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20 Unique Ways to Spend Your Summer Nights

Spring is fine. Autumn’s pleasant enough. Winter, we will not speak of. But these evening itineraries prove once and for all which is the best season in this city.

Building Blocks
The new rooftop lounge at Celeste

1. Discover the Great Outdoors
Perhaps the only nightlife development more anticipated this year than the opening of hot spot The Dawson was the unveiling of its two-story patio. Designed by BuilderBoone and Heather Shouse of Bottle & Branch, the contemporary yet rustic space features a wooden pergola draped in ivy, a stainless steel bar, a stone fireplace and hickory furniture. Columbines and mums, as well as purple-leaved Japanese honeysuckle vines, create a white and purple motif. There will be herbs planted for the kitchen. But what is served is as much the draw as what is grown: General Manager Clint Rogers is introducing what he calls “vessels,” shared large-format drinks like a tequila punch served in canteens, and in addition to the eclectic menu offerings revelers can expect the occasional crawfish boil. For those celebrating a special occasion, the space is available for rental for $8,000 to $20,000. Our favorite thing about the development, though, can be summed up in four beautiful words: frozen mai tai machine. 730 W. Grand Ave., 312.243.8955

2. Travel to Capri...

“Real men drink pink,” says Bret Heiar, sommelier at Nico Osteria. And as a former competitive Muay Thai fighter, he should know. And you shouldn’t argue. Instead, gather some friends, reserve a private room upstairs in Salone Nico’s cozy bar-above-thebar, and politely ask for the gentleman’s help. His superbly edited list, freshly stocked with pink picks, will satisfy even the most roséreluctant— and his selections, among the best expressions of the varietal, pair beautifully with the acclaimed Italian seafood on offer here. 1015 N. Rush St., 312.994.7100

3. ...Or, Perhaps, to Moscow

This year’s Grant Park Music Festival, the 80th edition, opens June 11 with Russian-born Natasha Paremski at the keyboard for Tchaikovsky’s Piano Concerto. Both piece and performer are fiery and gorgeous. Members of the festival’s Purple Circle ($1,600) sit front and center all season long (and receive other treats, like breakfast with maestro Carlos Kalmar). We recommend getting into the spirit with some well-chilled vodka and an ounce or two of the sturgeon caviar at Russian Tea Time, served (like the concerto) with the classic accompaniments.

4. Start Things Rolling

Serving carts are nothing new to the world of fine dining (a slice of Roquefort, please!), but when it comes to cocktails, the mixologist’s skill and artistry is often relegated to behind the bar. Enter Travelle’s cocktail cart, which brings the action tableside with a rotating selection of drink options. The premier cocktail is the Madhattan, a playful nod to the Mad Men era, when tableside service had its heyday. Guests make their choice from five whiskeys—don’t worry, Travelle’s spirit experts will walk you through each—and their selection is then artfully blended with sweet vermouth, a dash of Benedictine and housemade smoked simple syrup. And while the cart service is available only in the lounge, staff will make an exception if you book the new chef’s table, which can seat up to eight and comes with a seven-course meal ($1,000). But plan ahead: Reservations must be made at least a week in advance, as chef Tim Graham orders exceptional ingredients for this singular experience. 330 N. Wabash Ave., 312.923.7705

5. Have Some Splendor on the Grass

No more throwing elbows! If you love the sweet sounds of the outdoor symphony at Ravinia but loathe the stress inducing, first-come, first-served seating policy, Lawncierge is your remedy. The just-announced VIP experience ($250) includes reserved lawn admission, open-bar service and a delectable dinner buffet with dishes such as chilled lamb loin, and heirloom tomato and feta salad. Other amenities on offer include luxury seating and lighting, as well as a private open-air grill, so guests can socialize under the stars. Speaking of which: With celebrity R&B singer John Legend, folk rocker James Taylor and country sensation Carrie Underwood all set to make appearances, the talent roster is sizzling. But don’t be deterred by the heat; special Lawn Club benefits like chilled towels and frozen sorbet will keep you cool. Another helpful hint? Skip the post-concert mass exodus and book the VIP Classic package on the Valara luxury yacht ($95 per person) to round out the epic evening with fresh jumbo gulf shrimp, a Champagne toast and three hours of cruising—right from the marina at the North Shore Yacht Club.

