How much is a ticket from Orlando International to Chicago Midway?

Flight prices from Orlando to Chicago change depending on demand and time of booking.

$56 is the best price recorded in the last 15 days.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Which departure and arrival airports are available?

Between Orlando and Chicago, flight options may depend on the combination of airports available.

• Airports in Orlando: Orlando is connected by 2 airports - Executive, Sanford.
• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Adjust your flight filters for Orlando International – Chicago Midway

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to United States? These cities are popular too: Atlanta, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.