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Best Restaurants for Outdoor Dining in Midway, Chicago / Illinois

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50 restaurants available nearby

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A photo of Piccolo Sogno restaurant
1. Piccolo Sogno
4.8
Exceptional(7329)
$$$$
• Italian • River West
Booked 120 times today
Our name, which means “little dream” in Italian, was chosen by partners Tony Priolo and Ciro Longobardo because it had always been their dream to open a restaurant of their own. “The restaurant fits our personal goal to get to the heart of Italian wine and food,” says executive chef Priolo. “You go to Italy for simple food prepared by hand with local ingredients. We wanted to bring that experience to Chicago.”When the weather allows, enjoy al fresco dining in the hidden garden patio-regularly recognized as one of the best in the city.Starting December 1, Monday-Thursday we'll open at 5 pm rather than 4 pm. You are welcome to bring a cake to celebrate. If you do, we will charge a $3 fee per person cake-cutting fee. Beginning January 1, all credit card transactions will be charged a 3% fee. Starting April 27th, Piccolo Sogno will be taking reservations through Resy. https://resy.com/cities/chicago-il/venues/piccolo-sogno
A photo of Upstairs at The Gwen restaurant
2. Upstairs at The Gwen
4.4
Awesome(425)
$$$$
• American • River North (Chicago)
Booked 22 times today
Experience the premier terrace in River North, located on the 5th floor of The Gwen, a one MICHELIN Key hotel, nestled along the iconic Magnificent Mile! Savor creative cocktails and indulge in delicious small and large plates crafted by Executive Chef Matt Jergens, all while enjoying the warm ambiance of our firepits and the stunning backdrop of towering skyscrapers. Our candlelit indoor lounge and bar offer the perfect setting to unwind, relax, and embrace the good life!Join us on the weekends for Chicago's liveliest, most unique tea service, Tipsy Tea! Featuring scrumptious savory and sweet bites and a special themed menu every month, this is one pinkies-down tea service you will never forget!
A photo of LAUREL restaurant
3. LAUREL
4.1
Excellent(110)
$$$$
• American • River North (Chicago)
Booked 15 times today
LAUREL, nestled in The Talbott, blends New American creativity with Mediterranean flavors, sourcing local and seasonal ingredients. Experience Mediterranean warmth paired with cosmopolitan flair in our full-service yet casual setting, offering a culinary journey for any occasion. Our design pays homage to the Mediterranean's diverse landscapes and artistic influences, creating a modern ambiance. Welcome to LAUREL, where craftsmanship meets creativity, and every meal celebrates flavor, community, and the art of living well.
A photo of Seville Chicago restaurant
4. Seville Chicago
4.8
Exceptional(99)
$$$$
• Mediterranean • Downtown / Loop
Booked 55 times today
Atop the roof of the Hilton Canopy in the Heart of The Loop, Seville is a rustically refined Mediterranean eatery by celebrity chef, hospitality developer and TV personality Fabio Viviani. This signature venue offers seasonally inspired dishes, including elevated takes on his favorite foods, as well as award winning wine offerings and cocktails. Seville features coastal favorites, house-made pastas, Neapolitan-style pizzas, barrel select bourbons, and an extensive wine list.Welcomed by a passionate, knowledgeable hospitality team, guests enjoy this unique elegant, yet approachable restaurant created by combining several sitting options, from comfortable booths and casual bar seating to a outdoor roof deck.Seville by Fabio Viviani Hospitality is perfect for all occasions, from intimate date nights to large dinners with family and friends. We look forward to welcoming you soon.
A photo of The Hampton Social - Streeterville restaurant
5. The Hampton Social - Streeterville
4.5
Awesome(2539)
$$$$
• American • Gold Coast / Streeterville
Booked 103 times today
The Hampton Social - Streeterville is the perfect place to imbibe and enjoy the feeling of summer days. Located in the heart of the Streeterville neighborhood in Downtown Chicago - steps away from shopping on Michigan Avenue. The Hampton Social offers our signature "Rosé All Day" lounge, a lively bar, a second floor covered outdoor terrace, main dining rooms and private dining spaces. Known for our lively dining experiences featuring exceptional coastal-inspired food, cocktails and live music in a beautifully designed atmosphere.Open for Lunch, Dinner, and Weekend Brunch
A photo of Beatrix - Fulton Market restaurant
6. Beatrix - Fulton Market
4.7
Exceptional(2897)
$$$$
• American • West Loop
Booked 119 times today
Beatrix is a neighborhood coffeehouse, restaurant and meeting place in Chicago’s River North, Streeterville, Fulton Market, The Loop and Oak Brook neighborhoods. The restaurant is the brainchild of Lettuce Entertain You Enterprises’ Founder Rich Melman, Executive Partner and Divisional President Marc Jacobs and Chef Partners Andrew Ashmore, Rita Dever and Susan Weaver. The menu features healthy meets delicious options, and is known for its iconic coffee and bakery counter, including signature cookies, in-house pastry favorites and our house blends from Beatrix Coffee Roasters, featuring Light, Dark, Espresso and Decaf roasts.
A photo of Porter Kitchen and Deck restaurant
7. Porter Kitchen and Deck
4.7
Exceptional(468)
$$$$
• American • River North (Chicago)
Booked 59 times today
Porter, located on the Chicago River, features classic American cuisine in an elegant and relaxed setting. The expansive lunch, dinner and bar selections include entrées, fresh seafood, salads and sandwiches — including some of Four Corners' signature favorites. Additionally, the bar serves craft beers, wines and classic cocktails that pair perfectly with the cuisine.
A photo of Bandit restaurant
8. Bandit
4.7
Exceptional(1091)
$$$$
• Bar / Lounge / Bottle Service • West Loop
Booked 31 times today
Bandit is located in the West Loop - Fulton Market neighborhood of Chicago. The DineAmic Hospitality watering hole is a polished-casual restaurant and bar that combines the charm and character of a local neighborhood bar, with the sophistication and quality of an upscale, chef-driven restaurant. The design of the restaurant is a juxtaposition of rustic materials, vintage paraphernalia, and polished décor. It is lowbrow meets high style; glamour meets grit with warm ambient twinkle lights, combined with edgy neon bar signs creating an inviting feel to the restaurant. Nostalgic elements are harmoniously married to elevated attributes throughout the concept in both look and feel, as well as the food and drink presentation.
A photo of Ada Street restaurant
9. Ada Street
4.9
Exceptional(1224)
$$$$
• American • Bucktown / Wicker Park
Booked 28 times today
Located in the Elston Industrial District--not quite Bucktown, not quite Lincoln Park--Ada Street offers dinner service five days a week.
A photo of NoMI restaurant
10. NoMI
4.7
Exceptional(3264)
$$$$
• Sushi • Gold Coast / Streeterville
Booked 47 times today
NoMI, perched above North Michigan Avenue at Park Hyatt Chicago, offers sweeping views of the Water Tower and Lake Michigan. Each “experience” represents a distinct seating area within the venue, NoMI Kitchen, NoMI Lounge, or NoMI Garden, allowing guests to select their preferred setting.NoMI Kitchen features a menu rooted in Midwestern influences, with steaks, housemade pastas, and inventive seasonal dishes. Weekend brunch includes both classic and seasonal favorites.NoMI Lounge offers a full sushi bar, shareable bites, creative cocktails, and an extensive wine list.NoMI Garden, the seasonal outdoor terrace, provides open-air dining with city views and a menu of light fare.

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