Chicago in Style

Chicago in Style

t hits you unexpectedly, the desire to pop down to Chicago to enjoy a show, do a little shopping or dine at a favorite restaurant. But just as quickly you brush off the idea, citing the long drive and potential traffic issues and parking hassles. What if getting to Chicago were enjoyable? What if the transportation were part of the fun? Intrigued by this notion, we test-drove two luxe ways to travel to the Windy City.

The Experience: A sleek black AJ Prestige limousine arrived at 8:55 a.m. to chauffeur us on a daytrip to downtown Chicago. We quickly settled into the cushy leather seats of the eight-passenger Lincoln. I like to think we looked out our tinted windows to other travelers combating traffic. In reality, we were too busy having a good time—lounging, laughing and literally enjoying the ride. In fact, we wouldn’t have minded if a traffic jam had delayed us awhile.

By 11:25 a.m. we were making our way down Michigan Avenue. Our driver dropped us off for lunch, and we simply called him when we were ready to head home. Back inside the cozy limo we sprawled out on the seats and napped (you can also bring DVDs to watch on the built-in television or a bottle of champagne to toast the excursion). Before we knew it we were back in Madison.

Bottom Line: Traveling by limo is not only luxurious and hassle-free, it’s also the most comfortable way to make the trip. The travel experience starts from the moment the vehicle arrives, making it a great choice for a romantic date or a day trip with friends. AJ Prestige can customize packages to suit whatever you want to do in the city and whenever you want to go.

Details: The company prices its services by the hour and on a flat rate for one-way trips. Round-trip transportation to Chicago costs roughly $90 an hour during the weekdays and $100 an hour on weekends, plus a twenty percent gratuity and five percent sales tax. However, the hourly rate typically drops the longer a customer rents a limousine.

AJ Prestige Limousine, 338-5800,

The Experience: Within minutes of arriving at Wisconsin Aviation, we strode out on the tarmac and climbed into a sporty, four-seat Cirrus SR22 Turbo. The pilot handed out headphones that would cancel noise emitted from the single-engine plane and allow us to talk to one another. Our 10:15 a.m. takeoff was quick and smooth and soon we were cruising at 3,500 feet over a patchwork quilt of fields, lakes, forests and roads. The pilot mentioned that the view is even more spectacular at night, when a network of lights spreads out in every direction.

All of a sudden, a silhouette of the Chicago skyline appeared in the distance. Minutes later we soared over Lake Michigan and next to the city’s downtown skyscrapers. Hundreds of airports, such as Chicago’s O’Hare, service commercial aircraft, yet thousands around the country accommodate smaller planes and jets. We landed at the Bolingbrook airport just south of the city, but roughly a dozen options exist (you may have to take a cab to reach your downtown destination). Back on the plane, our trip back to Madison took a mere thirty-six minutes.

Bottom Line: Chartering a plane is the most efficient—and exhilarating—means of transportation. It’s ideal if you want to get to Chicago quickly for a game or concert, or if you want to sweep a date off his or her feet. Wisconsin Aviation maintains a large charter fleet, from single-engine, three-passenger planes to nine-passenger jets.

Details: Chartering the Cirrus SR22 is $500 an hour, including a pilot. Prices vary based on the size and type of plane rented, destination and duration of the charter.

Wisconsin Aviation, 268-5000 or (888) 405-0211,

Katie Vaughn is associate editor of Madison Magazine.