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Cheap flights from Chicago O'Hare Intl Airport to San José del Cabo from $100

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 1/18. 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.
Delta Logo
7:15 am - 2:45 pmORD-SJD
8h 30m1 stop
Delta Logo
10:25 am - 11:18 pmSJD-ORD
11h 53m1 stop
$416Delta
Find Deal
Fri, Jan 23 - Wed, Jan 28
United Airlines Logo
5:01 am - 1:43 pmORD-SJD
10h 42m1 stop
United Airlines Logo
11:50 am - 6:03 pmSJD-ORD
4h 13mnonstop
$417United Airlines
Find Deal
Fri, Oct 24 - Wed, Oct 29
Alaska Airlines Logo
9:00 am - 12:28 pmORD-SJD
28h 28m1 stop
Alaska Airlines Logo
3:53 pm - 1:59 pmSJD-ORD
21h 06m2 stops
$418Alaska Airlines
Find Deal
Sun, Mar 1 - Fri, Mar 6
Alaska Airlines Logo
7:59 pm - 12:15 pmORD-SJD
18h 16m1 stop
Alaska Airlines Logo
11:40 am - 11:59 pmSJD-ORD
11h 19m1 stop
$419Alaska Airlines
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Thu, Oct 30 - Thu, Nov 6
American Airlines Logo
5:00 am - 3:25 pmORD-SJD
12h 25m1 stop
American Airlines Logo
12:29 pm - 5:50 pmSJD-ORD
4h 21mnonstop
$420American Airlines
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Sun, Oct 26 - Sun, Nov 2
American Airlines Logo
8:45 pm - 10:34 amORD-SJD
14h 49m1 stop
American Airlines Logo
4:23 pm - 9:36 amSJD-ORD
16h 13m1 stop
$425American Airlines
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Fri, Nov 7 - Tue, Nov 11
Volaris Logo
6:23 am - 3:25 pmORD-SJD
10h 02m1 stop
Volaris Logo
4:43 pm - 4:36 amSJD-ORD
10h 53m1 stop
$426Volaris
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Wed, Dec 3 - Sun, Dec 7
Viva Logo
1:55 am - 4:25 pmORD-SJD
16h 30m1 stop
Viva Logo
8:40 am - 12:45 amSJD-ORD
14h 05m1 stop
$432Viva
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Sat, Mar 14 - Fri, Mar 20
Volaris Logo
11:59 pm - 11:30 amORD-SJD
12h 31m1 stop
Volaris Logo
4:43 pm - 4:36 amSJD-ORD
10h 53m1 stop
$438Volaris
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Thu, Feb 12 - Mon, Feb 16
Viva Logo
12:55 am - 4:30 pmORD-SJD
16h 35m1 stop
Viva Logo
10:05 pm - 11:50 pmSJD-ORD
24h 45m1 stop
$442Viva
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Tue, Jan 13 - Sun, Jan 18

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

Our best Delta deals on Chicago O'Hare Intl Airport to San José del Cabo flight tickets
Delta
Jan 23
ORD7:15 amChicago O'Hare Intl
8h 30m
1 stop
SJD2:45 pmSan José del Cabo Los Cabos
Jan 28
SJD10:25 amSan José del Cabo Los Cabos
11h 53m
1 stop
ORD11:18 pmChicago O'Hare Intl
$416
Find similar
Delta
Oct 14
ORD6:45 amChicago O'Hare Intl
6h 57m
1 stop
SJD11:42 amSan José del Cabo Los Cabos
Oct 22
SJD6:00 amSan José del Cabo Los Cabos
15h 58m
2 stops
ORD11:58 pmChicago O'Hare Intl
$422
Find similar
Delta
Oct 25
ORD6:45 amChicago O'Hare Intl
8h 14m
1 stop
SJD12:59 pmSan José del Cabo Los Cabos
Oct 28
SJD6:00 amSan José del Cabo Los Cabos
15h 58m
2 stops
ORD11:58 pmChicago O'Hare Intl
$427
Find similar

