Cheap flights from San Francisco to Historic Route 66

View AU$137 flight on Fri, 31 Oct. 2025Opens in a new window

Popular airlines from San Francisco to Historic Route 66

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

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Cheap Flights from San Francisco (SJC) 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, 6 Sep. - Sat, 13 Sep.
SFO
San Francisco
ORD
Chicago
AU$303 Return, found 4 days ago
AU$303
Return
found 4 days ago
Select American Airlines flight, departing Sat, 6 Sep. from San Francisco to Chicago, returning Sat, 13 Sep., priced at AU$303 found 4 days ago
American Airlines
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$326 Return, found 7 hours ago
AU$326
Return
found 7 hours ago
Select American Airlines flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$326 found 7 hours ago
Alaska Airlines
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$335 Return, found 7 hours ago
AU$335
Return
found 7 hours ago
Select Alaska Airlines flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$335 found 7 hours ago
Delta
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$359 Return, found 7 hours ago
AU$359
Return
found 7 hours ago
Select Delta flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$359 found 7 hours ago
Hawaiian Airlines
Tue, 30 Sep. - Tue, 7 Oct.
SFO
San Francisco
ORD
Chicago
AU$375 Return, found 4 days ago
AU$375
Return
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, 30 Sep. from San Francisco to Chicago, returning Tue, 7 Oct., priced at AU$375 found 4 days ago
United
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$382 Return, found 7 hours ago
AU$382
Return
found 7 hours ago
Select United flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$382 found 7 hours ago

Find the cheapest month to fly from San Francisco (SFO) to Chicago (ORD)

September is typically the cheapest month to fly

From AU$161 - AU$317 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.