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Best Restaurants for Outdoor Dining in South Side

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81 restaurants available nearby

A photo of Il Culaccino restaurant
4.3
Awesome(1092)
Price: Moderate
• Italian • South Loop
Booked 9 times today
If your preferred time is unavailable please call for possible openings. Il Culaccino, the new fine Italian dining restaurant presented by the Franco’s Restaurant Group, comes to McCormick Square in Spring 2019. Anchored in the Arrive Lex Apartment Tower, 2134 South Indiana, Il Culaccino is just steps away from Wintrust Arena and a short walk from McCormick Place. At Il Culaccino, you’ll enjoy unique wines and delicious plates accompanied by the friendly and superior service that has become the hallmark of Franco’s Restaurant Group, family-owned since 1989.Be prepared to have your senses thrilled at Il Culaccino, before or after exploring McCormick Square, Chicago’s most exciting and vibrant new entertainment district.
A photo of Acanto restaurant
4.8
Exceptional(3917)
Price: Expensive
• Italian • Downtown / Loop
Booked 27 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 Remington's restaurant
4.6
Exceptional(3301)
Price: Moderate
• American • Downtown / Loop
Booked 35 times today
Turn to Remington's to create a memorable experience for your upcoming event! Our venue can accommodate your group of 10 to 225 guests for breakfast, lunch, dinner, or a cocktail reception in a variety of private and semi-private dining spaces. Whether you're having an intimate gathering or a large corporate meeting, our sleek restaurant is the perfect spot to host your VIP guests in the heart of Chicago's Millennium Park area.
A photo of Bandol restaurant
4.1
Excellent(276)
Price: Moderate
• Contemporary French / American • Downtown / Loop
Booked 6 times today
Bandol blends French and Mediterranean classics with modern seafood, a raw bar, and American influences, inspired by the coastal town of Bandol. Its light-filled, art-deco space is ideal for everything from a morning espresso and pastry to a business lunch, memorable dinner, or late-night digestif. Parisian-style outdoor seating offers a relaxing escape in the heart of the city. Bandol serves breakfast, lunch, dinner, weekday happy hour, and weekend brunch.The upscale to-go coffee bar and bakery counter offers Lavazza coffee, grab-and-go breakfast items, and house-made pastries, perfect for a quick pick-me-up.Parking validation is available for guests parked at 172 W Madison Self-Park Garage. After 4 p.m. on weekends and weeknights, enjoy free parking with a $25 meal purchase. Bring your parking slip for validation. Not valid for valet parking.
A photo of Tapas Valencia restaurant
4.7
Exceptional(2483)
Price: Moderate
• Tapas / Small Plates • South Loop
Booked 10 times today
Located in Chicago’s South loop, we offer creative Spanish tapas, unique cocktails, and a lively atmosphere with walls adorned in multi-colored mosaic artwork reminiscent of the art of the great Spanish artists Joan Miro and Antoni Gaudí! Whether you’re dining with friends and family, exploring on a first date, or planning your next big event, Tapas Valencia is the perfect backdrop for any occasion. We carry on the tradition of great food and service that was started at our original location, Mesón Sabika in Naperville.
A photo of Tuscany on Taylor restaurant
4.8
Exceptional(2231)
Price: Moderate
• Italian • Little Italy / University Village
Booked 9 times today
Tuscany on Taylor is the original Tuscany restaurant opened in 1990 in the heart of Little Italy. A comfortable trattoria, Tuscany serves Northern Italian favorites including: homemade pastas, pizzas from our wood-burning ovens, signature Italian chicken dishes, grilled veal and other authentic dishes. Private party space available.
A photo of Chez Joel restaurant
4.9
Exceptional(2683)
Price: Moderate
• French • Little Italy / University Village
Booked 8 times today
In the midst of Little Italy, Chez Joel creates the tastes and aromas of France for. Featuring traditional favorites, Chef Joel Kazouini offers his straightforward, expertly prepared Southern French cuisine. Chez Joel’s atmosphere is reminiscent of a true French bistro; its walls adorned with French posters and tables covered with butcher paper. The cozy environment makes Chez Joel the perfect spot for any romantic meal, and when weather permits, garden tables offer an open-air experience where you’ll find one of the most divine al fresco dining settings in the city. Chez Joel Since 1999
A photo of FireLake Grill House and Cocktail Bar restaurant
4.2
Awesome(14)
Price: Expensive
• American • Downtown / Loop
Booked 5 times today
Experience farm-to-table dining in the heart of Downtown Chicago at FireLake Grill House & Cocktail Bar. The acclaimed American grill concept, known for its wood-fired cooking, offers a menu featuring the Midwest's best meat, freshwater fish and produce. Steps from Lake Michigan and Millennium Park, FireLake is an inviting showcase for the excellent food and welcoming spirit that define our city.
A photo of Pizzeria Portofino restaurant
4.8
Exceptional(1679)
Price: Expensive
• Italian • River North (Chicago)
Booked 201 times today
Pizzeria Portofino is a sun-drenched casual restaurant located directly on the Chicago riverfront offering hand-stretched pizzas, coastal wines, an expansive patio and breezy decor that will instantly transport you to the Italian Riviera.
A photo of Gibsons Italia restaurant
4.8
Exceptional(4140)
Price: Expensive
• Italian • River North (Chicago)
Booked 137 times today
Gibsons Italia is built on a tradition & elegance that is relentless in the pursuit of the very best. Chef-driven tastes of Italy are paired with the superiority of Gibsons Steakhouse, creating a restaurant that makes the familiar, exceptional. Beautiful private dining and events spaces available.

