Cheap flights from Seattle to Historic Route 66

View AU$136 flight on Thu, 28 Aug. 2025Opens in a new window

Popular airlines from Seattle to Historic Route 66

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

  • Hawaiian Airlines

    Hawaiian Airlines

  • 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 Seattle (SEA) 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
Sat, 25 Oct. - Fri, 31 Oct.
SEA
Seattle
ORD
Chicago
AU$283 Return, found 6 days ago
AU$283
Return
found 6 days ago
Select American Airlines flight, departing Sat, 25 Oct. from Seattle to Chicago, returning Fri, 31 Oct., priced at AU$283 found 6 days ago
Delta
Sat, 25 Oct. - Fri, 31 Oct.
SEA
Seattle
ORD
Chicago
AU$283 Return, found 6 days ago
AU$283
Return
found 6 days ago
Select Delta flight, departing Sat, 25 Oct. from Seattle to Chicago, returning Fri, 31 Oct., priced at AU$283 found 6 days ago
Alaska Airlines
Sat, 30 Aug. - Sat, 6 Sep.
SEA
Seattle
ORD
Chicago
AU$285 Return, found 2 days ago
AU$285
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 30 Aug. from Seattle to Chicago, returning Sat, 6 Sep., priced at AU$285 found 2 days ago
Delta
Sat, 30 Aug. - Sat, 6 Sep.
SEA
Seattle
ORD
Chicago
AU$286 Return, found 2 days ago
AU$286
Return
found 2 days ago
Select Delta flight, departing Sat, 30 Aug. from Seattle to Chicago, returning Sat, 6 Sep., priced at AU$286 found 2 days ago
Hawaiian Airlines
Wed, 3 Sep. - Sun, 7 Sep.
SEA
Seattle
ORD
Chicago
AU$312 Return, found 1 day ago
AU$312
Return
found 1 day ago
Select Hawaiian Airlines flight, departing Wed, 3 Sep. from Seattle to Chicago, returning Sun, 7 Sep., priced at AU$312 found 1 day ago
United
Sat, 25 Oct. - Fri, 31 Oct.
SEA
Seattle
ORD
Chicago
AU$353 Return, found 6 days ago
AU$353
Return
found 6 days ago
Select United flight, departing Sat, 25 Oct. from Seattle to Chicago, returning Fri, 31 Oct., priced at AU$353 found 6 days ago

Find the cheapest month to fly from Seattle (SEA) to Chicago (ORD)

November is typically the cheapest month to fly

From AU$148 - AU$534 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.