Flights from Orlando to Chicago
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Lowest one-way fare
$80
Departing Thu, Jan 14, 2027
See flights on Jan 14Prices last checked Nov 5, 2026
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Cheapest days to fly Orlando to Chicago
The lowest one-way fare found for each day over the next few months.
Cheapest dates found
Good to know: Orlando to Chicago
Nonstop flights, stops and airlines on the cheapest fares we found.
- Nonstop flightsFrom $110Frontier Airlines · Orlando to Chicago Midway · 3h 1m
- Stops on the cheapest faresMostly one stopOf the 2 cheapest fares: 2 one stop.
- Airlines on the cheapest faresFrontier AirlinesFares with stops may combine airlines.
- Airports usedO'Hare and Chicago MidwayWhere the cheapest fares to Chicago arrive, most common first.
Based on the 2 cheapest one-way fares in recent searches, checked Nov 5, 2026.
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Frequently asked questions
How much do flights from Orlando to Chicago cost?
One-way fares start from $80, based on recent searches checked on Nov 5, 2026. Prices change often, so confirm the final fare on our partner's site before booking.
What is the cheapest date to fly from Orlando to Chicago?
The lowest recent one-way fare we found departs on Thu, Jan 14, 2027. Try nearby dates too, since fares can differ by the day.
What is the cheapest month to fly from Orlando to Chicago?
Of the next 3 months, January has the lowest fare we've seen: $80 on Thu, Jan 14, 2027. For comparison, November from $145 and December from $84.
Are there direct flights from Orlando to Chicago?
Yes. The cheapest nonstop fare we found was $110 with Frontier Airlines, from Orlando International Airport to Chicago Midway International Airport, a flight of about 3h 1m.
Which airlines fly from Orlando to Chicago?
The cheapest fares we found were on Frontier Airlines. Fares with stops may combine more than one airline, so check each flight before you book.
Do you sell plane tickets?
No. We compare fares and send you to our travel partner Aviasales, where you choose a booking option and pay. Changes, refunds and support are handled by the airline or agency you book with.