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Cheap flights from Chicago to San José del Cabo from $94

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 to San José del Cabo departing on 4/18. 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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0 bags

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Find the cheapest flights from Chicago to San José del Cabo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Viva Logo
12:55 am - 4:25 pm
ORD
-
SJD
16h 30m
1 stop
Viva Logo
8:40 am - 11:45 pm
SJD
-
ORD
14h 05m
1 stop
$451Viva
Sat, Feb 28 - Fri, Mar 6
Viva Logo
12:55 am - 4:30 pm
ORD
-
SJD
16h 35m
1 stop
Viva Logo
8:30 am - 11:50 pm
SJD
-
ORD
14h 20m
1 stop
$452Viva
Thu, Feb 19 - Fri, Feb 27
Viva Logo
12:20 pm - 12:25 pm
ORD
-
SJD
26h 05m
1 stop
Viva Logo
8:40 am - 12:45 am
SJD
-
ORD
14h 05m
1 stop
$458Viva
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
8:40 pm - 11:40 am
MDW
-
SJD
16h 00m
2 stops
Southwest Logo
2:20 pm - 12:35 am
SJD
-
MDW
9h 15m
1 stop
$462Southwest
Mon, Feb 23 - Fri, Feb 27
Volaris Logo
11:59 pm - 3:19 pm
ORD
-
SJD
16h 20m
3 stops
Volaris Logo
12:59 pm - 4:36 am
SJD
-
ORD
14h 37m
2 stops
$463Volaris
Sat, Jan 31 - Tue, Feb 3
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m
2 stops
Delta Logo
1:45 pm - 10:33 pm
SJD
-
MDW
7h 48m
1 stop
$483Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m
2 stops
Delta Logo
4:56 pm - 9:06 am
SJD
-
MDW
15h 10m
2 stops
$487Delta
Tue, Feb 17 - Tue, Feb 24
Aeromexico Logo
12:45 pm - 9:31 am
MDW
-
SJD
21h 46m
2 stops
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m
2 stops
$488Aeromexico
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
5:05 am - 11:40 am
MDW
-
SJD
7h 35m
1 stop
Southwest Logo
2:35 pm - 10:55 pm
SJD
-
MDW
7h 20m
1 stop
$503Southwest
Tue, Feb 3 - Tue, Feb 10
Aeromexico Logo
12:45 pm - 9:31 am
MDW
-
SJD
21h 46m
2 stops
Aeromexico Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
$504Aeromexico
Mon, Feb 16 - Fri, Feb 20

Southwest flights from Chicago to San José del Cabo

Our best Southwest deals on Chicago to San José del Cabo flight tickets
Southwest
Feb 23
MDW8:40 pmChicago Midway
16h 00m
2 stops
SJD11:40 amSan José del Cabo Los Cabos
Feb 27
SJD2:20 pmSan José del Cabo Los Cabos
9h 15m
1 stop
MDW12:35 amChicago Midway
$462
Southwest
Feb 3
MDW5:05 amChicago Midway
7h 35m
1 stop
SJD11:40 amSan José del Cabo Los Cabos
Feb 10
SJD2:35 pmSan José del Cabo Los Cabos
7h 20m
1 stop
MDW10:55 pmChicago Midway
$503
Southwest
May 6
MDW8:55 pmChicago Midway
18h 30m
2 stops
SJD1:25 pmSan José del Cabo Los Cabos
May 13
SJD12:25 pmSan José del Cabo Los Cabos
8h 55m
1 stop
MDW11:20 pmChicago Midway
$521

Volaris flights from Chicago to San José del Cabo

Our best Volaris deals on Chicago to San José del Cabo flight tickets
Volaris
Jan 31
ORD11:59 pmChicago O'Hare Intl
16h 20m
3 stops
SJD3:19 pmSan José del Cabo Los Cabos
Feb 3
SJD12:59 pmSan José del Cabo Los Cabos
14h 37m
2 stops
ORD4:36 amChicago O'Hare Intl
$463
Volaris
Feb 2
ORD11:58 pmChicago O'Hare Intl
19h 09m
3 stops
SJD6:07 pmSan José del Cabo Los Cabos
Feb 9
SJD12:59 pmSan José del Cabo Los Cabos
14h 37m
2 stops
ORD4:36 amChicago O'Hare Intl
$469
Volaris
Feb 18
ORD6:23 amChicago O'Hare Intl
9h 57m
1 stop
SJD3:20 pmSan José del Cabo Los Cabos
Feb 22
SJD4:08 pmSan José del Cabo Los Cabos
11h 28m
1 stop
ORD4:36 amChicago O'Hare Intl
$475

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago 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

