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Best Date Night Restaurants in South Side

Discover the best restaurants in South Side

Explore must-try spots, new openings, and hidden gems.

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417 restaurants available nearby

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A photo of Alla Vita restaurant
1. Alla Vita
4.8
Exceptional(2482)
Price: Expensive
• Contemporary Italian • West Loop
Booked 169 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 Virtue restaurant
2. Virtue
4.9
Exceptional(847)
Price: Expensive
• Southern • Hyde Park
Booked 65 times today
Stationed in the Hyde Park neighborhood of Chicago, Virtue is a Southern American restaurant that leads with a culture of hospitality & kindness. We’ve worked hard to create a warm, honest & thoughtful space. We pride ourselves on unpretentious service, timing & most importantly providing great value. At Virtue we use heritage techniques to create some familiar flavors, & some new ones. We hope to see you soon.
A photo of Chemistry restaurant
3. Chemistry
4.5
Awesome(1764)
Price: Expensive
• American • Hyde Park
Booked 115 times today
Located in Chicago's Hyde Park neighborhood, Chemistry is Chicago's premier Black-owned Steakhouse! Enjoy the most delicious steak while experiencing excellent white-glove service. Chemistry exemplifies black excellence at its finest. When the creator of Chemistry first started dating, he wondered "If there were only a place that was breathtaking upon entry, amazing live bands and DJ's, delicious photographable food, good service, along with a place to get up and dance," he’d show up as much as his pockets could afford. However that place didn’t exist, until now. Chemistry, the perfect mix of a high-end late-night steakhouse, booming brunch spot, and tantalizing nightlife vibes all created to be the perfect place to experience love! *Large Parties over 12 are unable to make an online reservation. Please email your request to reservations@chemistrychicago.com Please note: We are not open for dinner service on Friday nights
A photo of Bronzeville Winery restaurant
4. Bronzeville Winery
4.4
Awesome(140)
Price: Very Expensive
• Contemporary American • Bronzeville
Booked 29 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 The Gage restaurant
5. The Gage
4.8
Exceptional(12196)
Price: Moderate
• American • Downtown / Loop
Booked 169 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 El Che Steakhouse & Bar restaurant
6. El Che Steakhouse & Bar
4.7
Exceptional(2213)
Price: Very Expensive
• Steakhouse • West Loop
Booked 78 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 Steakhouse & Bar delivers an authentic taste of Argentina in the heart of Chicago, seven nights a week.For large groups, private events, or celebrations, email us info@elchechicago.com.
A photo of The Alderman restaurant
7. The Alderman
4.9
Exceptional(229)
Price: Moderate
• Cocktail Bar • Pilsen
Booked 10 times today
The Alderman is a cozy, award-winning cocktail bar in Chicago, perfect for a date night. The reviews rave about its intimate, velvet-lined ambiance, and the craft cocktails created by a renowned mixologist. Customers say it's a great spot for private cocktails, date nights, and trying something new. The reviews highlight the exceptional service and unique experience of the bar, making it ideal for a romantic evening.
A photo of Roanoke restaurant
8. Roanoke
4.5
Awesome(1563)
Price: Moderate
• American • Downtown / Loop
Booked 79 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 Cindy's Rooftop restaurant
9. Cindy's Rooftop
4.5
Awesome(46)
Price: Expensive
• Contemporary American • Downtown / Loop
Booked 99 times today
Perched atop the 13th floor of the Chicago Athletic Association hotel under a glass atrium, Cindy's welcomes guests with sweeping views of Millennium Park, the ever-changing blues of Lake Michigan, and beyond. Providing a remarkable backdrop for Top Chef contestant Executive Chef Kaleena Bliss and her inspired menu featuring local wild and seasonal produce and fresh seafood. With vibrant service, an all-season terrace, and an extensive beverage menu that intertwines naturally with the dishes, every detail of your experience is thoughtfully crafted to make a lasting memory. For private events: please reach out to cindysevents@caa.bokagrp.com.
A photo of avec West Loop restaurant
10. avec West Loop
4.8
Exceptional(957)
Price: Moderate
• Mediterranean • West Loop
Booked 86 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.
‘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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