Chicago has its luxurious elements — like the striking buildings along the lakefront or the high-end shopping on the renowned Magnificent Mile. Right off famed Michigan Avenue, the city offers another gem, Four Seasons Hotel Chicago. The Forbes Travel Guide Five-Star hotel features unparalleled comfort, world-class dining and a Four-Star spa. So, when the sumptuousness of this Windy City wonder is combined with the powerful elegance of Porsche, you get a partnership that’s hard to beat.
Thankfully, this dream collaboration is a reality for a short time thanks to Porsche Destination Drives, an opportunity where guests at certain Five-Star hotels around the country are offered complimentary two-hour rides in one of the brand’s incomparable vehicles, including the plug-in Panamera S E-Hybrid, 911 Carrera S Cabriolet sports car and Cayenne GTS sport utility vehicle. Participating hotels include Four Seasons Hotel Chicago (through July 12); The Grand Del Mar in San Diego (July 26 to August 23); Mandarin Oriental, San Francisco (September 13 to October 11); and The Canyon Suites at The Phoenician in Scottsdale (November 1 to December 13).
The concierge at the Four Seasons created some driving itineraries, so feel free to use those. But as a Chicago native who’s lived here most of my life, I can take you on a ride through the many moods of Chicago — as well as circle one of my favorite places in the universe, Wrigley Field.
Start out by going north on Lake Shore Drive, one of the city’s — if not the country’s — most iconic drives. Gorgeous Lake Michigan will be on your right as well as some of the city’s fittest people showing off their lithe physiques near the water. Music is as important as a good pair of shades here, so bring your favorite tunes as well as a USB cord to connect to the Porsche’s amazing Bose surround sound system.
Lake Shore Drive ends after a glorious six-mile stretch, so continue heading north along Sheridan Road, past burgeoning Loyola University. After three miles, you’ll pass the lake on your right and then you’re in lovely Evanston. Stay on enchanting Sheridan Road and, before too long, you’ll pass actors Joan and John Cusack’s childhood home on your left. It’s across the street from a large park. At the northern end of Evanston is the beautiful Bahá’í House of Worship, a white structure of Portland cement that is called one of the Seven Wonders of Illinois.
Continue north through the leafy suburbs of Wilmette and Winnetka, as Sheridan’s gentle curves and elegant homes provide a perfect environment for you to get a feel for the Porsche’s smooth handling. (You can’t exactly open it up and go 150 miles per hour, but you can sample some of the powerful acceleration.)
At Lake Cook Road, it’s time to turn back toward Chicago — but you’re not going straight to the hotel. Venture south on Sheridan Road, and make your way back to Lake Shore Drive. You have time for one delicious detour off of Irving Park Road. Go west for a half mile before pulling in to Byron’s Hot Dogs for a classic Chicago dog that’s so good President Obama has had them delivered to the White House. (True Chicago style calls for relish, celery salt, mustard and no ketchup — that’s a cardinal sin in the Second City!) I also highly recommend the fluffy, crispy French fries and the decadently rich chocolate shake.
After you’ve sated yourself on a true local meal, turn left out of the parking lot and go west on Irving Park Road to Clark Street. Turn left again and, in about half a mile, you’ll come to Wrigley Field, a national treasure. You might want to check beforehand that the Cubs aren’t playing at the time; if they are, Wrigleyville is wall-to-wall with baseball fans and the drive will take much longer than the time you’re allotted.
Admire the old-school, utilitarian charm of the ballpark, which houses one of the most storied (and hard-luck) franchises in all of sports. Turn left on Addison and drive along the north side of the stadium, which effortlessly blends in with its urban environs. Take another left on Sheffield Avenue and you’ll pass beneath the famed right-field bleachers, where Sammy Sosa used to routinely hit homers back in the magical summer of 2003. (Just don’t ask how that season ended.) One more left onto Waveland Avenue takes you past the left-field bleachers, an area that is routinely patrolled by ballhawks hoping to catch long home runs.
Turn right on Clark Street to get on Irving Park Road. Then make a right and go one mile to Lake Shore Drive. After the seven-minute trip from Wrigley back to the Four Seasons, consider yourself an enlightened, if not native, Chicagoan.
Photo Courtesy of Cesar Russ Photography