Cupid hearts Volo. Draw the sheer curtains across one of the cabanas at this Roscoe Village eatery (left), and this candlelit enclave (6 miles northwest of the Loop) will make you feel as if you've stepped into a romance novel.
Though the cabanas are perfect for date night, owner Jon Young is equally passionate about welcoming singles and groups to the back patio, where wrought-iron tables and cedar banquettes also offer charming ambience.
The menu will make you fall for a 2006 Argentine champagne ($10 a glass) and sweet pea flatbread ($10). Fresh oysters (market price) are worth the commitment. The duck confit ($20) has been marinated for 12 hours and slow-cooked for another 12.
Landscape artist Helene Albert surrounds diners with a perfect pair of raised gardens, a century-old barn and a patio fountain. At dusk, hanging paper lanterns create an illuminated fairyland. And the name? It comes from the Latin word for "flight"--which the heart takes with every visit.
Volo, 2008 W. Roscoe Street, Chicago (773/348-4600).
Shanghai Terrace's doting staff, swank decor and traditional Chinese cuisine await at this Peninsula Hotel restaurant four stories above Michigan Avenue. Flowering trellis screens divide the spacious patio (left) into intimate dining and lounging areas, complete with plump couches and daybeds draped in flowing sheers.
Pleasantly exotic, the cooking uses all organic ingredients, spices and herbs. A dim sum sampler appetizer offers a shrimp spring roll, crispy scallop, lobster dumpling, spicy beef gyoza, peeky crab wonton and foie gras dumpling ($18). A seafood wonton and noodle soup satisfies small appetites ($14), while a crispy duck entree comes with Chinese long beans and tangy homemade hoisin sauce ($32).
Reservations recommended. Shanghai Terrace, 108 E. Superior Street, Chicago (312/573-6744).
Shanghai Terrace 
Patrons of Park Grill, centered in Millennium Park, can catch glimpses of themselves in the famous Cloud Gate sculpture (better known as the Bean; pictured at left). The eatery has two sit-down outdoor restaurants: Prairie-style Park Grill and the casual Plaza at Park Grill.
At the sophisticated Park Grill, South Side native and Chef Bernie Laskowski serves his take on American classics and traditional ethnic dishes, such as the falafel with wheatberry salad ($12) and creamy carbonara pasta with a slice of crisp pork belly on the side ($18). Other winners: watermelon gazpacho topped with shredded crab ($5) and the wild mushroom flatbread ($11). Can't choose a dessert? The cookies, candies and chocolate plate offers two of each ($5).
Most of the food at the Plaza at Park Grill is grilled. Duck taco appetizers wrapped in homemade tortillas make a light meal ($10); so does the grilled peach salad ($8). Entrees ($10-$18) include burgers, sandwiches, sea scallops with red pepper chutney and apricot-thyme glazed chicken. Lemon meringue parfaits are $5. A silver almond bean garnishes the signature "beantini" cocktail.
Park Grill, 11 N. Michigan Avenue, Chicago (312/521-7275).
Park Grill 
Camels forage for lunch in a leafy enclave across the street at the Lincoln Park Zoo while patrons dine on beautiful French cuisine at Mon Ami Gabi (left). Shaded by white ash, peach and crabapple trees in a garden of begonias, daylilies and verbena, this bistro is great for a post-zoo meal of French comfort food.
Satisfying, under-$20 entrees include thyme-crusted salmon ($16.95) and a robust, flavorful steak steeped in peppercorn sauce ($19.95). Diners in the 75-seat patio can see chef/owner Gabino Sotelino snipping fresh sprigs of mint, basil and rosemary. Landscape artist Willis Lane nurtures the herb garden alongside tea rose bushes and flowering hibiscus.
Mon Ami Gabi, 2300 N. Lincoln Park West, Chicago (773/348-8886).
Mon Ami Gabi 
An ultrachic crowd sips organic cocktails (left) and nibbles sushi at ebony woven-wire tables in NoMI's Garden, a casual patio just off NoMI restaurant (named for its North Michigan Avenue location) on the seventh floor of Chicago's Park Hyatt Hotel. In the evening, the surrounding skyscrapers shimmer in the setting sun.
A mix of jazz and techno music floats from hidden speakers near planters of swaying grass. The large sushi rolls ($23) and enticing small plates ($12-$18) of grilled sausages, seviche and a Spanish cheese flight encourage sharing. Standout desserts include the peaches-and-cream ice cream bar ($8). On weekends, NoMI Garden is open until midnight for late bites and moonlight nightcaps.
NoMI, 800 N. Michigan Avenue, Chicago (312/239-4030).
The lush grounds surrounding a Victorian farmhouse-turned-restaurant (left) lure visitors to Enzo and Lucia in suburban Long Grove (35 miles northwest of the Loop). "It reminds me of Italy," says Lucia Cavallino, who learned to cook in her native Naples, helping her mother concoct the perfect marinara. "As kids, we'd have big family meals outside. The little ones would play by the fountains, run around on the grass."
Cavallino recipes are family heirlooms. Enzo and Lucia's sons, Angelo and Gennaro, make fresh pasta daily and serve polla alla Enzo (chicken layered with fontina cheese and asparagus, $17.95) and scampi Lucia (shrimp and clams bathed in Lucia's top-secret blend of garlic, spices and olive oil, $22.95). Early mornings, Enzo scours local farmers markets while Lucia concocts her famed tiramisu ($7).
Enzo and Lucia, 343 Old McHenry Road, Long Grove (847/478-8825).
Enzo and Lucia 
The Chicago skyline fills the view, but it's the emerald waters of the Mediterranean Sea that inspire Yiannis Melidis, owner of Pegasus in Chicago's Greektown, about a mile west of the Loop. Born on the Greek Isle of Patra, Yiannis grew up "50 feet from the ocean" and wanted his 160-seat place to capture a picnic feel.
"We ate from the sea every day. My mother and my aunts--all of their recipes are on our menu," Yiannis says. That includes grilled shrimp, spicy and skewered ($9.75) and squid steeped in wine and stuffed with spinach and feta cheese ($8.85).
Under sky-blue canopies shading linen-draped tables (left), diners pass small plates of fish-roe spread ($6.25), lamb chops ($12.95), gyros or pork kabobs ($7.75 each). If you start dinner at twilight, by the time dessert arrives you'll also get a truly spectacular view of the city as it lights up the sky.
Pegasus, 130 S. Halsted Street, Chicago (888/558-2637).
Say you have a taste for a frosty pint of banana-bread beer and a congenial, Cheers-like atmosphere under a setting sun. Then head to the beer wunderland known as Palmer Place Restaurant and Biergarten in suburban La Grange (15 miles southwest of the Loop). A backyard garden teems with umbrella tables (left), while a 260-seat rooftop terrace overlooks downtown La Grange. This 25-year-old place is always packed, maybe because it feels like everybody knows your name, even if they don't.
Don't know beer and lager from ale and stout? Owners Phil and Steve Palmer are happy to explain the differences between the likes of Pendle Witches Brew and Belgium Brewing Skinny Dip. You'll also find household names among the 36 on-tap and 250 bottled selections.
Of course, good beer calls for good pub grub. Try the half-pound Angus cheeseburger ($8.50) or the English muffin crab melt ($12.95).
Palmer Place, 56 S. La Grange Road, La Grange (708/482-7127).
(A version of this story appeared in Midwest Living® July/August 2009.)
Palmer Place