Cheap flights from Chicago to Cabo Real from CA $204

View CA $204 flight on Sun, Oct. 19, 2025Opens in a new window

Popular airlines from Chicago to Cabo Real

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • Viva Aerobus

    Viva Aerobus

  • Volaris

    Volaris

  • Aeromexico

    Aeromexico

  • Delta

    Delta

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Cheap flights from Chicago (CHI) to Cabo Real (SJD)

Prices were available within the past 7 days and start at CA $204 for one-way flights and CA $476 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Volaris
Sat, Oct. 11 - Sat, Oct. 18
ORD
Chicago
SJD
San José del Cabo
CA $476 Roundtrip, found 1 day ago
CA $476
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Oct. 11 from Chicago to San José del Cabo, returning Sat, Oct. 18, priced at CA $476 found 1 day ago
Volaris
Sat, Oct. 11 - Sat, Oct. 18
ORD
Chicago
SJD
San José del Cabo
CA $497 Roundtrip, found 1 day ago
CA $497
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Oct. 11 from Chicago to San José del Cabo, returning Sat, Oct. 18, priced at CA $497 found 1 day ago
Alaska Airlines
Sat, Oct. 11 - Sat, Oct. 18
ORD
Chicago
SJD
San José del Cabo
CA $508 Roundtrip, found 1 day ago
CA $508
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Oct. 11 from Chicago to San José del Cabo, returning Sat, Oct. 18, priced at CA $508 found 1 day ago
Aeromexico
Sat, Oct. 11 - Sat, Oct. 18
ORD
Chicago
SJD
San José del Cabo
CA $509 Roundtrip, found 1 day ago
CA $509
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Sat, Oct. 11 from Chicago to San José del Cabo, returning Sat, Oct. 18, priced at CA $509 found 1 day ago
American Airlines
Sun, Oct. 12 - Sat, Oct. 18
ORD
Chicago
SJD
San José del Cabo
CA $538 Roundtrip, found 1 day ago
CA $538
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Oct. 12 from Chicago to San José del Cabo, returning Sat, Oct. 18, priced at CA $538 found 1 day ago
Viva
Wed, Mar. 11 - Wed, Mar. 18
ORD
Chicago
SJD
San José del Cabo
CA $620 Roundtrip, found 4 days ago
CA $620
Roundtrip
found 4 days ago
Select Viva flight, departing Wed, Mar. 11 from Chicago to San José del Cabo, returning Wed, Mar. 18, priced at CA $620 found 4 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 $451 - CA $695 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.