Cheap flights from Orlando to Historic Route 66

View AU$122 flight on Wed, 17 Sep. 2025Opens in a new window

Popular airlines from Orlando to Historic Route 66

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Orlando (ORL) to Historic Route 66 (CHI)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 5 Dec. - Fri, 12 Dec.
MCO
Orlando
ORD
Chicago
AU$275 Return, found 6 hours ago
AU$275
Return
found 6 hours ago
Select American Airlines flight, departing Fri, 5 Dec. from Orlando to Chicago, returning Fri, 12 Dec., priced at AU$275 found 6 hours ago
American Airlines
Mon, 8 Sep. - Mon, 22 Sep.
MCO
Orlando
ORD
Chicago
AU$276 Return, found 5 days ago
AU$276
Return
found 5 days ago
Select American Airlines flight, departing Mon, 8 Sep. from Orlando to Chicago, returning Mon, 22 Sep., priced at AU$276 found 5 days ago
American Airlines
Fri, 5 Dec. - Fri, 12 Dec.
MCO
Orlando
ORD
Chicago
AU$290 Return, found 6 hours ago
AU$290
Return
found 6 hours ago
Select American Airlines flight, departing Fri, 5 Dec. from Orlando to Chicago, returning Fri, 12 Dec., priced at AU$290 found 6 hours ago
American Airlines
Fri, 5 Dec. - Fri, 12 Dec.
MCO
Orlando
ORD
Chicago
AU$321 Return, found 6 hours ago
AU$321
Return
found 6 hours ago
Select American Airlines flight, departing Fri, 5 Dec. from Orlando to Chicago, returning Fri, 12 Dec., priced at AU$321 found 6 hours ago
United
Mon, 1 Sep. - Mon, 8 Sep.
MCO
Orlando
ORD
Chicago
AU$381 Return, found 6 days ago
AU$381
Return
found 6 days ago
Select United flight, departing Mon, 1 Sep. from Orlando to Chicago, returning Mon, 8 Sep., priced at AU$381 found 6 days ago
Delta
Mon, 1 Sep. - Mon, 8 Sep.
MCO
Orlando
MDW
Chicago
AU$457 Return, found 6 days ago
AU$457
Return
found 6 days ago
Select Delta flight, departing Mon, 1 Sep. from Orlando to Chicago, returning Mon, 8 Sep., priced at AU$457 found 6 days ago

Find the cheapest month to fly from Orlando (ORL) to Chicago (ORD)

February is typically the cheapest month to fly

From AU$106 - AU$511 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.