Cheap flights from Chicago to Central Oregon

View AU$229 flight on Mon, 1 Sep. 2025Opens in a new window

Popular airlines from Chicago to Central Oregon

  • 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 Chicago (CHI) to Central Oregon (RDM)

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.

Alaska Airlines
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$501 Return, found 6 days ago
AU$501
Return
found 6 days ago
Select Alaska Airlines flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$501 found 6 days ago
Alaska Airlines
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$504 Return, found 6 days ago
AU$504
Return
found 6 days ago
Select Alaska Airlines flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$504 found 6 days ago
Alaska Airlines
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$528 Return, found 6 days ago
AU$528
Return
found 6 days ago
Select Alaska Airlines flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$528 found 6 days ago
Alaska Airlines
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$532 Return, found 6 days ago
AU$532
Return
found 6 days ago
Select Alaska Airlines flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$532 found 6 days ago
Alaska Airlines
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$565 Return, found 6 days ago
AU$565
Return
found 6 days ago
Select Alaska Airlines flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$565 found 6 days ago
Delta
Mon, 1 Sep. - Mon, 8 Sep.
ORD
Chicago
RDM
Redmond
AU$573 Return, found 6 days ago
AU$573
Return
found 6 days ago
Select Delta flight, departing Mon, 1 Sep. from Chicago to Redmond, returning Mon, 8 Sep., priced at AU$573 found 6 days ago

Find the cheapest month to fly from Chicago (CHI) to Redmond (RDM)

April is typically the cheapest month to fly

From AU$335 - AU$704 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.