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A view of downtown from the Lakefront Trail. Below: A river cruise passes by one end of the Magnificent Mile; the North Side’s elevated 606 path.

n a tiki-themed speakeasy downtown, recent transplant Sasha muses that Chicagoans are tough to get to know. Uncovering I“Everyone’s friendly, but it takes time,” she says. That steely spine is a quality the people share with their city. Poet Carl Sandburg called a “tall bold slugger set vivid against Chicago the little soft cities,” and writer Nelson Algren noted that Chicago’s charms are less polished than some but insisted “once you’ve come to be part of this particular patch, you’ll never love another.” Getting to know Chicago is well worth the effort. Time your Trail by Trail visit with the spring, when residents peel off their puffy coats for a long-awaited reunion with the city’s many outdoor pleasures. Below its stone lie more than 26 beaches and 570 parks, THESE SCENIC WALKWAYS REVEAL a generous lakefront and an extensive system of boulevards and A CITY SECOND TO NONE. paths connecting them. There’s the Magnificent Mile, bordered by

BY JESSEN O’BRIEN landmark buildings and glamorous boutiques; the Lakefront Trail, which passes by several top-notch museums; and the 606, a former rail line recently converted into a lush corridor through Chicago’s trendy North Side. Those who take the time to explore these urban trails will discover the city’s many green spaces as well as an array of other qualities that give Chicagoans their characteristic pride: extraordinary architecture, an exciting but unassuming food scene and a remarkable number of world-class cultural institutions.

ENDLESS VACATION 31 The Magnificent Mile Chicago’s most celebrated boulevard stretches almost a mile along Michigan Avenue, running from the Chicago River north to Oak Street. The northern end is filled with many of the luxe brands that the Magnificent Mile is known for: Gucci, Louis Vuitton and Chanel all sit within two blocks. When you’re ready to move from window-shopping to browsing, make your way to Azeeza ( Shops, level 5, 900 N. Michigan Ave.; 312- 649-9373; azeeza.us). Since leaving a job in corporate marketing about five years ago to pursue fashion, local Azeeza Khan has designed clothing and accessories worn by Sarah Jessica Parker and highlighted in Jeweled sleep masks Elle magazine. Embellished cuffs, clutches at Azeeza. and even sleep masks are on display at her dedicated brick-and-mortar store. Just a block south, the would immediately stand out for spot on Michigan Avenue’s subterranean city’s most important architecture, the distinctive X-bracing that covers its level (the city has several multidecked including the neo-Gothic Tribune exterior if its sheer height, at 100 stories, streets). The original owner, William Tower (435 N. Michigan Ave.). Here you didn’t grab your attention first. Its 94th- Sianis, made the dive legendary when he can play I Spy, identifying fragments of floor observatory,360 Chicago (875 cursed the Chicago Cubs for refusing to the Berlin Wall, the Great Wall of China N. Michigan Ave.; 888-875-8439; 360chicago admit his pet goat to a World Series game and other famous structures that have .com; adults, $20; children 3 to 11, $13), in 1945. Until 2016, the baseball team been embedded in the 1920s affords views of four states on a clear day. hadn’t won a World Series since before while you listen to WGN Radio broadcast To explore Chicago from the opposite sliced bread was sold, despite attempts from a glass-walled studio on the ground angle, follow signs that point the way to to break the curse by allowing the pair’s floor. Across the Chicago River, a blue Billy Goat Tavern (430 N. Michigan Ave., descendants onto the field. awning marks the meeting place for the lower level; 312-222-1525; billygoattavern Back at the avenue’s main level, you’re Chicago Architecture Foundation .com; lunch for two, $15*), a gritty burger within walking distance of some of the River Cruise (meet at the southeast corner of the Michigan Avenue Bridge at Wacker Dr.; 312-922-3432; architecture.org; cruises, from

X-bracing crisscrosses $44 a person). You don’t have to know the the John Hancock Center. name Ludwig Mies van der Rohe to enjoy this engrossing 90-minute tour, which describes the city’s development through architectural milestones. Nearby you’ll find Mediterranean fare and an extensive wine list at the no-reservations Purple Pig (500 N. Michigan Ave.; 312-464-1744; thepurplepigchicago.com; dinner for two, $100). Tip: Show up early to snag a table.

Explore one more walking trail in the new mobile-friendly Endless Vacation® magazine app. See page 6 for details!