Sat 2/28

12:55 am-4:25 pm

1 stop16h 30m

San José del Cabo Los Cabos

Fri 3/6

8:40 am-11:45 pm

1 stop14h 05m

$451

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/19

12:55 am-4:30 pm

1 stop16h 35m

San José del Cabo Los Cabos

Fri 2/27

8:30 am-11:50 pm

1 stop14h 20m

$452

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 4/9

12:20 pm-12:25 pm

1 stop26h 05m

San José del Cabo Los Cabos

Thu 4/16

8:40 am-12:45 am

1 stop14h 05m

$458

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/23

8:40 pm-11:40 am

2 stops16h 00m

San José del Cabo Los Cabos

Fri 2/27

2:20 pm-12:35 am

1 stop9h 15m

$462

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/31

11:59 pm-3:19 pm

3 stops16h 20m

San José del Cabo Los Cabos

Tue 2/3

12:59 pm-4:36 am

2 stops14h 37m

$463

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 3/3

1:45 pm-10:33 pm

1 stop7h 48m

$483

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/17

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 2/24

4:56 pm-9:06 am

2 stops15h 10m

$487

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/23

12:45 pm-9:31 am

2 stops21h 46m

San José del Cabo Los Cabos

Thu 2/26

6:05 am-10:31 pm

2 stops15h 26m

$488

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/3

5:05 am-11:40 am

1 stop7h 35m

San José del Cabo Los Cabos

Tue 2/10

2:35 pm-10:55 pm

1 stop7h 20m

$503

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/16

12:45 pm-9:31 am

2 stops21h 46m

San José del Cabo Los Cabos

Fri 2/20

1:45 pm-10:31 pm

1 stop7h 46m

$504

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 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 typical price of a round-trip flight between Chicago and San José del Cabo?

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

The cheapest month to fly to San José del Cabo from Chicago is in September. Flight prices, which tend to average around $482, 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 to San José del Cabo during August average around $543.

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. The lowest ticket price found for a Tuesday departure recently was $590. 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $685.

What is the cheapest Chicago 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 - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $600 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 for as low as $533 on momondo.

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

There are 3 cabin classes available to choose from on Chicago 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 to San José del Cabo flights?

You could potentially save up to 17% on your flight if you consider stops on a Chicago to San José del Cabo flight.

How have Chicago to San José del Cabo flight prices changed over time?

As of January 2026, prices for Chicago to San José del Cabo flights are approximately 29% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to San José del Cabo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to San José del Cabo (CHI to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San José del Cabo

Best Price Found

$282

Fastest flight time

4h 36m

Direct flights

Every day

Airports in San José del Cabo

1 airport
The best one-way flight to San José del Cabo from Chicago in the past 72 hours is $282. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $571.
The fastest flight from Chicago to San José del Cabo takes 4h 36m
Direct flights go from Chicago to San José del Cabo every day.
There is 1 airport in San José del Cabo. From Chicago there are direct flights to San José del Cabo Los Cabos (SJD).
Search flight deals

  • How far is Chicago to San José del Cabo Los Cabos by plane?

    There are 1817.1 mi between Chicago and San José del Cabo Los Cabos. By plane, this route typically takes 4h 36m.

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago 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 to San José del Cabo?

  • What is the most popular airline from Chicago to San José del Cabo?

Best airlines flying from Chicago to San José del Cabo

Compare and see reviews for airlines that fly from Chicago to San José del Cabo with momondo
Airline
Rating
Free Cancellation
Price
VolarisPriceFrom $253Free CancellationRating
6.6
1,172 reviews
Search Volaris flights
VivaPriceFrom $266Free CancellationRating
7.0
818 reviews
Search Viva flights
DeltaPriceFrom $278Free CancellationRating
7.9
8,085 reviews
Search Delta flights
American AirlinesPriceFrom $417Free CancellationRating
7.2
11,172 reviews
Search American Airlines flights
United AirlinesPriceFrom $420Free CancellationRating
7.4
9,190 reviews
Search United Airlines flights
SouthwestPriceFrom $485Free CancellationRating
8.0
4,266 reviews
Search Southwest flights

  • United Airlines Flights From Chicago to San José del Cabo

    United Airlines flight deals from Chicago to San José del Cabo start from $420 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $647 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to San José del Cabo

    American Airlines (7.2/10 from 11,172 reviews) operates around 12 flights from Chicago to San José del Cabo in any given week. The average American Airlines airfare for this route is around $607, with deals from around $417 rare but found on momondo. Referenced prices are for round-trip Chicago to San José del Cabo flight searches in the last 72 hours.

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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San José del Cabo. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Chicago to San José del Cabo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to San José del Cabo from Chicago.

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 offers price alerts on flights to San José del Cabo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your San José del Cabo trip

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