Cheap flights from Chicago to San José del Cabo from CA $205

View CA $205 flight on Sun, Sep. 28, 2025Opens in a new window

Popular airlines from Chicago to San José del Cabo

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Cheap flights from Chicago (CHI) to San José del Cabo (SJD)

Prices were available within the past 7 days and start at CA $205 for one-way flights and CA $475 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Volaris
Sun, Sep. 28 - Sun, Oct. 5
ORD
Chicago
SJD
San José del Cabo
CA $475 Roundtrip, found 3 days ago
CA $475
Roundtrip
found 3 days ago
Select Volaris flight, departing Sun, Sep. 28 from Chicago to San José del Cabo, returning Sun, Oct. 5, priced at CA $475 found 3 days ago
Volaris
Sun, Sep. 28 - Sun, Oct. 5
ORD
Chicago
SJD
San José del Cabo
CA $480 Roundtrip, found 3 days ago
CA $480
Roundtrip
found 3 days ago
Select Volaris flight, departing Sun, Sep. 28 from Chicago to San José del Cabo, returning Sun, Oct. 5, priced at CA $480 found 3 days ago
American Airlines
Sun, Sep. 28 - Sun, Oct. 5
ORD
Chicago
SJD
San José del Cabo
CA $509 Roundtrip, found 3 days ago
CA $509
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Sep. 28 from Chicago to San José del Cabo, returning Sun, Oct. 5, priced at CA $509 found 3 days ago
Hawaiian Airlines
Tue, Oct. 21 - Tue, Oct. 28
ORD
Chicago
SJD
San José del Cabo
CA $524 Roundtrip, found 2 days ago
CA $524
Roundtrip
found 2 days ago
Select Hawaiian Airlines flight, departing Tue, Oct. 21 from Chicago to San José del Cabo, returning Tue, Oct. 28, priced at CA $524 found 2 days ago
Alaska Airlines
Mon, Oct. 20 - Tue, Oct. 28
ORD
Chicago
SJD
San José del Cabo
CA $532 Roundtrip, found 2 days ago
CA $532
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Mon, Oct. 20 from Chicago to San José del Cabo, returning Tue, Oct. 28, priced at CA $532 found 2 days ago
Delta
Mon, Oct. 20 - Thu, Oct. 30
ORD
Chicago
SJD
San José del Cabo
CA $533 Roundtrip, found 2 days ago
CA $533
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct. 20 from Chicago to San José del Cabo, returning Thu, Oct. 30, priced at CA $533 found 2 days ago

Find the cheapest month to fly from Chicago (CHI) to San José del Cabo (SJD)

September is typically the cheapest month to fly

From CA $453 - CA $712 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.