Find cheap flights from Chicago to Kissimmee - Compare and Save

When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Kissimmee does not have its own airport so you’ll be flying into nearby Orlando airport, which is 11.0 mi away.

Direct flights cover the 994 miles separating Chicago and Kissimmee in about 2h 30m.

99 direct flights run between Chicago and Kissimmee on a daily basis. On average, there are about 694 departures each week.

Consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kissimmee.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kissimmee with an airline and back to Chicago with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kissimmee from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

In the last 5 days, the cheapest one-way ticket between Chicago and Kissimmee found on KAYAK was with Frontier for $41. Frontier offered a round-trip connection from $64 and Delta from $111.