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Cheap flights from Chicago O'Hare Intl Airport to San José del Cabo from $104

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to San José del Cabo departing on 2/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to San José del Cabo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Viva Logo
1:20 am - 8:00 amORD-SJD
7h 40m1 stop
Viva Logo
8:30 am - 11:50 pmSJD-ORD
14h 20m1 stop
$373Viva
Find Deal
Sun, Feb 15 - Fri, Feb 20
Volaris Logo
6:23 am - 3:20 pmORD-SJD
9h 57m1 stop
Volaris Logo
12:11 pm - 10:29 pmSJD-ORD
9h 18m1 stop
$374Volaris
Find Deal
Mon, Mar 2 - Sat, Mar 7
Frontier Logo
6:03 am - 1:36 pmORD-SJD
8h 33m1 stop
Frontier Logo
3:01 pm - 2:02 pmSJD-ORD
22h 01m1 stop
$375Frontier
Find Deal
Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
12:59 pm - 10:45 amORD-SJD
22h 46m1 stop
Multiple Airlines Logo
6:30 pm - 11:50 pmSJD-ORD
28h 20m2 stops
$376Multiple Airlines
Find Deal
Fri, Feb 6 - Thu, Feb 12
Viva Logo
12:55 am - 10:45 amORD-SJD
10h 50m1 stop
Viva Logo
11:20 am - 11:25 pmSJD-ORD
11h 05m1 stop
$377Viva
Find Deal
Fri, Feb 13 - Sat, Feb 21
Viva Logo
12:55 am - 10:45 amORD-SJD
10h 50m1 stop
Viva Logo
6:30 pm - 11:50 pmSJD-ORD
52h 20m2 stops
$378Viva
Find Deal
Fri, Jan 23 - Fri, Jan 30
Frontier Logo
6:03 am - 1:36 pmORD-SJD
8h 33m1 stop
Frontier Logo
12:52 pm - 11:35 pmSJD-ORD
9h 43m1 stop
$379Frontier
Find Deal
Sat, Feb 7 - Sat, Feb 14
Multiple Airlines Logo
11:59 pm - 11:30 amORD-SJD
12h 31m1 stop
Multiple Airlines Logo
5:05 pm - 11:25 pmSJD-ORD
29h 20m1 stop
$380Multiple Airlines
Find Deal
Sat, Jan 24 - Tue, Jan 27
Multiple Airlines Logo
12:59 pm - 4:30 pmORD-SJD
28h 31m1 stop
Multiple Airlines Logo
9:00 am - 11:50 pmSJD-ORD
13h 50m2 stops
$381Multiple Airlines
Find Deal
Wed, Feb 4 - Mon, Feb 9
Multiple Airlines Logo
11:59 pm - 11:30 amORD-SJD
12h 31m1 stop
Multiple Airlines Logo
5:45 pm - 1:35 pmSJD-ORD
18h 50m1 stop
$382Multiple Airlines
Find Deal
Thu, Jan 22 - Sun, Jan 25

Viva flights from Chicago O'Hare Intl Airport to San José del Cabo

Our best Viva deals on Chicago O'Hare Intl Airport to San José del Cabo flight tickets
Viva
Feb 15
ORD1:20 amChicago O'Hare Intl
7h 40m
1 stop
SJD8:00 amSan José del Cabo Los Cabos
Feb 20
SJD8:30 amSan José del Cabo Los Cabos
14h 20m
1 stop
ORD11:50 pmChicago O'Hare Intl
$373
Find similar
Viva
Feb 13
ORD12:55 amChicago O'Hare Intl
10h 50m
1 stop
SJD10:45 amSan José del Cabo Los Cabos
Feb 21
SJD11:20 amSan José del Cabo Los Cabos
11h 05m
1 stop
ORD11:25 pmChicago O'Hare Intl
$377
Find similar
Viva
Jan 23
ORD12:55 amChicago O'Hare Intl
10h 50m
1 stop
SJD10:45 amSan José del Cabo Los Cabos
Jan 30
SJD6:30 pmSan José del Cabo Los Cabos
52h 20m
2 stops
ORD11:50 pmChicago O'Hare Intl
$378
Find similar

United Airlines flights from Chicago O'Hare Intl Airport to San José del Cabo

Our best United Airlines deals on Chicago O'Hare Intl Airport to San José del Cabo flight tickets
United Airlines
Dec 14
ORD9:03 amChicago O'Hare Intl
5h 00m
SJD1:03 pmSan José del Cabo Los Cabos
Dec 17
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
$404
Find similar
United Airlines
Dec 9
ORD6:00 amChicago O'Hare Intl
9h 32m
1 stop
SJD2:32 pmSan José del Cabo Los Cabos
Dec 16
SJD12:50 pmSan José del Cabo Los Cabos
4h 11m
ORD6:01 pmChicago O'Hare Intl
$408
Find similar
United Airlines
Dec 14
ORD6:00 amChicago O'Hare Intl
9h 32m
1 stop
SJD2:32 pmSan José del Cabo Los Cabos
Dec 17
SJD12:49 pmSan José del Cabo Los Cabos
7h 27m
1 stop
ORD9:16 pmChicago O'Hare Intl
$418
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to San José del Cabo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 26, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San José del Cabo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 2/15

