There’s this running joke Chicagoans like to tell: Don’t like the weather? Wait fifteen minutes. A generous interpretation is that in Chicago, there’s always a good reason to spend time outside.
Chicago is a true four-seasons town: Summers are glorious here, a place where it seems like a block party or softball tournament is always taking place. Fall foliage can be as vibrantly yellow and red as New England’s. Around the holidays, a few laps around the Ice Skating Ribbon at Millennium Park is a magical experience. And at first thaw, the Lake Michigan shore becomes repopulated with runners—the city even shuts down Lake Shore Drive once a year, turning its scenic sixteen miles into a bicyclists-only pathway.
Complaints that Chicago is too hot, too frigid, or too windy are overblown (we will accept that our topography is too flat, fine). Any excuse to get outdoors is one we’ll take advantage of, and once all that energy is spent, we’ve got some of the nation’s best options for good food and total relaxation at our fingertips.
Parks and Beaches
1. Northerly Island
1521 S. Linn White Dr., Chicago
Like London’s Hyde Park or New York’s Central Park, new-to-town runners in Chicago gravitate to Millennium Park and Grant Park, the expansive green space downtown surrounded on three sides by skyscrapers. What most out-of-towners don’t know? Keep running south toward Soldier Field, turn east toward the Museum Campus, and you’ll arrive at the most stunning vista the city offers. Northerly Island was once Meigs Field, an airport that jutted out into Lake Michigan. Today, it’s a peaceful if under-appreciated forty-acre park with well-kept walking and biking trails, circling a lagoon that’s ever-popular with migratory wildlife.
2. Steelworkers Park
87th and Lake Shore Dr., Chicago
A stone’s throw from the Indiana border is this serene lakeside park, part of Chicago’s ongoing efforts to revitalize sites abandoned by the once-mighty steel industry. Formerly part of the U.S. Steel Corporation, the converted Steelworkers Park is all walking paths and lake views, anchored by an imposing thirty-foot climbing wall that was once the factory’s ore wall.
3. Fort Sheridan Forest Preserve
One of the more picturesque views of Lake Michigan can be found here, a forty five–minute drive north of downtown Chicago on the site of a former army post. The lake stretches majestically over Fort Sheridan’s 70-foot-high bluff; hike down to enjoy the sandy white beach, or head away from the lake and stroll through three-plus miles of forest and pristine bird-watching trails.
4. Gillson Park
800 Gillson Park Dr., Wilmette
Beachgoers in Chicago aren’t expecting Maui or Playa del Carmen. But Gillson Beach, within Gillson Park in Wilmette, comes close to achieving a tropical ideal. With immaculate soft white sand and a recently renovated beach house, Gillson Beach—calm, clean, spacious—feels someplace far from the hubbub of the city. It’s also next to the Baháʼí House of Worship; even the sight of the temple from a distance lowers blood pressure.
5. Captain Daniel Wright Woods
There’s no bad time to visit here, located forty-five minutes north of Chicago, but the most charming season is autumn. The maple and oak trees in this 750-acre forest turn technicolor, as if the fall foliage was cranked to full saturation. Strolling along this three-mile loop, you may share a path with bicyclists and horseback riders alike. After your hike, it’s a short drive to Long Grove, a village famous for its apple cider donuts.
Gyms and Spas
6. Chicago Bath House
This Wicker Park bathhouse has been unabashedly unhip since 1906. A favorite of Russians and Eastern Europeans, you’ll find burly hirsute men and grandmotherly types parading carefree around the premises. There’s usually a serene look to their faces, having been harshly exfoliated or gently beaten by oak and eucalyptus branches. The on-site restaurant caps the sauna experience with cheese blintzes and thick borscht.
7. Aire Ancient Baths Chicago
High on luxury touches (and price tag), the Spanish spa chain Aire has converted a turn-of-the-century paint factory into the city’s preeminent temple for pampering. There’s coed soaking pools and steam rooms as expected, but the draw here is the aesthetic: exposed bricks, high ceilings, candlelight, and lanterns, as if you’re bathing in an underground spring in the year 500 AD. For an extra fee, you can even soak in a tub filled with red wine.
8. First Ascent
3516 N. Spaulding Ave., Chicago
(plus other locations)
A decade ago, four Chicago climbing enthusiasts opened a gym in the Avondale neighborhood to proselytize the sport of indoor climbing. Today, First Ascent is a mini-Midwest empire, with six locations in Illinois and an outpost in Pittsburgh. But its flagship Avondale gym remains the most thrilling to visit. There’s 26,000 square feet of terrain reaching sixty feet high, with group classes and personal training to suit your climbing experience.
Food and Fuel
9. BiXi Beer
2515 N. Milwaukee Ave., Chicago
An Asian brewpub with no peer in Chicago: A house-brewed German Kolsch with green tea blossoms, sandwich buns made from Japanese milk bread, a Scotch egg with Thai flavors. Its singular dim sum brunch is reason enough to visit on weekends (see: Chicago Italian beef baos).
10. Hopleaf Bar
Hopleaf is to beer nerds what the Pantheon is to Rome tourists: Folks travel great distances to pay their respects. Here, you’ll find nearly 200 beers—from the obscure to the extra-obscure—along with fortifying fare like mussels and sausage platters.
11. Bungalow by Middle Brow
2840 W. Armitage Ave., Chicago
Does it make its own natural wine? Brew its own IPA? Bake fantastic sourdough loaves and pastries? Serve Chicago’s most beloved pizza? Bungalow by Middle Brow is the captain of the football team who’s also a straight-A student and first-chair concert violinist: You’re wowed by how it’s great at so many things.
12. Cabra
Perched on the rooftop of The Hoxton hotel is chef Stephanie Izard’s Peruvian homage and what may be the prettiest restaurant in town. From the ceviches and empanadas on the menu to the sweeping al fresco views of the city, everything at Cabra shouts festive, colorful, and buoyant.
13. Heritage Bikes & Coffee
Half the shop is a bicycle supply and repair shop. The other half is a coffee shop brewing locally roasted beans. Put bikes and coffee together and it’s a real vibe—and a fine one-stop shop if you’re biking through the city.
Where to Stay
14. Hotel Lincoln
Approaching its 100th year, the boutique Hotel Lincoln is situated on prime Chicago real estate: Overlooking the leafy splendors of Lincoln Park, and mere steps from the lake shore. On Wednesdays and Saturdays during warm weather months, the hotel sits across the street from Green City Market, the city’s beloved farmers’ market. From $199
15. St. Regis Hotel
This city doesn’t lack five-star accommodations, but the newly built St. Regis Hotel might be the chicest of all. A 101-story building designed by Jeanne Gang? Proximity to Millennium Park? Restaurants from celebrity chef Evan Funke? Check, check, and check. From $550
16. Nobu Hotel
You’d expect elegant, understated touches in a hotel bearing the name of acclaimed Japanese chef Nobu Matsuhisa. But this hotel has achieved legendary status in certain corners of the Internet: Guests have rapturous praise for its teak soaking tub with city views. There are few pleasures more indulgent than relaxing in a wooden tub while snacking on room service otoro sushi. From $480
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