Al Fresco Dining: Hot List For Chicago's Coolest Places

Al Fresco Dining: Hot List For Chicago's Coolest Places
NoMI Garden at Park Hyatt, 800 N. Michigan Ave. just one of many Chicago choices for outdoor dining

Al Fresco dining season 2015 is open with something for everyone from the pricey rooftop offerings on Sixteen’s Terrace in Trump Tower to hot dogs at Wiener Circle.

Every year for the past four years Show Me Chicago has put together a list of our favorites. For 2015, we are taking a look at some of our favorites–new and old.

1. Chicago Cut

Chicago Cut overlooking the Chicago River and skyline

Chicago Cut overlooking the Chicago River and skyline

Although not brand new, Chicago Cut’s (300 N LaSalle) spacious outdoor patio overlooking the Chicago River should be better than ever this season due to the spiffing up of Chicago’s Riverwalk below. “Cut” is a celebrity magnet attracting politicians including the Prez (Obama), actors and the biggest stars in sports—don’t be surprised if you run into a Blackhawk or two including Chicago’s latest Darling–and maybe (cross your fingers) even Stanley–after all he’s been there before.

On the menu: 100% USDA Prime Beef, dry aged for 35 days in a trendy, fun atmosphere.

2. Virgin Hotel

Spacious outdoor space atop the Virgin Hotel

Spacious outdoor space atop the Virgin Hotel. Photo: Nick Fochtman.

Chicago’s newest rooftop, Cerise–meaning cherry red–is scheduled to open today (April 29). Located on the very top of the hotel 26 stories up, Virgin Hotel’s CEO Raul Leal, says “now that Chicago has thawed out from the winter, it’s time to unveil the cherry on top.” It seems, the people at Virgin have a good sense of humor–virgin/cherry. The spacious rooftop that spans the entire width of the hotel includes a terrace that wraps around three sides, two bars, magnificent city views and a colorful assortment of plush seating.

On the menu: An Izakaya inspired menu (Japanese pub) offers salty, spicy, crunchy and savory small dishes. The drink menu offers shared or individual drinks. You can sip their signature Tradewinds Punch with up to six of your best buddies or savor their Far East Gimlet all for yourself.

 3. Piccolo Sogno
Piccolo Sogno--a courtyard getaway--in the middle of busy West Town

Piccolo Sogno–a courtyard getaway–in the middle of busy West Town

Somehow I missed this spot which has been around since July of 2008 until last summer—shame on me. Piccolo Sogno which means “little dream,” in Italian, is definitely in the running for my top spot to dine outdoors in the city. Its tree-laden courtyard setting, aglow with twinkling lights, is located in the hustle and bustle of West Town but has the feel of a country estate–perhaps the Italian countryside.

On the menu:  Piccolo Sogno features a menu of fresh, seasonal rustic Italian cuisine and regional Italian dishes – from homemade pastas and hand-tossed, wood-fired pizzas to Roman-style pork and Mediterranean sea bass – plus homemade gelato and sorbet complimented by an impressive all-Italian wine list.

Piccolo Sogno’s Little sister, Piccolo Sogno Due, which opened on Chicago’s riverfront in 2012 in the River North neighborhood offers a 34-seat street-side patio reminiscent of an Italian café featuring Italian cuisine and a very good wine list.

4.  Petterino’s

alfrescopetterinosPetterino’s (150 N Dearborn St.), named after beloved Arturo Petterino, maitre d’ from Chicago’s gloried past, has an old school vibe inside with its rich wood accent, big bar, celebrity caricatures, soft lighting, white table cloths and red leather booths—while outdoors it offers one of the few “downtown” outdoor patios where you can watch the maddening crowd–rushing to catch the 5:07 to the burbs, or the latest offerings at the Goodman, Oriental or Cadillac Place Theaters–while you leisurely sip one of their classic cocktails—from their spiced cucumber Tom Collins to the Windy City Martini—three blue cheese olives please.

On the menu:  Classic Italian dining, prime steaks and fresh seafood. On a budget, get their blue cheese and bacon laden wedge salad ($8.95) and a drink.

5. River Roast

Guest can arrive via the water at Chicago's popular River Roast.

Guest can arrive via the water at Chicago’s popular River Roast.

The hot, River Roast, in its prime locale overlooking Chicago’s riverfront rings in its second summer of outdoor dining from James Bread award-winning Chef/Partner Tony Mantuano.  Great food and great music including their popular Blues & Brews Brunch keeps the crowds coming.  Their attractive patio provides a front row seat for all the action on the river. Better yet, even if you don’t own a boat, you can arrive by water. Just hop aboard the water taxi by the Wrigley Building or Ogilvie Station and disembark at the Roast.

