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San José del Cabo

$163+ Cheap flights from Midway (MDW) to San José del Cabo (SJD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Midway to San José del Cabo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José del Cabo (SJD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 16, 2025.

Round-trip from

$432
(Delta)

One-way from

$163
(Southwest)

Popular in

December

Cheapest in

October

Average price

$502
From Chicago Midway to San José del Cabo Los Cabos
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One-way flight from Chicago Midway to San José del Cabo Los Cabos
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Highest demand for flights based on searches. 21% potential increase in price ($198 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to San José del Cabo

Cheapest flights from Midway to San José del Cabo
Explore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/295:25 amMDW - SJD
2 stops9h 20mSouthwest
mié. 1/72:20 pmSJD - MDW
2 stops13h 45mSouthwest
Deal found 9/16$437
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/145:10 amMDW - SJD
1 stop9h 35mSouthwest
mar. 11/182:40 pmSJD - MDW
1 stop7h 15mSouthwest
Deal found 9/15$450
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/295:45 amMDW - SJD
2 stops9h 05mSouthwest
mié. 10/11:45 pmSJD - MDW
1 stop7h 15mSouthwest
Deal found 9/16$453
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/187:05 amMDW - SJD
2 stops8h 45mSouthwest
lun. 11/2411:50 amSJD - MDW
2 stops8h 25mSouthwest
Deal found 9/16$455
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/225:25 amMDW - SJD
1 stop10h 30mSouthwest
jue. 11/2712:15 pmSJD - MDW
1 stop6h 50mSouthwest
Deal found 9/14$461
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/186:00 amMDW - SJD
2 stops10h 30mDelta
sáb. 10/2512:47 pmSJD - MDW
1 stop7h 27mDelta
Deal found 9/14$463
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/65:25 amMDW - SJD
2 stops9h 55mSouthwest
vie. 10/102:20 pmSJD - MDW
1 stop7h 50mSouthwest
Deal found 9/15$468
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/115:35 amMDW - SJD
2 stops8h 35mSouthwest
mar. 11/182:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 9/16$469
This Aeromexico deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/296:00 amMDW - SJD
2 stops28h 27mAeromexico
mié. 12/39:42 amSJD - MDW
2 stops12h 50mAeromexico
Deal found 9/16$479
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/298:10 amMDW - SJD
Nonstop4h 50mSouthwest
mié. 12/31:05 pmSJD - MDW
1 stop8h 50mSouthwest
Deal found 9/16$486
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/195:25 amMDW - SJD
1 stop10h 25mSouthwest
dom. 11/232:05 pmSJD - MDW
1 stop8h 15mSouthwest
Deal found 9/15$490

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 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

Midway

Fly to

San José del Cabo

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 12/29

5:25 am-1:45 pm

2 stops9h 20m

San José del Cabo Los Cabos

mié. 1/7

2:20 pm-5:05 am

2 stops13h 45m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 11/15

4:28 pm-2:00 pm

2 stops22h 32m

San José del Cabo Los Cabos

lun. 11/24

1:17 pm-11:32 pm

1 stop9h 15m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 1/18

6:00 am-6:20 pm

2 stops13h 20m

San José del Cabo Los Cabos

sáb. 1/24

1:40 pm-9:46 pm

1 stop7h 06m

$477

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 12/13

6:20 am-12:00 pm

1 stop6h 40m

San José del Cabo Los Cabos

dom. 12/21

11:50 am-9:15 pm

1 stop8h 25m

$506

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 11/18

6:00 am-5:22 pm

2 stops12h 22m

San José del Cabo Los Cabos

mar. 11/25

9:32 am-11:32 pm

2 stops13h 00m

$560

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 11/28

6:00 am-6:10 pm

2 stops13h 10m

San José del Cabo Los Cabos

sáb. 12/6

2:40 pm-11:32 pm

1 stop7h 52m

$576

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 12/30

6:05 am-12:30 pm

1 stop7h 25m

San José del Cabo Los Cabos

mar. 1/6

2:35 pm-10:55 pm

1 stop7h 20m

$581

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 2/21

6:00 am-6:10 pm

2 stops13h 10m

San José del Cabo Los Cabos

sáb. 2/28

12:05 pm-9:46 pm

1 stop8h 41m

$596

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 3/8

5:05 am-2:25 pm

1 stop11h 20m

San José del Cabo Los Cabos

dom. 3/15

1:50 pm-11:55 pm

1 stop8h 05m

$605

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 11/19

6:00 am-6:07 pm

2 stops13h 07m

San José del Cabo Los Cabos

lun. 11/24

1:17 pm-11:32 pm

1 stop9h 15m

$605

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 results
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Best time to book a flight from Midway to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing San José del Cabo

Get insights into the airlines that provide service to San José del Cabo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José del Cabo. Reviews last updated septiembre 16, 2025.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to San José del Cabo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San José del Cabo from Chicago Midway?

    Located just 6.6 mi from the city center, San José del Cabo Los Cabos is the airport most travelers will use when flying to San José del Cabo from Chicago Midway. Booking flights from Chicago Midway to Los Cabos (SJD) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • How long is the flight from Chicago Midway Airport to San José del Cabo?

    For as low as $437, Southwest can have you in San José del Cabo from Chicago Midway Airport in 9h 20m. The distance between Chicago Midway Airport and San José del Cabo is about 1804 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to San José del Cabo round-trip?

    According to our current data, Southwest ($545), offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Southwest is 26% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Midway to San José del Cabo that include hotel bookings?

    Yes. In addition to deals on Midway to San José del Cabo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to San José del Cabo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San José del Cabo.

  • Can I find deals for business class flights from Midway to San José del Cabo?

    Yes. Cheapflights offers flight deals from Midway to San José del Cabo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San José del Cabo?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $437). Flying from Chicago Midway Airport to San José del Cabo in March is currently the most expensive (average of $549). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to San José del Cabo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to San José del Cabo flights
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Top airline flying from Midway to San José del Cabo

Discover the top airline that operate flights from Midway to San José del Cabo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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