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

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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 3 days ago
AU$1,382
Return
found 3 days ago
Select Air Canada flight, departing Sun, 10 Aug. from Madrid to Chicago, returning Sun, 31 Aug., priced at AU$1,382 found 3 days ago
Delta
Thu, 31 Jul. - Sun, 3 Aug.
MAD
Madrid
ORD
Chicago
AU$1,417 Return, found 2 days ago
AU$1,417
Return
found 2 days ago
Select Delta flight, departing Thu, 31 Jul. from Madrid to Chicago, returning Sun, 3 Aug., priced at AU$1,417 found 2 days ago
Delta
Thu, 31 Jul. - Sun, 3 Aug.
MAD
Madrid
MDW
Chicago
AU$1,425 Return, found 2 days ago
AU$1,425
Return
found 2 days ago
Select Delta flight, departing Thu, 31 Jul. from Madrid to Chicago, returning Sun, 3 Aug., priced at AU$1,425 found 2 days ago
TAP Portugal
Thu, 31 Jul. - Sun, 3 Aug.
MAD
Madrid
ORD
Chicago
AU$1,703 Return, found 2 days ago
AU$1,703
Return
found 2 days ago
Select TAP Portugal flight, departing Thu, 31 Jul. from Madrid to Chicago, returning Sun, 3 Aug., priced at AU$1,703 found 2 days ago
KLM
Thu, 31 Jul. - Sun, 3 Aug.
MAD
Madrid
ORD
Chicago
AU$1,704 Return, found 2 days ago
AU$1,704
Return
found 2 days ago
Select KLM flight, departing Thu, 31 Jul. from Madrid to Chicago, returning Sun, 3 Aug., priced at AU$1,704 found 2 days ago
United
Fri, 1 Aug. - Fri, 8 Aug.
MAD
Madrid
ORD
Chicago
AU$1,752 Return, found 2 days ago
AU$1,752
Return
found 2 days ago
Select United flight, departing Fri, 1 Aug. from Madrid to Chicago, returning Fri, 8 Aug., priced at AU$1,752 found 2 days 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.