Cheap flights from Orlando to Chicago
Fares from $76 in March 2027. Compare every month below, then book with the site you like.
Search Orlando → Chicago flightsCheapest Orlando to Chicago fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- November 2026Nov 4 · one way · Frontier · Direct$116See deal
- December 2026Dec 30 · one way · Frontier · Direct$120See deal
- January 2027Jan 14 · one way · Frontier · 1 stop$80See deal
- February 2027Feb 16 · one way · Frontier · Direct$91See deal
- March 2027Mar 3 · one way · Frontier · 1 stop$76See deal
- June 2027Jun 30 · one way · American Airlines · Direct$181See deal
Orlando to Chicago at a glance
- Distance1,007 miles
- Nonstop flight timeabout 2h 45m
- Cheapest monthMarch 2027
- Airport codesMCO → CHI
Plan your Chicago trip
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Frequently asked questions
- How much is a flight from Orlando to Chicago?
- The cheapest fare we found recently is $76 per person, departing Mar 3 on Frontier. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from Orlando to Chicago?
- March 2027 is currently the cheapest month, from $76. June 2027 is the most expensive, from $181.
- Are there direct flights from Orlando to Chicago?
- Yes. Recent searches found nonstop fares from $91.
- Which airlines fly from Orlando to Chicago?
- The cheapest recent fares on this route were on Frontier, American Airlines.
- How long is the flight from Orlando to Chicago?
- Orlando and Chicago are about 1,007 miles apart, so a nonstop flight takes roughly 2h 45m. Flights with a stop take longer, depending on the connection.
- How do I find the cheapest flight from Orlando to Chicago?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
More flights from Orlando
- Orlando to New York
- Orlando to Los Angeles
- Orlando to Miami
- Orlando to Las Vegas
- Orlando to San Francisco
- Orlando to Washington, D.C.
- Orlando to Boston
- Orlando to Atlanta
- Orlando to Dallas
- Orlando to Houston
- Orlando to Seattle
- Orlando to Denver