South Side Restaurants
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Summer House - Chicago
Price: Moderate•American•4.7(8,061)Lincoln Park - 2
3 Arts Club Cafe at RH Chicago
Price: Expensive•American•4.8(3,700)Gold Coast / Streeterville - 3
Alla Vita
Price: Expensive•Contemporary Italian•4.8(2,452)West Loop - 4
Rose Mary
Price: Expensive•Croatian•4.8(3,459)West Loop - 5
Gibsons Italia
Price: Expensive•Italian•4.8(4,236)River North (Chicago)
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Tre Dita
Price: Very Expensive•Italian•4.8(1,087)River North (Chicago) - 2
Girl & the Goat
Price: Moderate•Contemporary American•4.7(15,103)West Loop - 3
Cindy's Rooftop
Price: Expensive•Contemporary American•4.6(20)Downtown / Loop - 4
Elina's
Price: Expensive•Italian•4.8(235)West Town - 5
Daisies Chicago
Price: Expensive•American•4.8(361)Logan Square
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Maple & Ash
Price: Expensive•Steakhouse•4.7(4,358)Gold Coast / Streeterville - 2
Sepia
Price: Very Expensive•Contemporary American•4.8(5,431)West Loop - 3
Smith & Wollensky Steakhouse - Chicago
Price: Very Expensive•Steakhouse•4.7(9,287)River North (Chicago) - 4
Chicago Cut Steakhouse
Price: Very Expensive•Steakhouse•4.8(10,112)River North (Chicago) - 5
TAO Asian Bistro - Chicago
Price: Expensive•Asian•4.6(3,309)River North (Chicago)
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- HHeatherChicago / Illinois •2 reviews5.0Dined 1 day agoExcellent service and the food was beyond amazing! Ambiance was perfect.More infoAlla VitaPrice: Expensive• Contemporary Italian• West Loop•4.8
- MMaureenChicago / Illinois •16 reviews5.0Dined 2 days agoAlways delivers top notch quality, service and ambience! I love Virtue! Our server, Alex made our date night experience phenomenal!More infoVirtuePrice: Expensive• Southern• Hyde Park•4.9
- VVERONICAChicago / Illinois •1 review5.0Dined 3 days agoLoved IT!!! Excellent Choice to Celebrate My Birthday. The ambuice of establishment was COZYMore infoBronzeville WineryPrice: Very Expensive• Contemporary American• Bronzeville•4.3
- MMaeveVIPChicago / Illinois •27 reviews5.0Dined 3 days agoWe love the Gage. As, neighbors, we appreciate having a fabulous establishment with great food, people and ambience. The service is the best in the city.More infoThe GagePrice: Moderate• American• Downtown / Loop•4.7
- DDariusChicago / Illinois •1 review5.0Dined 4 days agoService was impeccable and overall a great experience. Definitely will be back soon.More infoChemistryPrice: Expensive• American• Hyde Park•4.4
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Whether you’re looking for a full-on spectacle or a cozy and casual night out, Chicago’s most romantic restaurants have it all. A first-date favorite sweetens the deal with tableside flower carts. Pitchers of hibiscus sangria keep the good times flowing at a Mexican hotspot made for group dates. And if you’re looking to propose, you can’t beat a lavish steakhouse known for the best Chicago River views. This guide pairs Chicago restaurants with romantic occasions from first dates all the way to milestone anniversaries. These are Chicago’s 13 best date-night restaurants.
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Discover South Side
South Side is a neighborhood of Chicago well-know for its centerpiece 319-acre Grant Park, which is home to Buckingham Fountain, one of the world's largest fountains. The South Side is home to many family-owned Polish restaurants, where you can try kielbasa with sauerkraut, kartoflanka with sourdough bread or kotlet mielony with beets and potatoes. There are many sports bars in the neighborhood, which are bustling with activity on weekend nights and weekday evenings when the Chicago Bulls or Chicago Bears are home. The bars feature a full array of stouts, lagers and ales, along with specialty drinks such as bracki Koźlak Dubeltowy from Poland. The South Side is also home to many sub-Saharan-themed restaurants, which offer dishes such as cassava with fava beans.
Frequently asked questions
As of Mar 29, 2025 there are 3 restaurants in South Side. Filter by “outdoor dining”, “romantic” or “dog friendly”.
On OpenTable we support all cuisines. Find American, Mexican and more. Use our filters to find exactly what you’re looking for and make your reservation today.
Yes! We partner with restaurants in South Side who deliver with Toast, Postmates, Uber Eats, Olo, ChowNow.
Yes, you can also see restaurants near you offering takeout.
Yes! OpenTable provides free, convenient and trusted options to book the best restaurants in South Side either on OpenTable or directly with the restaurant.
Yes, we partner with a third party to bring back menu information for restaurants near you.