Bone-chills begone! Chicago’s hottest month is here, and there’s nothing residents enjoy more than the Great Outdoors, which this lake-kissing city boasts in spades. So slap on the sunblock and slip on your finest athleisure ensemble for a day of sprightly, alfresco escapades.
Morning: River Cruisin’
You’re here for Chicago’s showstopping architecture, right? There’s no better way to drink it all in than from the breezy open-top comfort of a CAF river cruiser. Nonprofit Chicago Architecture Foundation’s ‘First Lady’ will take you on an insightful 90-minute chug past more than 50 historic buildings, revealing the city’s 100-year transformation from rustic wallflower to gutsy deco dame.
Lunch: Italian Wonderland
Handily placed between your CAF pick-up/drop-off point and the Peninsula (should you require a quick refresh), 63,000-sq-ft marketplace Eataly is a gloriously full-fat, carbo-load of artisanal Italian eateliers, plus there’s a formaggi counter and molto vino for souvenirs and gifting. For afters, there’s a devilish Nutella bar – although nothing says summer quite like a lickalicious ice-cream treat, and the perma-packed gelato stand on the first floor boasts a rainbow of creamy-dreamy flaves from offbeat olive oil to divine pistachio. Bellissimo!
Afternoon: The Lakefront
Beautiful Lake Michigan is the reason many people live in (and love) Chicago; to leave without visiting would be sacrilege. Cab it to the corner of W Armitage Ave and N Clark St for a delightful amble around Lincoln Park. Entering the park, bear right at N Stockton, then left at N Ridge, which goes over South Pond – don’t forget to admire the downtown views from the mini bridge. Once over, follow the road right (left will take you to the zoo) until you reach N Cannon, then continue up to the overpass. Cross, then head right, toward the city for more pic-perfect downtown vistas. Alternatively shed some of those deep-dish calories with an easy-breezy cycle ride along the waterfront (the exercise-allergic can hop on a zippy Segway). There are four bike/Segway stations between Foster Beach and Millennium Park.
Evening: Cocktail O’Clock
Boy, have you earned a stiffener! Finish your alfresco foray with cocktails and tasty seasonal American nibbles at Danny Meyer’s elegant, contempo bar-resto GreenRiver. This 18th-floor outdoor patio boasts killer outlooks over Lake Michigan and Streeterville’s skyscrapers. Or, for something closer to home, why not slink up to The Pen’s own rouge-hued Shanghai Terrace for dim sum and specialty tipples. Cin cin!
Chicago's First Lady (CAF) / Chicago Riverwalk (look for the blue awning) / N Michigan Ave & E Upper Wacker Dr / +1 312 922 3432 / approx every hr / architecture.org
Eataly / 43 E Ohio St / +1 312 521 8700 / 8am-11pm daily / eataly.com
Lakefront / W Armitage Ave & N Clark St
GreenRiver / 18/F / 259 E Erie St / +1 312 337 0101 / daily / greenriverchi.com
Shanghai Terrace / 4/F / The Peninsula / +1 312 573 6695 / daily / May-Oct / peninsula.com