Cheap flights from Denver to Historic Route 66

View AU$106 flight on Tue, 30 Dec. 2025Opens in a new window

Popular airlines from Denver 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 Denver (DEN) 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
Thu, 23 Oct. - Wed, 29 Oct.
DEN
Denver
ORD
Chicago
AU$232 Return, found 3 days ago
AU$232
Return
found 3 days ago
Select American Airlines flight, departing Thu, 23 Oct. from Denver to Chicago, returning Wed, 29 Oct., priced at AU$232 found 3 days ago
American Airlines
Thu, 18 Sep. - Sat, 20 Sep.
DEN
Denver
ORD
Chicago
AU$270 Return, found 3 hours ago
AU$270
Return
found 3 hours ago
Select American Airlines flight, departing Thu, 18 Sep. from Denver to Chicago, returning Sat, 20 Sep., priced at AU$270 found 3 hours ago
American Airlines
Sat, 16 Aug. - Mon, 18 Aug.
DEN
Denver
ORD
Chicago
AU$286 Return, found 3 days ago
AU$286
Return
found 3 days ago
Select American Airlines flight, departing Sat, 16 Aug. from Denver to Chicago, returning Mon, 18 Aug., priced at AU$286 found 3 days ago
Delta
Sat, 27 Sep. - Tue, 30 Sep.
DEN
Denver
ORD
Chicago
AU$333 Return, found 4 days ago
AU$333
Return
found 4 days ago
Select Delta flight, departing Sat, 27 Sep. from Denver to Chicago, returning Tue, 30 Sep., priced at AU$333 found 4 days ago
United
Thu, 23 Oct. - Wed, 29 Oct.
DEN
Denver
ORD
Chicago
AU$337 Return, found 3 days ago
AU$337
Return
found 3 days ago
Select United flight, departing Thu, 23 Oct. from Denver to Chicago, returning Wed, 29 Oct., priced at AU$337 found 3 days ago
Alaska Airlines
Thu, 23 Oct. - Wed, 29 Oct.
DEN
Denver
ORD
Chicago
AU$450 Return, found 3 days ago
AU$450
Return
found 3 days ago
Select Alaska Airlines flight, departing Thu, 23 Oct. from Denver to Chicago, returning Wed, 29 Oct., priced at AU$450 found 3 days ago

Find the cheapest month to fly from Denver (DEN) to Chicago (ORD)

September is typically the cheapest month to fly

From AU$74 - AU$187 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.