Fair warning: This will ruin you for all other forms of air travel. If you aren’t already among the fortunate few (read: P&G executives) to experience Ultimate Air Shuttle, consider this endorsement an excuse to indulge a little. It’s an admittedly high price point ($499 round trip), but you really do get what you pay for. Departures to Chicago (one of the five Ultimate Air destinations) leave from Lunken Airport weekdays at 8:55 a.m.; the flights are direct charter service, pre-screened (meaning no TSA security checks), with free parking, snacks, and drinks and no baggage fees. You can even show up as late as 15 minutes (!) before takeoff. It’s the closest thing to a private jet for those of us not named Beyoncé.
Arrange for the complimentary shuttle service at Midway Airport to drop you at the train and head into the city for a stay at the ACME Hotel in the River North neighborhood. The place has a funky, artsy aesthetic—and suites with wireless sound systems—and is supremely located and a nice change of pace from standard hotel sterility. Take a stroll along the Magnificent Mile to a modern Italian dinner at Spiaggia Restaurant, home to Top Chef–winning Joe Flamm, then head to the Second City comedy club for a post-meal chuckle.
When in Chicago, you gotta go to Wrigley Field. Even if you’re not up for a game—or the Cubbies aren’t in town—daily tours offer a behind-the-scenes look at the “friendly confines,” including a walk on the field. If the weather won’t cooperate or baseball just isn’t your bag, swing by the Art Institute of Chicago to check out Picasso’s The Old Guitarist, Wood’s American Gothic, and more than 90,000 works of art in the museum’s permanent collection.
And because Ultimate Air’s weekday return flights depart from Midway at 5:15 p.m., you’ll be home in time to make dinner and catch Jeopardy. Just like Beyoncé.
Ultimate Air Shuttle, $499, ultimateairshuttle.com
ACME Hotel Company, $250–$350/night, acmehotelcompany.com
Spiaggia Restaurant, $18–$245, spiaggiarestaurant.com