Cheap Flights from Chicago to San José del Cabo

View €130 flight on Sun, 7 Sep 2025Opens in a new window

Popular airlines from Chicago to San José del Cabo

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

Prices were available within the past 7 days and start at €130 for one-way flights and €294 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Volaris
Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
SJD
San José del Cabo
€294 Return, found 6 days ago
€294
Return
found 6 days ago
Select Volaris flight, departing Sun, 7 Sep from Chicago to San José del Cabo, returning Mon, 15 Sep, priced at €294 found 6 days ago
Volaris
Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
SJD
San José del Cabo
€297 Return, found 6 days ago
€297
Return
found 6 days ago
Select Volaris flight, departing Sun, 7 Sep from Chicago to San José del Cabo, returning Mon, 15 Sep, priced at €297 found 6 days ago
Delta
Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
SJD
San José del Cabo
€314 Return, found 6 days ago
€314
Return
found 6 days ago
Select Delta flight, departing Sun, 7 Sep from Chicago to San José del Cabo, returning Mon, 15 Sep, priced at €314 found 6 days ago
Aeromexico
Tue, 9 Sep - Tue, 16 Sep
ORD
Chicago
SJD
San José del Cabo
€338 Return, found 3 days ago
€338
Return
found 3 days ago
Select Aeromexico flight, departing Tue, 9 Sep from Chicago to San José del Cabo, returning Tue, 16 Sep, priced at €338 found 3 days ago
American Airlines
Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
SJD
San José del Cabo
€348 Return, found 6 days ago
€348
Return
found 6 days ago
Select American Airlines flight, departing Sun, 7 Sep from Chicago to San José del Cabo, returning Mon, 15 Sep, priced at €348 found 6 days ago
United
Tue, 9 Sep - Tue, 16 Sep
ORD
Chicago
SJD
San José del Cabo
€431 Return, found 3 days ago
€431
Return
found 3 days ago
Select United flight, departing Tue, 9 Sep from Chicago to San José del Cabo, returning Tue, 16 Sep, priced at €431 found 3 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 €283 - €436 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.