6. Join the Circus with Rick Bayless

Cascabel, the Lookingglass Theatre Company’s vivid collaboration with chef Rick Bayless, is inherently an immersive experience, featuring a feast and live circus acts. But the opening-night gala for the return of the show, which had its original run in 2012, raises the stakes even higher: The benefit on Aug. 6, co-hosted by Mayor Rahm Emanuel and first lady of Chicago Amy Rule, features a performance of the show with an exclusive dinner and wine pairings. Afterward, the space is transformed into a cabaret with performances by the actors. $1,250, The Goodman Theatre, 170 N. Dearborn St., 773.477.9257 x116

7. Do Chinatown Right

Since he opened Lao Sze Chuan in 1998, chef Tony Hu has been the undisputed king of authentic Chinese cuisine in Chicago, and his empire has since grown to include 11 acclaimed restaurants. But for a truly special occasion, head to his most elegant destination, Chinatown’s Lao You Ju. The space is streamlined and slick, and the sprawling menu loaded with tempting, often exotic dishes. Raise the stakes by calling ahead of time for a private tasting menu in the VIP room. “I’ll take care of them!” Hu promises. We don’t doubt it. 2002 S. Wentworth Ave., 312.225.7818

8. Get This Guy to Cook Dinner Just for You

As executive chef of NoMI Kitchen in the popular Park Hyatt Chicago, Ryan LaRoche has plenty on his plate (both figuratively and literally). But when the idea was tossed around to create a special chef’s table dining experience at the contemporary Mag Mile hotel restaurant, he didn’t hesitate, and the Chef’s Corner concept was born a few months ago. Available Thursday through Saturday evenings with a minimum of four days notice, the customized five-course meal ($150 per person) for up to four diners gives LaRoche the opportunity to expand his culinary wings. “The good thing about the parameters for this is that there are no parameters,” says LaRoche, who, after determining if the party has any allergies or dislikes, begins searching for the best ingredients he can find and then creates dishes that highlight them. Scorpion fish, sea bream and duck heart have all made appearances at previous Chef’s Corner dinners. “I like to source crazy, exotic ingredients,” says LaRoche, whose résumé includes stints at Tru and L’Atelier de Joël Robuchon in Las Vegas. During the meal, diners have plenty of opportunities to interact with LaRoche, as well as sommelier Chad Ellegood, who provides beverage pairings with each course. Before the dinner is over, guests are taken on a private tour of the kitchen. “It’s great to show people where the magic happens at NoMI Kitchen,” says LaRoche. Kitchen confidential, indeed. 800 N. Michigan Ave., 312.239.4030

9. Surround Yourself with Art

At 6,000 square feet, Fulton Market Kitchen has plenty of space for private events. Of the six areas available for intimate affairs at the chic restaurant and lounge, which features contemporary cuisine and creative cocktails, we’re partial to the Private Gallery with its carved wood walls, mirrored ceiling and overall glam vibe. Added bonus: After your customized multicourse dinner, partner Daniel Alonso will give you a tour of FMK’s extensive art collection. Price upon request. 111 N. Sangamon St., 312.733.6900

