Cheap flights from Orlando to Northwest Chicago

View AU$119 flight on Tue, 30 Sep. 2025Opens in a new window

Popular airlines from Orlando to Northwest Chicago

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

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Cheap Flights from Orlando (ORL) to Northwest Chicago (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
Tue, 9 Sep. - Tue, 16 Sep.
MCO
Orlando
ORD
Chicago
AU$238 Return, found 1 day ago
AU$238
Return
found 1 day ago
Select American Airlines flight, departing Tue, 9 Sep. from Orlando to Chicago, returning Tue, 16 Sep., priced at AU$238 found 1 day ago
American Airlines
Fri, 5 Dec. - Fri, 12 Dec.
MCO
Orlando
ORD
Chicago
AU$275 Return, found 3 days ago
AU$275
Return
found 3 days ago
Select American Airlines flight, departing Fri, 5 Dec. from Orlando to Chicago, returning Fri, 12 Dec., priced at AU$275 found 3 days ago
American Airlines
Fri, 15 Aug. - Sun, 17 Aug.
MCO
Orlando
ORD
Chicago
AU$288 Return, found 2 days ago
AU$288
Return
found 2 days ago
Select American Airlines flight, departing Fri, 15 Aug. from Orlando to Chicago, returning Sun, 17 Aug., priced at AU$288 found 2 days ago
American Airlines
Fri, 5 Dec. - Fri, 12 Dec.
MCO
Orlando
ORD
Chicago
AU$290 Return, found 3 days ago
AU$290
Return
found 3 days ago
Select American Airlines flight, departing Fri, 5 Dec. from Orlando to Chicago, returning Fri, 12 Dec., priced at AU$290 found 3 days ago
Delta
Tue, 9 Sep. - Tue, 16 Sep.
MCO
Orlando
MDW
Chicago
AU$299 Return, found 1 day ago
AU$299
Return
found 1 day ago
Select Delta flight, departing Tue, 9 Sep. from Orlando to Chicago, returning Tue, 16 Sep., priced at AU$299 found 1 day ago
United
Tue, 9 Sep. - Tue, 16 Sep.
MCO
Orlando
ORD
Chicago
AU$322 Return, found 1 day ago
AU$322
Return
found 1 day ago
Select United flight, departing Tue, 9 Sep. from Orlando to Chicago, returning Tue, 16 Sep., priced at AU$322 found 1 day 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.