Cheap flights from Madrid to Historic Route 66

View AU$473 flight on Thu, 20 Nov. 2025Opens in a new window

Popular airlines from Madrid to Historic Route 66

  • American Airlines

    American Airlines

  • Air Canada

    Air Canada

  • Finnair

    Finnair

  • ITA Airways

    ITA Airways

  • British Airways

    British Airways

  • Delta

    Delta

  • Aer Lingus

    Aer Lingus

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Cheap Flights from Madrid (MAD) 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.

Air Canada
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
ORD
Chicago
AU$1,382 Return, found 8 hours ago
AU$1,382
Return
found 8 hours ago
Select Air Canada flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,382 found 8 hours ago
United
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
ORD
Chicago
AU$1,412 Return, found 8 hours ago
AU$1,412
Return
found 8 hours ago
Select United flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,412 found 8 hours ago
United
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
ORD
Chicago
AU$1,418 Return, found 8 hours ago
AU$1,418
Return
found 8 hours ago
Select United flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,418 found 8 hours ago
KLM
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
MDW
Chicago
AU$1,605 Return, found 8 hours ago
AU$1,605
Return
found 8 hours ago
Select KLM flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,605 found 8 hours ago
Aer Lingus
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
ORD
Chicago
AU$1,809 Return, found 8 hours ago
AU$1,809
Return
found 8 hours ago
Select Aer Lingus flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,809 found 8 hours ago
Virgin Atlantic
Sun, 10 Aug. - Sun, 31 Aug.
MAD
Madrid
MDW
Chicago
AU$1,837 Return, found 8 hours ago
AU$1,837
Return
found 8 hours ago
Select Virgin Atlantic flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,837 found 8 hours ago

Find the cheapest month to fly from Madrid (MAD) to Chicago (ORD)

January is typically the cheapest month to fly

From AU$563 - AU$1,727 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.