10. Party Like (and With) a Rockstar

Last year’s VIP offerings at Lollapalooza allowed ticketholders to rub shoulders with the likes of Coldplay and Muse. Not too shabby. But this year’s 2014 Platinum Pass ($3,600) really amps things up. There’s keeping cool and refreshed in the two Lolla Lounges, plus access to the Artist Lounge for meet-andgreets, VIP golf cart shuttles for transport, viewing platforms with premium sightlines, specialty libations and catered meals, mini spa treatments and air-conditioned restrooms. As to after-partying, the Hard Rock Hotel’s bashes have achieved a kind of legendary status. We recommend a stay there, in the two-bedroom Angels and Kings penthouse suite (starting at $1,150), with its upgraded home theater center, custom furniture and artwork from Fall Out Boy Pete Wentz’s personal collection. Glow sticks and sunscreen included. 230 N. Michigan Ave., 312.345.1000

11. Get Saucy with Country Stars

You can’t beat the combo of great barbecue, great music and the great outdoors at the Windy City Smokeout, which takes place July 11-13. Visitors enjoy music from top acts like ACM New Artist of the Year nominee Brett Eldredge while indulging in barbecue from acclaimed spots like Pappy’s Smokehouse in St. Louis. Up the ante with a VIP ticket ($100) providing access to private viewing areas, private restrooms, a private cash bar and barbecue sampling. 560 W. Grand Ave.

12. Let a Chef Mix Your Drink

For chef Riley Huddleston of IO Urban Roofscape, the white cabana- and couch-filled indoor/ outdoor fourth floor-lounge at River North’s new Godfrey Hotel, the decision to bring the cocktail making into the kitchen was a no-brainer. “As chefs, we like to do everything anyways,” he says. Armed with some cool gadgets (liquid nitrogen, pH meters, soda siphons) and scientific know-how, Huddleston, an Aviary alum, and his staff create cocktails that not only taste great but have some fun twists too. Case in point: the beautiful 22-ingredient margarita (pictured) that gets its orange hue from grapefruit and is topped with a habanero-salt foam. And that’s just the beginning. Look for menu appearances soon of white sangria with frozen grapes and ice cubes filled with edible flowers, as well as a chef’s choice lemonade (watermelon ice cubes, anyone?) that’ll evolve all summer long. We feel cooler already. 127 W. Huron St., 312.649.2000

13. Glam It Up, Old School

When Sharp, Clear Pictures: Edward Steichen’s World War I and Conde Nast Years opens this month at the Art Institute of Chicago, we’ll be among the first to visit: The legendary photographer’s iconic portraits of Hollywood royalty shimmer with glamor even now. Best to show up on a Thursday, when the museum stays open late and McKinlock Court will be filled with the sounds of the elegant space’s new jazz series. That’s also where treats from chef Tony Mantuano’s Wine Bar Food cookbook will be offered for the first time. You’ll feel like a star. 111 S. Michigan Ave., 312.443.3600

14. Get Out of Town !

The new Eau de Vie Suite (from $1,780 a night) at the five-star American Club Resort in Kohler, Wis., is a sanctuary with top Kohler spa fixtures. This alone is worth the jaunt, but the much-lauded Immigrant Restaurant, the famous spa and championship golf course make it almost irresistible. Quickest way from point A to B? Your own private Cessna plane from Better Living Aviation ($350/ hour) to Sheboygan, with a short golf cart transfer ($140 roundtrip) that will have you at the first tee in 15 minutes flat. 418 Highland Drive, Kohler, Wis., 920.457.8000

15. Have a Spirited Affair

No matter where you sit at CH Distillery, the beautiful stainless steel stills that create all of the West Loop lounge’s terrific spirits are easy to spot via the large window behind the bar. But for an even better view, we suggest booking the private room in back. Nicknamed The Distiller’s Table, the space can accommodate up to 50 cocktail-loving guests and includes a private bar and dedicated bartender. Choose beverages from off the menu— we’re big fans of the Cease and Desist made with lapsang souchong-infused London dry gin and ginger—or opt for a custom cocktail created by Food and Beverage Director Krissy Schutte. Chef JP Doiron is equally accommodating when it comes to creating a menu from his selection of small plates (don’t miss the house-smoked salmon two ways with buckwheat blinis). After a cocktail or two, learn more about what goes into the spirits in them with a private behind-the-scenes tour from co-founder/distiller Tremaine Atkinson. We hear there are exclusive tastings of CH spirits involved. Don’t say we didn’t warn you. Price upon request. 564 W. Randolph St., 312.707.8780