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Fri 2/20

8:30 am-11:50 pm

1 stop14h 20m

$373

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 3/2

6:23 am-3:20 pm

1 stop9h 57m

San José del Cabo Los Cabos

Sat 3/7

12:11 pm-10:29 pm

1 stop9h 18m

$374

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

6:03 am-1:36 pm

1 stop8h 33m

San José del Cabo Los Cabos

Sat 1/31

3:01 pm-2:02 pm

1 stop22h 01m

$375

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/6

12:59 pm-10:45 am

1 stop22h 46m

San José del Cabo Los Cabos

Thu 2/12

6:30 pm-11:50 pm

2 stops28h 20m

$376

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/13

12:55 am-10:45 am

1 stop10h 50m

San José del Cabo Los Cabos

Sat 2/21

11:20 am-11:25 pm

1 stop11h 05m

$377

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/23

12:55 am-10:45 am

1 stop10h 50m

San José del Cabo Los Cabos

Fri 1/30

6:30 pm-11:50 pm

2 stops52h 20m

$378

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/7

6:03 am-1:36 pm

1 stop8h 33m

San José del Cabo Los Cabos

Sat 2/14

12:52 pm-11:35 pm

1 stop9h 43m

$379

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Tue 1/27

5:05 pm-11:25 pm

1 stop29h 20m

$380

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 2/4

12:59 pm-4:30 pm

1 stop28h 31m

San José del Cabo Los Cabos

Mon 2/9

9:00 am-11:50 pm

2 stops13h 50m

$381

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 1/22

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Sun 1/25

5:45 pm-1:35 pm

1 stop18h 50m

$382

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José del Cabo from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to San José del Cabo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José del Cabo?

The cheapest month to fly to San José del Cabo from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $491, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in September, then August is your next best option. Flight prices from Chicago O'Hare Intl Airport to San José del Cabo during August average around $526.

What is the cheapest day to depart on your flight to San José del Cabo?

According to our data, Monday is the cheapest day to fly to San José del Cabo from Chicago O'Hare Intl Airport. The lowest ticket price found for a Monday departure recently was $588. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $701.

What is the cheapest time of day to depart on your flight to San José del Cabo?

Flying to San José del Cabo from Chicago O'Hare Intl Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $313 when looking at flights departing in the afternoon. Flights to San José del Cabo are more costly in the morning, with an average ticket price of $638. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago O'Hare Intl to San José del Cabo Los Cabos flight route?

Fly from Chicago O'Hare Intl to San José del Cabo Los Cabos for the best Chicago O'Hare Intl - San José del Cabo Los Cabos flight prices

How far in advance should I book a flight to San José del Cabo?

You are more likely to see cheaper flights to San José del Cabo from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $607 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José del Cabo from Chicago O'Hare Intl Airport for as low as $542 on momondo.

What cabin class options are available on Chicago O'Hare Intl to San José del Cabo Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl to San José del Cabo Los Cabos flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to San José del Cabo flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago O'Hare Intl Airport to San José del Cabo flight.

How have Chicago O'Hare Intl Airport to San José del Cabo flight prices changed over time?

As of November 2025, prices for Chicago O'Hare Intl Airport to San José del Cabo flights are approximately 19% cheaper when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to San José del Cabo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to San José del Cabo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to San José del Cabo (ORD to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to San José del Cabo

Best Price Found

$242

Fastest flight time

4h 40m

Direct flights

Every day

Airports in San José del Cabo

1 airport
The best one-way flight to San José del Cabo from Chicago O'Hare Intl Airport in the past 72 hours is $242. The best round-trip flight deal from Chicago O'Hare Intl Airport to San José del Cabo found on momondo in the last 72 hours is $522.
The fastest flight from Chicago O'Hare Intl Airport to San José del Cabo takes 4h 40m
Direct flights go from Chicago O'Hare Intl Airport to San José del Cabo every day.
There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)
Search flight deals

  • How far is Chicago O'Hare Intl to San José del Cabo Los Cabos by plane?

    The distance between Chicago O'Hare Intl and San José del Cabo Los Cabos is about 1810.6 mi. 4h 53m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport?

    Prices for flights from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to San José del Cabo Los Cabos Airport.

  • What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?

    The travel and health documents required for your trip to San José del Cabo Los Cabos Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José del Cabo Los Cabos Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to San José del Cabo?

  • What is the most popular airline from Chicago O'Hare Intl Airport to San José del Cabo?

Best airlines flying from Chicago O'Hare Intl Airport to San José del Cabo

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to San José del Cabo with momondo
Airline
Rating
Free Cancellation
Price
VivaPriceFrom $266Free CancellationRating
7.0
789 reviews
Search Viva flights
VolarisPriceFrom $308Free CancellationRating
6.7
1,154 reviews
Search Volaris flights
DeltaPriceFrom $356Free CancellationRating
7.9
8,003 reviews
Search Delta flights
American AirlinesPriceFrom $418Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom $442Free CancellationRating
7.4
9,050 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago O'Hare Intl Airport to San José del Cabo

    United Airlines flight deals from Chicago O'Hare Intl Airport to San José del Cabo start from $442 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $662 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago O'Hare Intl Airport to San José del Cabo

    Another popular option for Chicago O'Hare Intl Airport to San José del Cabo flights is American Airlines (7.2/10, 11,038 ratings). American Airlines flies from Chicago O'Hare Intl Airport to San José del Cabo around 13 times per week, with deals starting from $418 round-trip and rising to an average price of around $612.

Traveling to a place near San José del Cabo?

Book flights to San José del Cabo if you plan to visit one of these locations
Todos Santos
Los Barriles

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José del Cabo?

It is quick and easy to find Chicago to San José del Cabo flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to San José del Cabo that suits you.

Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?

Yes. All flights to San José del Cabo from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to San José del Cabo?

Once all potential Chicago to San José del Cabo flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to San José del Cabo flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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