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Best Restaurants for Outdoor Dining in Midway

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74 restaurants available nearby

How are Featured results ranked

A photo of South Side Social restaurant
1. South Side Social
3.7
Very Good(170)
Price: Moderate
• Contemporary American • Oak Lawn
SOUTH SIDE SOCIALNEIGHBORHOOD KITCHEN & TAP South Side Social is where friends come together to relax, watch the game, savor our Chef’s edgy takes on classic South Side dishes, sample locally crafted beers, sip on great wine, and enjoy artfully mixed cocktails in an upscale yet comfortable setting. Serving Breakfast, Lunch, and Dinner.
A photo of Red Lobster - Oak Lawn restaurant
2. Red Lobster - Oak Lawn
3.8
Excellent(42)
Price: Moderate
• Seafood • Oak Lawn
Booked 4 times today
Elevate your day at Red Lobster, where fun meets fancy and every meal is a celebration. Whether you’re marking a special occasion or treating yourself or your crew, Red Lobster is the perfect place to enjoy all your seafood favorites. Dive into our signature shrimp, wild caught lobster and crab, and more. Plus, a variety of fish and popular non-seafood items like our Cajun Chicken Linguini Alfredo. Looking for a showstopper? Create Your Own Ultimate Feast or select a Live Maine Lobster straight from the tank. Or explore our Daily Deals with a different special available each weekday at a price you’ll love. Toast the day with Signature Cocktails including Lobster Punch and Main Deck Margarita Flights to make any moment feel festive. You won’t want to miss our newest menu items or special promotions like Lobsterfest and Crabfest. Reserve online today. Group Dining, To Go, or Catering options. For parties of 11+, please call.
A photo of Pizzeria Portofino restaurant
3. Pizzeria Portofino
4.8
Exceptional(2078)
Price: Expensive
• Italian • River North (Chicago)
Booked 306 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 Cindy's Rooftop restaurant
4. Cindy's Rooftop
4.4
Awesome(140)
Price: Expensive
• Contemporary American • Downtown / Loop
Booked 133 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 Girl & the Goat restaurant
5. Girl & the Goat
4.7
Exceptional(15356)
Price: Moderate
• Contemporary American • West Loop
Booked 212 times today
Girl & the Goat opened in 2010 with the goal of offering a menu of bold, flavorful dishes designed to share in a fun and lively atmosphere. To complement the experience, we offer a curated selection of wines from around the world, focusing on small producers, along with a rotating list of craft beers and a playful cocktail menu crafted by our bartenders. The ever-changing menu, driven by locally sourced and seasonal ingredients, features favorites like sautéed green beans, roasted oysters, crispy short ribs, and confit goat belly. While reservations are encouraged for the dining room, our bar welcomes walk-ins, adventurers, and those who prefer spontaneity.
A photo of Cabra - Chicago restaurant
6. Cabra - Chicago
4.6
Exceptional(3241)
Price: Expensive
• Peruvian • West Loop
Booked 114 times today
Perched atop the Hoxton Hotel in the heart of Chicago’s Fulton Market, Cabra Chicago is a lively rooftop escape, inspired by the bold and vibrant flavors of Peruvian cuisine. Led by James Beard Award and Top Chef winner Stephanie Izard (Girl & the Goat) alongside longtime partners Rob Katz and Kevin Boehm of Boka Restaurant Group, Cabra serves up crave-worthy dishes in a colorful and energetic setting. The restaurant’s airy, plant-filled ambiance, paired with its open kitchen and sweeping city views, creates a dynamic dining experience. Guests can savor a variety of shareable plates, from ceviches to savory meats, all bursting with the rich, fresh flavors of Peru.
A photo of Costera Cocina Tulum restaurant
7. Costera Cocina Tulum
4.5
Awesome(1125)
Price: Moderate
• Mexican • West Loop
Booked 61 times today
Costera Cocina Tulum brings the vibrant flavors of Tulum's coastal and Mayan cuisine to life, blending land-and-sea principles with traditional Mexican dishes. Step into a lively yet serene atmosphere that captures the essence of Tulum's unique intersection of jungle, beach, and bohemian nightlife. Experience our day-to-night philosophy, where "the jungle has two attitudes," and enjoy a dining experience that transports you to this enchanting Mexican getaway.
A photo of River Roast restaurant
8. River Roast
4.4
Awesome(3455)
Price: Expensive
• American • River North (Chicago)
Booked 215 times today
Situated on the iconic Chicago River with stunning views of downtown, River Roast is a lively social house and gathering place. The menu features contemporary American tavern fare with dramatic presentations of whole roasted chicken, whole roasted fish and slow roasted beef; all carved table-side. The food is handcrafted, yet rustic, with many plates designed for sharing. The bar offers a large selection of local beer, craft cocktails, beer, and wine. With one of the best patios in Chicago, River Roast is a great place to enjoy dining outside on a hot summer afternoon or a crisp fall evening. River Roast Private Events offers six spaces, all with spectacular views, for parties from 10 to 1,000. Saturday and Sunday features our Brunch menu from 11:00AM-3PM. We are open Mon-Fri for lunch and daily for dinner.
A photo of Piccolo Sogno restaurant
9. Piccolo Sogno
4.7
Exceptional(7129)
Price: Moderate
• Italian • River West
Booked 151 times today
Our name, which means “little dream” in Italian, was chosen by partners Tony Priolo and Ciro Longobardo because it had always been their dream to open a restaurant of their own. “The restaurant fits our personal goal to get to the heart of Italian wine and food,” says executive chef Priolo. “You go to Italy for simple food prepared by hand with local ingredients. We wanted to bring that experience to Chicago.”Piccolo Sogno features a menu of seasonally fresh rustic Italian cuisine. The impressive all-Italian wine list boasts over 400 selections to pair with your meal.When the weather allows, enjoy al fresco dining in the hidden garden patio-regularly recognized as one of the best in the city.Starting December 1, Monday-Thursday we'll open at 5 pm rather than 4 pm. You are welcome to bring a cake to celebrate. If you do, we will charge a $3 fee per person cake-cutting fee. Beginning January 1, all credit card transactions will be charged a 3% fee.
A photo of Chicago Cut Steakhouse restaurant
10. Chicago Cut Steakhouse
4.7
Exceptional(10190)
Price: Very Expensive
• Steakhouse • River North (Chicago)
Booked 102 times today
Chicago Cut Steakhouse is one of Chicago’s most iconic dining experiences in a city that boasts dozens of options for steak-centric dining. Our downtown Chicago steakhouse offers guests a selection of signature, USDA-certified prime beef that is hand-cut and dry-aged on site. Our curated menu also features fish, shellfish, chops and a selection of unique side dishes and appetizers. In addition to delicious martinis and specialty cocktails, Chicago Cut offers a wine list with more than 600 bottles that has been highlighted Wine Spectator, the world’s leading authority on wine. Our dining area features a lively bar scene, vibrant red velvet banquettes and spacious dining tables, private dining options and beautiful, sweeping views of the Chicago River. In the warm months, we also open our sprawling outdoor dining patio, which makes Chicago Cut an excellent spot for an outdoor brunch, lunch or dinner reservation along the river.

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