Cheap Flights From Midway Intl. (MDW) To Los Cabos Intl. (SJD)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Chicago (MDW) to San José del Cabo (SJD)

The cheapest flights to Los Cabos Intl. found within the past 7 days were CA $2,337 round trip and CA $367 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,337 Roundtrip, found 3 days ago
CA $2,337
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,337 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,358 Roundtrip, found 3 days ago
CA $2,358
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,358 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,558 Roundtrip, found 3 days ago
CA $2,558
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,558 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,572 Roundtrip, found 3 days ago
CA $2,572
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,572 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,581 Roundtrip, found 3 days ago
CA $2,581
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,581 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,607 Roundtrip, found 3 days ago
CA $2,607
Roundtrip
found 3 days ago
Select Aeromexico flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,607 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,619 Roundtrip, found 3 days ago
CA $2,619
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,619 found 3 days ago
Fri, Dec 19 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,643 Roundtrip, found 3 days ago
CA $2,643
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Dec 19 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,643 found 3 days ago
Mon, Dec 22 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,644 Roundtrip, found 3 hours ago
CA $2,644
Roundtrip
found 3 hours ago
Select Aeromexico flight, departing Mon, Dec 22 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,644 found 3 hours ago
Mon, Dec 22 - Sat, Jan 3
MDW
Chicago
SJD
San José del Cabo
CA $2,692 Roundtrip, found 3 hours ago
CA $2,692
Roundtrip
found 3 hours ago
Select Aeromexico flight, departing Mon, Dec 22 from Chicago to San José del Cabo, returning Sat, Jan 3, priced at CA $2,692 found 3 hours ago
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.