On the menu: Rustic, shareable roasts, whimsical cocktails

6. Fig and Olive

Two of my favorite foods, figs and olives, is the theme of this Oak Street dining destination that transports diners to the French Riviera both inside the restaurant and outside on their open-air garden terrace which features an LED-lit living wall.

Fig and Olive--a little piece of South France in the Windy City.

Fig and Olive–a little piece of South France in the Windy City. Photo: FIG & OLIVE.

On the menu: Fig and Olive is passionate about their olive oils which feature flavors from the Riviera and Coastal regions of the South of France, Italy and Spain. Start your meal off with an assortment of cheeses served with Fig Jam and Marcona Almonds and/or a sampling of mixed olives from Spain and France.  Then go for some of  their beautifully ripen figs drizzled with gorgonzola cheese and honey. Next select from their menu of Mediterranean inspired mains followed by dessert–perhaps, a caramelized apple tart.  Over 30 varietals of wine from the South of France, Italy, and Spain are offered by the glass or bottle to complement your meal.  Open for lunch, brunch, dinner.

7. Gibsons

Gibsons Steakhouse is a Chicago icon…25 years and counting and people still wait in line, sometimes for two hours or more to get a table on Gibsons prized patio on a beautiful summer night. The food is very good, but it’s more about the scene at Gibsons. Located on Chicago famed Rush St., a seat on the patio offers a spot to see and be seen. You’ll rub shoulders with local power brokers, celebs and “the regulars” who think of the restaurant as their private club.

On the menu: Big flavor steaks and chops, along with the typical steak house sides including a delicious creamed spinach. You’ll also find an outstanding selection of seafood creations such as spicy lobster cocktail and Alaskan Red King crab cocktail. Known for their generous-sized cocktails—you may only need one.

8. Waterfront Cafe

Waterfront Cafe--an in town getaway.

Waterfront Cafe–an in town getaway.

Right on the lake, the aptly named Waterfront Cafe (6219 N Sheridan Rd.) offers a seaside vacation escape minutes north of downtown, with live music—5 nights a week, fantastic lake views in a relaxing atmosphere.  Located alongside a charming coach house—that offers plays some evenings in the summer—the setting provides a welcoming in-town getaway.

On the menu: Reasonably priced salads, homemade guac, crab cakes, wraps, a kids menu, beer, wine and mixed drinks.

9. Little Goat

Little Goat's rooftop--a perfect spot for warm weather dining.

Little Goat’s rooftop–a perfect spot for warm weather dining.

The Little Goat offers a laid back atmosphere in the popular West Randolph Street restaurant district.  The  Goat—sister to Stephanie Izard’s insanely popular Girl and the Goat–provides guests with a place in the sun—or under the stars—on their comfortable rooftop deck.  On weekdays, the roof’s open for lunch-goers to bring up their sandwiches from Little Goat Bread and enjoy them on the roof.   Dinner and weekends offer table service and an outdoor bar. 820 West Randolph Street.

On the menu: The “Bakery Menu” (6 a.m. to 6 p.m.) offers custom creations, sandwiches, muffins, scones, great breads and more.   Evenings and weekends bring cocktails, beer and bubbly to the table plus bites such as olives or ceviche along with creative entrees and desserts.

10. Uncommon Ground on Clark

Uncommon dining in the heart of Wrigleyville.

Uncommon dining in the heart of Wrigleyville.

Deep in the heart of Wrigleyville, Uncommon Ground, offers the antithesis of ball park hot dogs and nachos with their uncommonly healthy, creative and tasty menu especially when enjoyed on their leafy green patio—a farm in the city.  Just in time for derby day, diners can savor fresh mint from the patio for mint juleps or their mojitos. Open for breakfast (hours vary), lunch and dinner.

One the menu: The menu is centered around seasonal, locally produced, family farmed and organic products. The breakfast menu offers a tasty selection of breakfast omelets, corn beef hash and vegetarian and vegan offerings including vegan chilaquiles and severson farm organic hulled oatmeal with fisher farm organic maple syrup, dried sweet cranberries and house-made granola—I loved—and I don’t even like oatmeal. The lunch and dinner menus are equally as tasty and creative. The drink menu offers an interesting selection of beers, wines and cocktails.

Click here, to see last year’s picks.

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