16. Get Up Close and Personal

Hubbard Street Dance Chicago will no doubt bring in the crowds for its June 6 performance at Harris Theatre with a live simulcast in the Pritzker Pavilion, but a more intimate experience awaits those who score tickets to Inside/ Out ($20, $35 VIP), a choreographic workshop held at UIC Theater, on June 13. Only 160 ticketholders will be able to view the premiere of 12 short works created and performed by the company’s amazingly talented dancers and artistic staff, who mingle with the audience afterward. And don’t rush to leave—rumor has it the dancers are known to invite lingerers to join them at a nearby hot spot. 1044 W. Harrison St., 312.850.9744

17. Sit Pretty

Taking inspiration from the historic, four-story building it’s housed in, River North cocktail lounge/restaurant Celeste features some of the coolest design details in town. Whether sitting on a cushy stool at the first-floor bar or a table in the second-floor Deco Room, you’ll find plenty of eye candy—ornate mirrors, gold-leaf ceilings, monogrammed glass walls, Louis Sullivan-inspired iron work—to go with your perfectly made craft cocktail. No surprise, then, that its new fourth-floor rooftop is just as elegant. Inspired by a refined English garden, the 85-person-capacity space includes tabletop terrariums, a pewtertopped bar, and cream-colored Victorian couches and chairs. Ivy-covered brick walls and vines overhead add to its charm. Throw in some vintage-inspired punch bowl cocktails and tasty small plates and this newcomer has “save us a seat” written all over it. Available for private parties; price upon request. 111 W. Hubbard St., 312.828.9000

18. Stargaze with Style

With one of the city’s best outdoor lounges—the stunning lake and river views alone are worth a visit—it comes as no surprise that The Terrace at Trump takes its beverage program very seriously. “We started tasting cocktails and planning the opening back in February,” says Food and Beverage Manager Mauricio Kuri. The extra effort has paid off. This year visitors to the 16th-floor space at the luxe hotel, which changes things up at The Terrace every season, can look forward to not one, but two menus of ubercreative cocktails with an emphasis on spirits from around the world and hard-to-find ingredients. Take their version of a Manhattan, for example. With the addition of Campari ice cubes, it becomes a different cocktail—a Boulevardier—once the cubes melt. Kuri’s also excited about the Sacred Lotus, which combines sochi with rooibos tea and Griffard grapefruit liqueur from France. An atomizer filled with rosewater finishes the drink tableside. And after sunset, a reserve list of cocktails presented in handmade ice sculptures instead of glasses and served with straws is available as well. If you don’t see what you’re looking for, just ask. Says Kuri, “We always try and accommodate special requests.” We like how you roll, Donald. 401 N. Wabash Ave., 312.588.8600

19. Enjoy Dinner with a View

Perched on the 17th floor of Public Chicago, the Ava room, one of the city’s most exclusive hidden gems, has a 645-square-foot terrace with stunning views of the Chicago skyline. Whether it’s an intimate dinner for two or a feast for 20, the hotel’s expert staff will ensure your night will be memorable. Inside tip: Inquire whether Pump Room’s New York-based chef, Jean-Georges Vongerichten, can be flown in to work his culinary magic. Price upon request. 1301 N. State Parkway, 312.787.3700

20. Go Gaga!

Thousands of music-lovers will descend on United Center when Lady Gaga comes to town on July 11 for the Chicago leg of her ArtRave: The Artpop Ball tour. Make sure you score some face time with Mother Monster herself by opting for the Artpop Zone Package (now on resale market), which offers not only a prime seat for the concert, but access to a private lounge for a post-show meet-and-greet and photo op. 1901 W. Madison St., 800.653.8000