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Cheap flights from Chicago Midway Airport to San José del Cabo from $161

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 Midway Airport to San José del Cabo departing on 11/29. 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 Midway Airport to San José del Cabo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 am - 11:40 amMDW-SJD
7h 10m1 stop
Southwest Logo
1:05 pm - 8:55 pmSJD-MDW
6h 50m1 stop
$418Southwest
Find Deal
Fri, Nov 28 - Wed, Dec 3
Southwest Logo
8:25 am - 2:20 pmMDW-SJD
6h 55m1 stop
Southwest Logo
2:40 pm - 10:55 pmSJD-MDW
7h 15m1 stop
$419Southwest
Find Deal
Sat, Nov 15 - Wed, Nov 19
Southwest Logo
8:15 am - 2:50 pmMDW-SJD
7h 35m1 stop
Southwest Logo
3:45 pm - 1:30 amSJD-MDW
8h 45m1 stop
$420Southwest
Find Deal
Mon, Nov 3 - Fri, Nov 7
Southwest Logo
5:00 am - 1:10 pmMDW-SJD
9h 10m2 stops
Southwest Logo
4:30 pm - 1:10 amSJD-MDW
7h 40m1 stop
$423Southwest
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Tue, Nov 18 - Tue, Nov 25
Delta Logo
6:00 am - 11:42 amMDW-SJD
7h 42m1 stop
Delta Logo
1:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
$505Delta
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Fri, Oct 31 - Fri, Nov 7
Volaris Logo
6:49 pm - 10:36 amMDW-SJD
17h 47m2 stops
Volaris Logo
3:02 pm - 5:34 pmSJD-MDW
24h 32m2 stops
$531Volaris
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Sun, Mar 8 - Sat, Mar 14
Delta Logo
6:00 am - 6:10 pmMDW-SJD
13h 10m2 stops
Delta Logo
9:32 am - 11:40 pmSJD-MDW
13h 08m2 stops
$533Delta
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Fri, Nov 7 - Tue, Nov 11
Volaris Logo
6:49 pm - 10:36 amMDW-SJD
17h 47m2 stops
Volaris Logo
5:37 pm - 5:34 pmSJD-MDW
21h 57m2 stops
$540Volaris
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Sun, Mar 22 - Sat, Mar 28
Aeromexico Logo
10:35 am - 8:45 amMDW-SJD
23h 10m2 stops
Aeromexico Logo
6:05 am - 9:46 pmSJD-MDW
14h 41m2 stops
$592Aeromexico
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Sat, Jan 10 - Sat, Jan 31
Aeromexico Logo
5:00 am - 11:42 amMDW-SJD
7h 42m1 stop
Aeromexico Logo
6:00 am - 11:47 pmSJD-MDW
16h 47m2 stops
$613Aeromexico
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Sun, Nov 2 - Tue, Dec 2

Volaris flights from Chicago Midway Airport to San José del Cabo

Our best Volaris deals on Chicago Midway Airport to San José del Cabo flight tickets
Volaris
Mar 8
MDW6:49 pmChicago Midway
17h 47m
2 stops
SJD10:36 amSan José del Cabo Los Cabos
Mar 14
SJD3:02 pmSan José del Cabo Los Cabos
24h 32m
2 stops
MDW5:34 pmChicago Midway
$531
Find similar
Volaris
Mar 22
MDW6:49 pmChicago Midway
17h 47m
2 stops
SJD10:36 amSan José del Cabo Los Cabos
Mar 28
SJD5:37 pmSan José del Cabo Los Cabos
21h 57m
2 stops
MDW5:34 pmChicago Midway
$540
Find similar
Volaris
Feb 11
MDW6:54 pmChicago Midway
21h 46m
2 stops
SJD3:40 pmSan José del Cabo Los Cabos
Feb 15
SJD12:59 pmSan José del Cabo Los Cabos
27h 35m
3 stops
MDW5:34 pmChicago Midway
$582
Find similar

