Sep 23, 2024 · WASHINGTON – Amtrak customers can now purchase tickets on the Floridian, a new temporary route offering a direct round-trip between Chicago and Miami with intermediate stops in Cleveland, Pittsburgh, Washington, D.C., Jacksonville, Orlando, and Tampa that will take customers to these cities in comfort and style.

4 days ago · The latter train was the last winter-seasonal Midwest-Florida train on any route; it lasted until April 30, 1955. Through sleeping cars were operated between a number of Midwestern points and Florida, including Chicago, Detroit, Cleveland, and Buffalo.

From the grandeur of Grant Park’s Buckingham Fountain to iconic museums and skyscrapers, see for yourself why Chicago was once dubbed “Paris on the Prairie.” Engage in retail therapy on the Magnificent Mile or root for the home team within the friendly confines of famed Wrigley Field.

Looking for cheap flights from Chicago to Florida, or a last-minute trip? Find the lowest prices on one-way and round-trip flights right here.

The cheapest ticket to Florida from Chicago found in the last 72 hours was $24 one-way, and $36 round-trip. The most popular route is from Chicago to West Palm Beach , and the cheapest round-trip airline ticket found on this route in the last 72 hours was $44.

Find United Airlines cheap flights from Chicago to Orlando. Enjoy a Chicago to Orlando modern flight experience in premium cabins with Wi-Fi.

There are 11 ways to get from Chicago to Florida by plane, bus, train (Amtrak), or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Find flights to Florida from $26. Fly from Chicago O'Hare Airport on Frontier, Spirit Airlines and more. Search for Florida flights on KAYAK now to find the best deal.

Fly one-way from Chicago (Midway) to Destin/Fort Walton Beach starting at $172. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Fly from Chicago Midway Airport to Florida on Frontier from $39... Search for Florida flights on KAYAK now to find the best deal.