Cheap Flights From O'Hare Intl. (ORD) 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 (ORD) to San José del Cabo (SJD)

The cheapest flights to Los Cabos Intl. found within the past 7 days were CA $531 round trip and CA $225 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Jun 22 - Mon, Jun 29
ORD
Chicago
SJD
San José del Cabo
CA $531 Roundtrip, found 4 days ago
CA $531
Roundtrip
found 4 days ago
Select Volaris flight, departing Mon, Jun 22 from Chicago to San José del Cabo, returning Mon, Jun 29, priced at CA $531 found 4 days ago
Thu, May 7 - Sun, May 10
ORD
Chicago
SJD
San José del Cabo
CA $543 Roundtrip, found 2 days ago
CA $543
Roundtrip
found 2 days ago
Select Volaris flight, departing Thu, May 7 from Chicago to San José del Cabo, returning Sun, May 10, priced at CA $543 found 2 days ago
Wed, May 20 - Sun, May 24
ORD
Chicago
SJD
San José del Cabo
CA $575 Roundtrip, found 2 days ago
CA $575
Roundtrip
found 2 days ago
Select Volaris flight, departing Wed, May 20 from Chicago to San José del Cabo, returning Sun, May 24, priced at CA $575 found 2 days ago
Thu, Apr 23 - Sun, Apr 26
ORD
Chicago
SJD
San José del Cabo
CA $589 Roundtrip, found 2 days ago
CA $589
Roundtrip
found 2 days ago
Select Volaris flight, departing Thu, Apr 23 from Chicago to San José del Cabo, returning Sun, Apr 26, priced at CA $589 found 2 days ago
Mon, Jun 15 - Sat, Jun 20
ORD
Chicago
SJD
San José del Cabo
CA $589 Roundtrip, found 19 hours ago
CA $589
Roundtrip
found 19 hours ago
Select Volaris flight, departing Mon, Jun 15 from Chicago to San José del Cabo, returning Sat, Jun 20, priced at CA $589 found 19 hours ago
Thu, Feb 19 - Thu, Feb 26
ORD
Chicago
SJD
San José del Cabo
CA $603 Roundtrip, found 5 days ago
CA $603
Roundtrip
found 5 days ago
Select Volaris flight, departing Thu, Feb 19 from Chicago to San José del Cabo, returning Thu, Feb 26, priced at CA $603 found 5 days ago
Wed, May 20 - Sun, May 24
ORD
Chicago
SJD
San José del Cabo
CA $604 Roundtrip, found 2 days ago
CA $604
Roundtrip
found 2 days ago
Select Volaris flight, departing Wed, May 20 from Chicago to San José del Cabo, returning Sun, May 24, priced at CA $604 found 2 days ago
Mon, Jun 15 - Sat, Jun 20
ORD
Chicago
SJD
San José del Cabo
CA $611 Roundtrip, found 19 hours ago
CA $611
Roundtrip
found 19 hours ago
Select Volaris flight, departing Mon, Jun 15 from Chicago to San José del Cabo, returning Sat, Jun 20, priced at CA $611 found 19 hours ago
Mon, Jun 15 - Sat, Jun 20
ORD
Chicago
SJD
San José del Cabo
CA $621 Roundtrip, found 19 hours ago
CA $621
Roundtrip
found 19 hours ago
Select Volaris flight, departing Mon, Jun 15 from Chicago to San José del Cabo, returning Sat, Jun 20, priced at CA $621 found 19 hours ago
Thu, May 14 - Sun, May 17
ORD
Chicago
SJD
San José del Cabo
CA $621 Roundtrip, found 2 days ago
CA $621
Roundtrip
found 2 days ago
Select Volaris flight, departing Thu, May 14 from Chicago to San José del Cabo, returning Sun, May 17, priced at CA $621 found 2 days ago

Frequently asked questions

Are there direct flights from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
If you're eager to journey from O'Hare Airport to SJD as quickly as possible, you'll be pleased to know multiple airlines offer direct flights. Pick your preferred seat with United Airlines or American Airlines.
What airlines fly from ORD to Los Cabos Airport?
If you're going to Los Cabos from Chicago, you'll find a few airlines offering direct flights. One of the most reputable carriers is United Airlines (UA), which offers 17 flights each month. An alternative is American Airlines (AA), which has 13 flights every month. The more airlines you look into, the more likely you are to sniff out a terrific deal.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.
*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.