Sarasota to Chicago train

A culturally-rich alternative to the nearby theme parks of Orlando, Sarasota's Gulf Coast location is hard to resist. It became the winter base for many well-to-do families in the early twentieth century, during which time much of the town developed a subtle Italian feel.

Not only is the climate similar to what you might experience in southern Italy, but many of Sarasota's buildings were constructed to resemble the country's renaissance masterworks too. A good example is the Ringling family's Ca' d'Zan Venetian-style mansion.

The Ringlings made their money from circuses before giving their name to the much-celebrated John and Mable Ringling Museum of Art. It contains 21 galleries of European paintings, archaeological artifacts, and American art totaling 10,000 objects.

With weather so fine, you'll probably be looking with more than half an eye at Sarasota's numerous excellent resorts and beaches, many of which lie on a group of keys within the city limits. Bonus: our research ranked Sarasota as the #3 cheapest Spring Break destination, so you can soak up the sun on the cheap.

Arriving in Sarasota is equally easy thanks to its Cattleman Transfer Centre and Fruitville Road bus stations. Between them, travelers can connect by bus everywhere from Tampa to Tucson. Amtrak also operates a Thruway bus service from the defunct Sarasota rail station to Tampa for onward connections by train on the Silver Service. This service runs between Miami and New York City via Washington, D.C.

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.