32 SPRING 2017 *Estimated meal prices do not include drinks, tax or tip. The Lakefront Trail Forget about tackling the Lakefront Trail in a day. The path wraps 18 miles around Lake Michigan and offers Instagrammable views of the city sweeping up from the shore as sailboats drift in the foreground. You can rent a bike from one of severalDivvy stations (855-553-4889; divvybikes.com; rentals, $10 a day) to explore a larger swath of the trail (remember to bring your own helmet). Otherwise, stroll along the lower paths that run parallel to the main trail, which primarily serves runners and anyone on wheels. You can fuel up at Revival Food Hall (125 S. Clark St.; 773-999- 9411; revivalfoodhall.com; lunch for two, $40). Less than a year old, the marketplace houses 15 stalls, many of which are downtown spin-offs of popular North Side eateries, such as Antique Taco and ramen shop Furious Spoon. Once you’ve had your fill, head to theArt Institute of Chicago (111 S. Michigan Ave.; 312-443-3600; artic .edu; admission, $25). With about 300,000 works in its collection, the museum has more than its fair share of must-sees. One high point: The miniature rooms on the lower level depict in scrupulous detail European and American interiors dating back to the 13th century. If you exit the museum from the modern-art wing, you can turn right on Monroe Street to reach the Lakefront Trail. (Alternatively, detour across the Nichols Bridgeway to Millennium Park for a quick photo op at Anish Kapoor’s Cloud Gate sculpture, a.k.a. the Bean.) Heading south on the trail, it’s about a mile to the statelyShedd Aquarium (1200 S. Lake Shore Dr.; 312-939-2438; sheddaquarium .org; adults, $31; children 3 to 11, $22). Here, a scuba diver in the Pritzker Caribbean Reef tank hosts daily Q&A sessions while swimming among puddingwives, saucereye porgies and other memorably named fish. Like the Shedd, the nearby Adler Planetarium (1300 S. Lake Shore Dr.; 312-922-7827; adlerplanetarium.org; adults, $12; children 3 to 11, $8) was built in 1930 and attracts long lines so it’s advisable to buy tickets in advance. Consider signing up for a tour of the Atwood Sphere, a planetarium that shows what the sky over Chicago looked like in 1913.

The 606 The two-year-old 606 (the606.org) provides an elevated walkway and cycling path that runs almost three miles east–west from Ashland Avenue to North Ridgeway Avenue through several up- and-coming North Side neighborhoods: Wicker Park, Bucktown, Logan Square and Humboldt Park. You’ll find a microcosm of all four at Dove’s Luncheonette (1545 N. Damen Ave.; 773- 645-4060; doveschicago.com; brunch for two, $30), where young professionals and working moms with kids in tow gather over homey Tex-Mex while the jukebox croons Etta James. Although the Wicker Park diner looks like a local institution from the 1960s, it opened three years ago under Paul Kahan, a three-time James Beard Award–winning chef.

From top: Painter Georges Seurat’s A Sunday on La Grande Jatte—1884, at the Art Institute of Chicago; the Lakefront Trail leads to several beaches; sneakers and artwork on display at Bucketfeet, near the 606. PHOTOS, OPENING PAGE, CLOCKWISE FROM LOWER LEFT: CHOOSE CHICAGO (2); JESSEN O’BRIEN; SECOND PAGE: JESSEN O’BRIEN (2); THIRD PAGE: CHOOSE CHICAGO (2); JESSEN O’BRIEN; THIS PAGE: GALDONES PHOTOGRAPHY underneath thecrunchy exteriorunderneath to where ifyouknow look. pecan crumble.Much like asoftnessto Chicago,there’s befound with the sortallini shrimp)to mint andbaby thesimplebutincredible (handmade chilisweetcornwithpeanut, scallion, more complicated (Thai range from the hung onthewall,notrestaurant’s size.Dishes $100 Armitage Ave.; 773-252-0997;giantrestaurant.com; fortwo, dinner and passoutfreshly baked chocolate-chip cookiesatmidnight. for two,$16 ( Streetat Whipple to checkoutLoganSquare ginjoint at North Ridgeway Avenue andatWalsh Park. You canhopoff trail atNorth Talman Avenue atground level, andtwoothers oneonthe stationsforcyclists, repair bicycle are even and there cityparks. arebuildings andseveral wellmarked, Streets below west, thetrail risesto treetop apartment passingby level, and Takashi Murakami. of pop-art-inspired artistssuchasJeff sculptures by Koons and Ambush.It’s worthstepping injustforthecollection to-findby international pieces labelslike ABathingApe theshop,whichspecializesinhard- Virgil Abloh,co-owns .com RSVP Gallery Hoffman. blocks Afew away, andMatthew artists JCRivera Fortheir own). asouvenir, Chicago-based checkoutstylesby a computer are available on-site foranyonewhowantsto pitch have submitted designsforthesneakers (sketch padsand 8709; bucketfeet.com up apairofkicksat 3201 W. Armitage Ave.; 773-252-9700;scofflawchicago.com; drinks Two doors down, reservations are requiredTwo reservations at doorsdown, to anentrance There’s the606outsideshop. Heading Afterward youcanambleupNorth Avenue Damen to pick and jalapeño Giant’s bacon ) has serious street cred. Kanye) hasserious West’s creative director, ), whose name is derived from the Shel Silverstein poem from theShelSilverstein), whosenameisderived poem pastawithsmoky cajeta ). Bartenders stir cocktails under Edison bulbs ). Bartenders Edisonbulbs stircocktailsunder pici

icecream, twoscoopsofvanillacoated inabutter- ( pasta. 1753 N. Damen Ave.;1753 N. 773-770-6666;rsvpgallery Damen Bucketfeet ). People from more than120countries guanciale ( 1647 N. Damen Ave.;1647 N. 773-904- Damen and basil). End your meal andbasil).Endyourmeal Giant Scofflaw ( 3209 W.

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