Cheap train tickets from Orlando to Chicago

Orlando is the Theme Park Capital of the World, thanks to the high density of thrilling parks like Walt Disney World, Universal Studios, SeaWorld, LEGOLAND, Gatorland and more. It's no wonder we rated Orlando the #1 travel destination for families. Family holiday or not, if the highlight of your trip is picking out a wand at Ollivanders in the Wizarding World of Harry Potter or finally meeting Elsa in the Magic Kingdom, you know we won't judge.

Winter Park and Thornton Park – not more theme parks, we promise – are trendy neighbourhoods where you can experience some of Orlando's world-class shopping, dining, and craft beer. You can also immerse yourself in some of Florida's unique wildlife at Orlando Wetlands Park, or the more central Lake Eola Park downtown. Orlando enjoys an average of 233 days of sunshine a year, so even though it's one of the cheapest cities to visit over Spring Break, you'll soak up that sweet, sweet sun almost any time of year.

Craving the ocean? Head a few hours outside Orlando for some of Florida's gorgeous beaches like New Smyrna Beach, Cocoa Beach, and the Canaveral National Seashore. Two large airports, as well as many coach and train companies with service in the area, mean that travelling from Orlando to other sunny Florida destinations and beyond is a breeze.

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 holiday 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 neighbourhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theatre, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transport 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 coach and train stations throughout the city, getting to the Windy City is a breeze.