcases seasonal ingredients in an elegant setting, emphasizing open-fire cooking. Located in Chicago’s West Loop neighborhood along Restaurant Row, Proxi, designed by award-winning Meyer Davis, unites an award-winning team to transport its guests around the world, beginning with cuisine and extending to an eclectic beverage program focused on worldly inspirations and diverse, exotic ingredients. Casual, yet fast-paced service guides Proxi’s international culinary experience, with fine-dining standards and in-depth product knowledge leading the charge, balanced by genuine energy and enthusiasm.
A photo of Bronzeville Winery restaurant
5. Bronzeville Winery
4.4
Awesome(113)
Price: Very Expensive
• Contemporary American • Bronzeville
Booked 31 times today
Bronzeville Winery is a destination where exceptional food, fine wine, and vibrant energy come together. The menu offers seasonal small plates, artisanal cheese boards, seasonal large plates, and a variety of vegan and vegetarian options, ensuring there’s something for every palate. From indulgent Sunday brunch to curated wine and whiskey tasting flights, each visit is a celebration of flavor and creativity. Located just moments away from U Chicago , Hyde Park and 3 minutes from Lake Shore Drive.BW sets the perfect mood with live music every Wednesday and Sunday & DJs for the vibe Thursday - Saturday. Stop by for Happy Hour Wednesdays & Thursdays from 4–6 or gather for unforgettable celebrations, birthdays & dates —whether it’s a party of 30 or a buyout for 200 guests.As the 2023 Jean Banchet Award Winner for Best Hospitality, Bronzeville Winery offers an unmatched combination of warm service, a welcoming atmosphere, and a soulful connection to Chicago’s rich cultural heritage.
A photo of Bar Mar restaurant
6. Bar Mar
4.6
Exceptional(1087)
Price: Expensive
• Spanish • River North (Chicago)
Booked 147 times today
Fresh oysters piled on mounds of sparkling ice. Ceviches that taste of the ocean. Chef José Andrés’ brilliant renditions of iconic seafood classics like fried calamari and lobster rolls. Located at the Bank of America Tower in Chicago, Bar Mar is a true celebration of the bounty of the sea, with modern takes on classics you know and love, festive cocktails, and a bright, beautiful space that interweaves the nautical with the elegant. Beautiful private dining and events spaces available.
A photo of avec West Loop restaurant
7. avec West Loop
4.8
Exceptional(921)
Price: Moderate
• Mediterranean • West Loop
Booked 85 times today
avec, a wine-focused restaurant in Chicago, features Midwestern takes on Mediterranean classics. Inspired by the sun-drenched wine regions of the Mediterranean, avec West Loop has been a Chicago favorite for over 20 years. Originally conceived as a wine bar, avec is the second concept from celebrated one-off hospitality, with communal and bar seating—it is a high-energy, intimate, and interactive experience.For parties of 6 or more, please call us at 312-377-2002.
A photo of El Che Steakhouse & Bar restaurant
8. El Che Steakhouse & Bar
4.7
Exceptional(2186)
Price: Very Expensive
• Steakhouse • West Loop
Booked 73 times today
Located just beyond the West Loop’s famed “restaurant row,” El Che Steakhouse & Bar is Chicago's go-to destination for steak, seafood, and live-fire cooking. The restaurant is modeled after Executive Chef/Partner John Manion’s fascination with Argentinean asados: traditional backyard barbecues surrounding the flame. A 12-foot custom-built grill serves as the centerpiece for this downtown asado which embraces South American-tinged meats, seasonal vegetables, fresh seafood, and of course, steak. The hearth also serves as the heart of the restaurant’s experiences such as dining at the Hearth Table. Join us for happy hour at our cocktail bar, featuring signature cocktails and fiery bar bites or indulge in a glass of wine from the country’s only South American wine list. No matter what you choose, El Che brings the heat seven nights a week.For large groups, private events, birthdays, or celebrations, email us info@elchechicago.com.
A photo of The Gage restaurant
9. The Gage
4.7
Exceptional(12134)
Price: Moderate
• American • Downtown / Loop
Booked 109 times today
The Gage has become a perennial favorite of locals and visitors alike for over ten years by effortlessly blending European influence with American style. The restaurant serves refined, rustic cuisine, innovative libations and an award-winning wine list all in a lively, convivial setting. Known as a “must visit” among Chicago’s dining scene, The Gage continues to evolve by serving well-rounded food and beverage menus that feature classic dishes and drinks with contemporary twists rooted in tradition.
A photo of CH Distillery | Jinsei Motto | Jōtō restaurant
10. CH Distillery | Jinsei Motto | Jōtō
4.9
Exceptional(340)
Price: Very Expensive
• Sushi • West Loop
Booked 35 times today
Starting April 6, all reservations will be for Joto, our incoming sushi concept - book now to be among the first to experience what’s next!CH Distillery | Jinsei Motto in Chicago's West Loop – where expertly distilled spirits meet exquisite sushi. Enjoy our seasonal cocktails and a standout Omakase experience featuring dry-aged fish from Japan. Choose your ambiance: the lively front lounge with a beautifully lit bar and historic distilling tanks, or the serene back dining room with eclectic décor and an Omakase bar. Daily happy hour, whiskey/sake flights, and a patio setting provide diverse experiences. Open for lunch and Sundays, we cater to all occasions. Join us for unmatched culinary excellence and spirited adventures.

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