Cheap flights from Orlando to Chicago

One-way fares from $46 · ORL → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Orlando
Cheapest fare
$46

Allegiant Air · Thu, Jan 14

Cheapest month
January

from $46

Direct flights
Yes

Allegiant Air, Frontier Airlines and American Airlines

Flight time
2h 48m

1,590 km

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Cheapest month to fly from Orlando to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 $82
  2. December 2026 $116
  3. January 2027 Cheapest $46
  4. March 2027 $105
  5. June 2027 $181

Cheapest dates in January 2027

The lowest fares we've seen for each day, cheapest first.

Allegiant Air
Depart13:56 Thu, Jan 14SFB → RFD 2h 55m · Direct
$46one way, per person
View deal
See every date in January 2027 →

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Getting around

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About flights from Orlando to Chicago

Orlando (ORL) and Chicago (CHI) are about 1,590 km apart. Direct flights take around 2h 48m, and recent direct fares were with Allegiant Air, Frontier Airlines and American Airlines. Over the next few months, one-way fares start from $46, and January 2027 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Orlando to Chicago?

The cheapest one-way fare we've seen recently is $46 with Allegiant Air, departing Thursday, January 14, 2027. Over the coming months, the lowest fare in each month ranges from $46 to $181.

What is the cheapest month to fly from Orlando to Chicago?

January 2027 currently has the lowest fares, from $46 one way.

Are there direct flights from Orlando to Chicago?

Yes. Recent direct fares were with Allegiant Air, Frontier Airlines and American Airlines.

How long is the flight from Orlando to Chicago?

A direct flight takes about 2h 48m. Orlando and Chicago are around 1,590 km apart.

Which airlines fly from Orlando to Chicago?

Recent fares on this route were with Allegiant Air, Frontier Airlines and American Airlines.

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