Cheap flights from Houston to Historic Route 66

View AU$121 flight on Wed, 20 Aug. 2025Opens in a new window

Popular airlines from Houston to Historic Route 66

  • American Airlines

    American Airlines

  • Delta

    Delta

  • United

    United

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Cheap Flights from Houston (HOU) 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
Mon, 22 Sep. - Sat, 27 Sep.
IAH
Houston
ORD
Chicago
AU$242 Return, found 1 day ago
AU$242
Return
found 1 day ago
Select American Airlines flight, departing Mon, 22 Sep. from Houston to Chicago, returning Sat, 27 Sep., priced at AU$242 found 1 day ago
American Airlines
Mon, 22 Sep. - Sat, 27 Sep.
IAH
Houston
ORD
Chicago
AU$272 Return, found 1 day ago
AU$272
Return
found 1 day ago
Select American Airlines flight, departing Mon, 22 Sep. from Houston to Chicago, returning Sat, 27 Sep., priced at AU$272 found 1 day ago
American Airlines
Thu, 11 Sep. - Thu, 18 Sep.
IAH
Houston
ORD
Chicago
AU$298 Return, found 22 hours ago
AU$298
Return
found 22 hours ago
Select American Airlines flight, departing Thu, 11 Sep. from Houston to Chicago, returning Thu, 18 Sep., priced at AU$298 found 22 hours ago
Delta
Mon, 22 Sep. - Sat, 27 Sep.
IAH
Houston
ORD
Chicago
AU$333 Return, found 1 day ago
AU$333
Return
found 1 day ago
Select Delta flight, departing Mon, 22 Sep. from Houston to Chicago, returning Sat, 27 Sep., priced at AU$333 found 1 day ago
United
Mon, 22 Sep. - Sat, 27 Sep.
IAH
Houston
ORD
Chicago
AU$342 Return, found 1 day ago
AU$342
Return
found 1 day ago
Select United flight, departing Mon, 22 Sep. from Houston to Chicago, returning Sat, 27 Sep., priced at AU$342 found 1 day ago
Alaska Airlines
Thu, 14 Aug. - Mon, 18 Aug.
IAH
Houston
STL
St. Louis
AU$985 Return, found 3 days ago
AU$985
Return
found 3 days ago
Select Alaska Airlines flight, departing Thu, 14 Aug. from Houston to St. Louis, returning Mon, 18 Aug., priced at AU$985 found 3 days ago

Find the cheapest month to fly from Houston (HOU) to Chicago (ORD)

January is typically the cheapest month to fly

From AU$77 - AU$609 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.