See what locals rave about

From verified diners like you
From verified diners like you
  • Florentino
    Chicago / Illinois •1 review
    5.0
    Dined 1 day ago
    We had a wonderful time at this restaurant. From the moment we arrived, the service was fantastic. Our drinks and food were served promptly, and everything we ordered was delicious. The sangria was a particular highlight, as were the other drinks we tried. We were so pleased with our first visit and are already planning our next one.
    More info
    Tapas ValenciaPrice: Moderate• Tapas / Small Plates• South Loop
    4.7
  • Jeff
    Chicago / Illinois •2 reviews
    5.0
    Dined 1 day ago
    We had an absolutely wonderful evening at Acanto! The ambiance, service, food and wine were all excellent! I proposed to my (now) fiancée and they went above and beyond to ensure that we had a perfect romantic experience. Thank you Patti, Cassandra, and the rest of the staff for your help making this a great memory we will always have!
    More info
    AcantoPrice: Expensive• Italian• Downtown / Loop
    4.8
  • KededraVIP
    Chicago / Illinois •4 reviews
    5.0
    Dined 2 days ago
    The team was amazing from the host to the server to the bartender. Food was great perfectly prepared perfectly and timely. Shouts our to Brandon our server who showed us great service even though we were his last table definitely will be back in the future and to Destiny the host i appreciate you so much for allowing us to still be seated the team was amazing.
    More info
    BandolPrice: Moderate• Contemporary French / American• Downtown / Loop
    4.1
  • Kimberly
    Chicago / Illinois •163 reviews
    5.0
    Dined 5 days ago
    Everything about lunch at Remingtons was perfect. The decor is very sophisticated and pleasant. Service couldn’t be any better. And the food is very good classic American. My only complaint is their prices. They are exceedingly high. An appetizer crab cake, while quite delicious, is $22. In addition, they charge 3.5% sur charge. This just seems excessive.
    More info
    Remington'sPrice: Moderate• American• Downtown / Loop
    4.6
  • Victor
    Chicago / Illinois •1 review
    5.0
    Dined on Jan 19, 2025
    Service was good and the food was delicious, but like every Italian restaurant these days, the prices are higher
    More info
    Il CulaccinoPrice: Moderate• Italian• South Loop
    4.3
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