$28 Cheap flight deals from Chicago (CHI) to Kissimmee (ORL)

Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for Chicago to Kissimmee flights at low cost, you will not be disappointed.

Cruising for a bargain deal

Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from Chicago to Kissimmee so you can reach your destination with more money in your pocket to spend.

Cheap Chicago to Kissimmee flights that lead to rewards

Get rewarded for your cheap Chicago to Kissimmee flights by earning miles and points for your airline loyalty or frequent flyer program. Rack up the miles by flying cheaply with Orbitz so you can earn free flights and other savings with your favorite airlines. Just enter your frequent flyer number when booking your discount fare on flights from Chicago to Kissimmee on Orbtiz.com.

Quality combinations

If you require budget Chicago to Kissimmee flights and a bargain hotel to go with it, Orbitz will wow you with the great combinations we can offer. The quality is always high and always a superb value.

Even last minute bookings on our apps

You do not need to be tied to your desktop computer to make your booking. With our cutting-edge mobile tools, you can search for those low cost deals anywhere, anytime. Our app gives you the freedom to secure flights from Chicago to Kissimmee at the very last minute from your mobile device.