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to San José del Cabo flight tickets
American Airlines
Oct 26
ORD5:00 amChicago O'Hare Intl
12h 25m
1 stop
SJD3:25 pmSan José del Cabo Los Cabos
Nov 2
SJD12:29 pmSan José del Cabo Los Cabos
4h 21m
ORD5:50 pmChicago O'Hare Intl
$420
Find similar
American Airlines
Nov 7
ORD8:45 pmChicago O'Hare Intl
14h 49m
1 stop
SJD10:34 amSan José del Cabo Los Cabos
Nov 11
SJD4:23 pmSan José del Cabo Los Cabos
16h 13m
1 stop
ORD9:36 amChicago O'Hare Intl
$425
Find similar
American Airlines
Nov 14
ORD10:10 amChicago O'Hare Intl
4h 49m
SJD1:59 pmSan José del Cabo Los Cabos
Nov 18
SJD12:29 pmSan José del Cabo Los Cabos
4h 21m
ORD5:50 pmChicago O'Hare Intl
$433
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 October 9, 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

Fri 1/23

7:15 am-2:45 pm

1 stop8h 30m

San José del Cabo Los Cabos

Wed 1/28

10:25 am-11:18 pm

1 stop11h 53m

$416

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 10/24

5:01 am-1:43 pm

1 stop10h 42m

San José del Cabo Los Cabos

Wed 10/29

11:50 am-6:03 pm

Nonstop4h 13m

$417

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 3/1

9:00 am-12:28 pm

1 stop28h 28m

San José del Cabo Los Cabos

Fri 3/6

3:53 pm-1:59 pm

2 stops21h 06m

$418

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 10/30

7:59 pm-12:15 pm

1 stop18h 16m

San José del Cabo Los Cabos

Thu 11/6

11:40 am-11:59 pm

1 stop11h 19m

$419

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 10/26

5:00 am-3:25 pm

1 stop12h 25m

San José del Cabo Los Cabos

Sun 11/2

12:29 pm-5:50 pm

Nonstop4h 21m

$420

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 11/7

8:45 pm-10:34 am

1 stop14h 49m

San José del Cabo Los Cabos

Tue 11/11

4:23 pm-9:36 am

1 stop16h 13m

$425

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 12/3

6:23 am-3:25 pm

1 stop10h 02m

San José del Cabo Los Cabos

Sun 12/7

4:43 pm-4:36 am

1 stop10h 53m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 3/14

1:55 am-4:25 pm

1 stop16h 30m

San José del Cabo Los Cabos

Fri 3/20

8:40 am-12:45 am

1 stop14h 05m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/12

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Mon 2/16

4:43 pm-4:36 am

1 stop10h 53m

$438

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/13

12:55 am-4:30 pm

1 stop16h 35m

San José del Cabo Los Cabos

Sun 1/18

10:05 pm-11:50 pm

1 stop24h 45m

$442

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, Tuesday is the cheapest day to fly to San José del Cabo from Chicago O'Hare Intl Airport. The lowest ticket price found for a Tuesday departure recently was $585. 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 $698.

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 $646. 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 $520 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 4% 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 October 2025, prices for Chicago O'Hare Intl Airport to San José del Cabo flights are approximately 19% more expensive 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

$219

Fastest flight time

4h 37m

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 $219. 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 $473.
The fastest flight from Chicago O'Hare Intl Airport to San José del Cabo takes 4h 37m
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 49m 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 $267Free CancellationRating
7.0
786 reviews
Search Viva flights
VolarisPriceFrom $310Free CancellationRating
6.7
1,149 reviews
Search Volaris flights
DeltaPriceFrom $356Free CancellationRating
7.9
7,971 reviews
Search Delta flights
American AirlinesPriceFrom $426Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
8,966 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 $447 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $664 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, 11,043 ratings). American Airlines flies from Chicago O'Hare Intl Airport to San José del Cabo around 6 times per week, with deals starting from $426 round-trip and rising to an average price of around $625.

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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