Southwest flights from Chicago Midway Airport to San José del Cabo

Our best Southwest deals on Chicago Midway Airport to San José del Cabo flight tickets
Southwest
Nov 28
MDW5:30 amChicago Midway
7h 10m
1 stop
SJD11:40 amSan José del Cabo Los Cabos
Dec 3
SJD1:05 pmSan José del Cabo Los Cabos
6h 50m
1 stop
MDW8:55 pmChicago Midway
$418
Find similar
Southwest
Nov 15
MDW8:25 amChicago Midway
6h 55m
1 stop
SJD2:20 pmSan José del Cabo Los Cabos
Nov 19
SJD2:40 pmSan José del Cabo Los Cabos
7h 15m
1 stop
MDW10:55 pmChicago Midway
$419
Find similar
Southwest
Nov 3
MDW8:15 amChicago Midway
7h 35m
1 stop
SJD2:50 pmSan José del Cabo Los Cabos
Nov 7
SJD3:45 pmSan José del Cabo Los Cabos
8h 45m
1 stop
MDW1:30 amChicago Midway
$420
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway 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 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José del Cabo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

5:30 am-11:40 am

1 stop7h 10m

San José del Cabo Los Cabos

Wed 12/3

1:05 pm-8:55 pm

1 stop6h 50m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/15

8:25 am-2:20 pm

1 stop6h 55m

San José del Cabo Los Cabos

Wed 11/19

2:40 pm-10:55 pm

1 stop7h 15m

$419

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 11/3

8:15 am-2:50 pm

1 stop7h 35m

San José del Cabo Los Cabos

Fri 11/7

3:45 pm-1:30 am

1 stop8h 45m

$420

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 11/18

5:00 am-1:10 pm

2 stops9h 10m

San José del Cabo Los Cabos

Tue 11/25

4:30 pm-1:10 am

1 stop7h 40m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 10/31

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Fri 11/7

1:47 pm-10:14 pm

1 stop7h 27m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/8

6:49 pm-10:36 am

2 stops17h 47m

San José del Cabo Los Cabos

Sat 3/14

3:02 pm-5:34 pm

2 stops24h 32m

$531

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/7

6:00 am-6:10 pm

2 stops13h 10m

San José del Cabo Los Cabos

Tue 11/11

9:32 am-11:40 pm

2 stops13h 08m

$533

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/22

6:49 pm-10:36 am

2 stops17h 47m

San José del Cabo Los Cabos

Sat 3/28

5:37 pm-5:34 pm

2 stops21h 57m

$540

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/10

10:35 am-8:45 am

2 stops23h 10m

San José del Cabo Los Cabos

Sat 1/31

6:05 am-9:46 pm

2 stops14h 41m

$592

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 11/2

5:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Tue 12/2

6:00 am-11:47 pm

2 stops16h 47m

$613

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 Midway 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 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 Midway Airport. The lowest ticket price found for a Tuesday 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 Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $703.

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 Midway 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 $644. 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 Midway to San José del Cabo Los Cabos flight route?

Fly from Chicago Midway to San José del Cabo Los Cabos for the best Chicago Midway - San José del Cabo Los Cabos flight prices

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

There is only 1 cabin class available to choose from on Chicago Midway 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 Midway Airport to San José del Cabo flights?

You could potentially save up to 3% on your flight if you consider stops on a Chicago Midway Airport to San José del Cabo flight.

When to book flights from Chicago Midway Airport to San José del Cabo

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

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

Fastest flight time

4h 50m

Direct flights

Mon and Sun

Airports in San José del Cabo

1 airport
The fastest flight from Chicago Midway Airport to San José del Cabo takes 4h 50m
Direct flights go from Chicago Midway Airport to San José del Cabo on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)
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  • How far is Chicago Midway to San José del Cabo Los Cabos by plane?

    Chicago Midway and San José del Cabo Los Cabos are 1808.5 mi apart from one another. Typically, this will take 4h 50m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport are updated daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway 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 you'll need for your trip to San José del Cabo Los Cabos Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José del Cabo Los Cabos Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San José del Cabo?

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

Best airlines flying from Chicago Midway Airport to San José del Cabo

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José del Cabo with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $545Free CancellationRating
8.0
4,235 reviews
Search Southwest flights

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?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San José del Cabo from Chicago.

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

All flight searches from Chicago to San José del Cabo on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San José del Cabo.

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

If you are simply researching potential flights to San José del Cabo, momondo offers a useful price alert feature which will track prices for flights to San José del Cabo from Chicago and alert you when they change.

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