Play: Uncovering Chicago Trail by Trail

These scenic walkways reveal a city second to none.

By Jessen O’Brien

In a tiki-themed speakeasy downtown, recent transplant Sasha muses that Chicagoans are tough to get to know. “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 Chicago a “tall bold slugger set vivid against 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 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 skyscrapers lie more than 26 beaches and 570 parks, a generous lakefront and an extensive system of boulevards and paths connecting them. There’s the Magnificent Mile, bordered by 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.

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 (900 North Michigan Shops, level 5, 900 N. Michigan Ave.; 312-649-9373). 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 Elle magazine. Embellished cuffs, clutches and even sleep masks are on display at her dedicated brick-and-mortar store.

Just a block south, the John Hancock Center would immediately stand out for the distinctive X-bracing that covers its exterior if its sheer height, at 100 stories, didn’t grab your attention first. Its 94th-floor observatory, 360 Chicago (875 N. Michigan Ave.; 888-875-8439; adults, $20; children 3 to 11, $13), affords views of four states on a clear day. To explore Chicago from the opposite angle, follow signs that point the way to Billy Goat Tavern (430 N. Michigan Ave., lower level; 312-222-1525; lunch for two, $15*), a gritty burger spot on Michigan Avenue’s subterranean level (the city has several multidecked streets). The original owner, William Sianis, made the dive legendary when he cursed the Chicago Cubs for refusing to admit his pet goat to a World Series game in 1945. Until 2016, the baseball team hadn’t won a World Series since before sliced bread was sold, despite attempts to break the curse by allowing the pair’s descendants onto the field.

Back at the avenue’s main level, you’re within walking distance of some of the city’s most important architecture, including the neo-Gothic Tribune Tower (435 N. Michigan Ave.). Here you can play I Spy, identifying fragments of the Berlin Wall, the Great Wall of China and other famous structures that have been embedded in the 1920s skyscraper while you listen to WGN Radio broadcast from a glass-walled studio on the ground floor. Across the Chicago River, a blue awning marks the meeting place for the Chicago Architecture Foundation River Cruise (meet at the southeast corner of the Michigan Avenue Bridge at Wacker Dr.; 312-922-3432; cruises, from $44 a person). You don’t have to know the 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; dinner for two, $100). Tip: Show up early to snag a table.

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 several Divvy stations (855-553-4889; 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; 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 the Art Institute of Chicago (111 S. Michigan Ave.; 312-443-3600; 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 stately Shedd Aquarium (1200 S. Lake Shore Dr.; 312-939-2438; 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; 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 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; 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.

Afterward you can amble up North Damen Avenue to pick up a pair of kicks at Bucketfeet (1647 N. Damen Ave.; 773-904-8709). People from more than 120 countries have submitted designs for the sneakers (sketch pads and a computer are available on-site for anyone who wants to pitch their own). For a souvenir, check out styles by Chicago-based artists JC Rivera and Matthew Hoffman. A few blocks away, RSVP Gallery (1753 N. Damen Ave.; 773-770-6666) has serious street cred. Kanye West’s creative director, Virgil Abloh, co-owns the shop, which specializes in hard-to-find pieces by international labels like A Bathing Ape and Ambush. It’s worth stepping in just for the collection of pop-art-inspired sculptures by artists such as Jeff Koons and Takashi Murakami.

There’s an entrance to the 606 outside the shop. Heading west, the trail rises to treetop level, passing by apartment buildings and several city parks. Streets below are well marked, and there are even bicycle repair stations for cyclists, one on the trail at North Talman Avenue and two others at ground level, at North Ridgeway Avenue and at Walsh Park. You can hop off at Whipple Street to check out Logan Square gin joint Scofflaw (3201 W. Armitage Ave.; 773-252-9700; drinks for two, $16). Bartenders stir cocktails under Edison bulbs and pass out freshly baked chocolate-chip cookies at midnight.

Two doors down, reservations are required at Giant (3209 W. Armitage Ave.; 773-252-0997; dinner for two, $100), whose name is derived from the Shel Silverstein poem hung on the wall, not the restaurant’s size. Dishes range from the more complicated (Thai chili sweet corn with peanut, scallion, mint and baby shrimp) to the simple but incredible (handmade sortallini pasta with smoky guanciale and basil). End your meal with the cajeta ice cream, two scoops of vanilla coated in a butter-pecan crumble. Much like Chicago, there’s a softness to be found underneath the crunchy exterior if you know where to look.

RCI® affiliated resorts near Chicago include:
Holiday Inn Club Vacations Fox River Resort 4863

Canoe and fish in the seven-acre lake on-property or spend the day on land playing mini golf, tennis or basketball, all within about 70 miles from Chicago. 2558 N. 3653 Rd., Sheridan, IL
Member Review: “Great location and helpful staff.”

RCI® Tip

If you’re planning on taking day trips on your next vacation, did you know you can rent a car through RCI Travel®?** With a Best Rate Guarantee on flights, car rental, hotels and more, RCI Travel can save you the hassle of searching other travel providers.1

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Non-RCI affiliated resorts in Chicago include:
Kimpton Hotel Palomar Chicago

Rooms and suites feature floor-to-ceiling windows and artwork inspired by the Chicago World’s Fair. 505 N. State St.; 312-755-9703;; doubles from $170 a night

Virgin Hotels Chicago

A trendy downtown spot with a speakeasy, lounge and rooftop bar. 203 N. Wabash; 855-946-6600;; doubles from $189 a night

  • *Estimated meal prices do not include drinks, tax, or tip.
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  • Published: Spring 2017