Cheap flights from Oakland to Northwest Chicago

View AU$151 flight on Wed, 15 Oct. 2025Opens in a new window

Popular airlines from Oakland to Northwest Chicago

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Oakland (SJC) to Northwest Chicago (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
Wed, 15 Oct. - Sat, 25 Oct.
SFO
San Francisco
ORD
Chicago
AU$300 Return, found 1 hour ago
AU$300
Return
found 1 hour ago
Select American Airlines flight, departing Wed, 15 Oct. from San Francisco to Chicago, returning Sat, 25 Oct., priced at AU$300 found 1 hour ago
American Airlines
Sat, 6 Sep. - Sat, 13 Sep.
SFO
San Francisco
ORD
Chicago
AU$303 Return, found 5 days ago
AU$303
Return
found 5 days ago
Select American Airlines flight, departing Sat, 6 Sep. from San Francisco to Chicago, returning Sat, 13 Sep., priced at AU$303 found 5 days ago
Alaska Airlines
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$335 Return, found 1 day ago
AU$335
Return
found 1 day ago
Select Alaska Airlines flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$335 found 1 day ago
Hawaiian Airlines
Tue, 28 Oct. - Tue, 11 Nov.
SFO
San Francisco
ORD
Chicago
AU$335 Return, found 1 hour ago
AU$335
Return
found 1 hour ago
Select Hawaiian Airlines flight, departing Tue, 28 Oct. from San Francisco to Chicago, returning Tue, 11 Nov., priced at AU$335 found 1 hour ago
Delta
Tue, 7 Oct. - Tue, 14 Oct.
SFO
San Francisco
ORD
Chicago
AU$359 Return, found 1 day ago
AU$359
Return
found 1 day ago
Select Delta flight, departing Tue, 7 Oct. from San Francisco to Chicago, returning Tue, 14 Oct., priced at AU$359 found 1 day ago
United
Sat, 30 Aug. - Sun, 31 Aug.
SFO
San Francisco
ORD
Chicago
AU$409 Return, found 3 days ago
AU$409
Return
found 3 days ago
Select United flight, departing Sat, 30 Aug. from San Francisco to Chicago, returning Sun, 31 Aug., priced at AU$409 found 3 days ago

Find the cheapest month to fly from Oakland (OAK) to Chicago (ORD)

January is typically the cheapest month to fly

From AU$153 - AU$536 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.