Best Of Chicago

Best Outdoor Dining In Chicago

July 18, 2012 6:00 AM

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Photo Credit: Three Aces via Facebook

Photo Credit: Three Aces via Facebook

By Elizabeth SanFilippo

Summer doesn’t last long in the Windy City, so take your meal outside when you can. The outdoor dining scene is huge in Chicago, what with so many restaurants adding chairs outside when the weather grows warm. But outdoor dining is just as much about ambiance–and occasionally people watching–as it is about the food.

big star chicago via facebook Best Outdoor Dining In Chicago

Photo Credit: Big Star Chicago via Facebook

Big Star
1531 N Damen Ave
Chicago, IL 60622
(773) 235-4039

While Big Star recently extended the size of its indoor space by taking some from the patio, outdoor dining in Chicago doesn’t get much better than this, in part because it’s open until 2 a.m. most nights and 3 a.m. on Saturday. In the heart of Wicker Park, Big Star’s patio is the perfect place for gourmet Mexican food like saucy pork belly tacos, creamy guacamole to go with your chips and a flavorful Sonoran hot dog (which just might be too big for one sitting). Arrive early, because this trendy patio is sure to be packed.

deleece grill Best Outdoor Dining In Chicago

Photo Credit: Deleece Grill

Deleece Grill Pub
3313 N Clark St
Chicago, IL 60657
(773) 348-3313

When warm weather hits, head to Deleece’s Clark Street location for a great dining experience. Unlike most al fresco dining spots in the city, this patio is located at the back of the restaurant, creating the feel that you’re hanging out in a friend’s backyard rather than at a charming restaurant. But this is no simple barbecue, because Deleece offers a great whiskey selection as well as some mouth-watering mac-n-cheeses on the garden patio (which fits 60 guests). The pub is open for dinner throughout the week (closed Mondays) as well as for brunch on weekends. You can also grab a late lunch here on Cubs home game days.

Related: The Best Chicago Rooftop Bars

piccolo sogno Best Outdoor Dining In Chicago

Photo Credit: Piccolo Sogno

Piccolo Sogno
464 N Halsted St
Chicago, IL 60642
(312) 421-0077

At the corner of Halsted and Grand, one wouldn’t expect a gorgeous patio, but that’s exactly what you’ll find at Piccolo Sogno, which means “little dream” in Italian. In fact, out on the spacious patio sparkling with Italian lights at night, you’ll feel like you’ve been swept away to Italy. This romantic spot is also great for food, too; try classic and seasonal Italian dishes like hand-tossed pizzas and pappardelle con cinghaile (wild boar pasta). No matter how filling the dishes, don’t pass by the divine desserts, and that includes the gelato, a perfect summertime treat.

three aces via facebook Best Outdoor Dining In Chicago

Photo Credit: Three Aces via Facebook

Three Aces
1321 W Taylor St
Chicago, IL 60607
(312) 243-1577

This gastropub in Little Italy doesn’t offer your typical bar foods, nor does it have a typical patio. While it may look like a biker/rock-n-roll bar, it offers upscale dining at reasonable prices, such as a pork belly bowl for $15. The stellar outdoor patio has taken over the pub’s parking lot, spreading across 2,500 square feet, and features picnic tables for seating. Three Aces offers both brunch and dinner out on the patio; order its bolognese fries, similar to a poutine, with an amazing thick meaty sauce on top.

turquoise cafe via facebook Best Outdoor Dining In Chicago

Photo Credit: Turquoise Cafe via Facebook

Turquoise Cafe
2147 W Roscoe St
Chicago, IL 60618
(773) 549-3523

The simple ambiance inside Turquoise Cafe is charming and relaxing, but it’s the beautiful sidewalk patio that makes it a wonderfully romantic destination in the heart of Roscoe Village. After all, despite being on the sidewalk, it still feels intimate and serves as a wonderful place to people watch. The cafe is also known for offering the best Turkish food in the city, as well as a few Italian and Mediterranean dishes, from delicious starters of lahmacun to hearty entrees of lamb begendi and salt crust Mediterranean porgies.

Related: Waterside Dining Guide

Elizabeth SanFilippo is a freelance writer, who enjoys trying new foods from all over the world. But her favorite city for culinary treats will always be Chicago. When not writing about food, she’s scribbling novels, and TV show reviews and recaps. Her work can be found at

View Comments
  • Best restaurants in Chicago Little ItalyThe Working Mom's Travels

    […] Best place to go without the kids: Three Aces. I make it no secret that Three Aces is my favorite place in the entire city of Chicago. Since it is in Little Italy, naturally I had to include it on this list! One thing I love most about this “rockabilly gastropub” is its tagline: “The Italian countryside meets the American farmhouse… in Keith Richards’ basement bar.” The description is fitting and it’s the main reason I suggest leaving the kids at home. Mom and Dad need the chance to fully enjoy the outstanding beer and liquor selection at Three Aces, consisting mainly of American craft beers and spirits. While the setting definitely leans more toward the bar atmosphere, it’s the food at Three Aces that steals the show. The farm-to-table menu is divided into four main sections (Farm, Mill, Sea, and Barn), features local ingredients, and changes seasonally. The menu also includes year-round staples like pizzette (personal pizzas) and bolognese fries (one of my favorite dishes). Also, the outdoor patio at Three Aces is one of the best in the city. […]

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