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$223+ Cheap flights from San José del Cabo (SJD) to Midway (MDW)

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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from San José del Cabo to Midway

Cheapest flights from San José del Cabo to Midway
Explore the most affordable flight options available from San José del Cabo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This Southwest deal was found by Cheapflights users on 2/10. 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.
Thu 3/122:30 pm
SJD
-
MDW
1 stop12h 05m
Southwest
Mon 3/166:05 am
MDW
-
SJD
1 stop8h 15m
Southwest
Deal found 2/10$473
This Aeromexico deal was found by Cheapflights users on 2/8. 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.
Fri 2/131:45 pm
SJD
-
MDW
1 stop7h 46m
Aeromexico
Mon 2/166:00 am
MDW
-
SJD
1 stop7h 40m
Aeromexico
Deal found 2/8$477
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 3/1112:35 pm
SJD
-
MDW
1 stop7h 56m
Delta
Sun 3/1510:45 am
MDW
-
SJD
2 stops13h 44m
Delta
Deal found 2/11$607

Find flight deals from San José del Cabo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José del Cabo (SJD) to Midway (MDW). 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$473
(Southwest)

One-way from

$223
(Southwest)

Popular in

May

Cheapest in

September

Average price

$620

Good one-way deal

$245 or less
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago Midway flights.
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From San José del Cabo Los Cabos to Chicago Midway
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One-way flight from San José del Cabo Los Cabos to Chicago Midway
Search Deals
Highest demand for flights based on searches. 50% potential increase in price ($773 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 32% potential price decrease ($187 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Price to beat on a one-way flight from San José del Cabo Los Cabos to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Midway 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 February 12, 2026.
Use the filters below to find and compare flights from San José del Cabo to Chicago Midway Airport that are best for you.

Fly from

San José del Cabo

Fly to

Midway

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 3/12

2:30 pm-4:35 am

1 stop12h 05m

Chicago Midway

Mon 3/16

6:05 am-12:20 pm

1 stop8h 15m

$473

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 3/11

12:35 pm-10:31 pm

1 stop7h 56m

Chicago Midway

Sun 3/15

10:45 am-10:29 pm

2 stops13h 44m

$607

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 3/11

1:50 pm-12:10 am

1 stop8h 20m

Chicago Midway

Sun 3/15

9:30 am-12:25 pm

Nonstop4h 55m

$761

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sun 2/22

1:35 pm-10:35 pm

1 stop8h 00m

Chicago Midway

Sat 2/28

6:50 am-3:35 pm

2 stops9h 45m

$863

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 3/12

6:05 am-10:31 pm

2 stops14h 26m

Chicago Midway

Mon 3/16

6:00 am-5:43 pm

2 stops13h 43m

$1,233

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$228

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/27

1:35 pm-10:35 pm

1 stop8h 00m

$228

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 3/24

10:10 am-4:05 pm

Nonstop3h 55m

$228

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/27

4:56 pm-8:54 am

2 stops14h 58m

$232

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 5/15

1:35 pm-8:42 am

2 stops17h 07m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 17 results
1
2
  • Most accurate provider: When it comes to deals on San José del Cabo-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José del Cabo-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José del Cabo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José del Cabo-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San José del Cabo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San José del Cabo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José del Cabo 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.

Related info for your journey

Find useful and relevant information for your journey from San José del Cabo to Midway. 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 from for flights from San José del Cabo to Chicago Midway?

    For a flight from San José del Cabo to Chicago Midway, you will be flying from Los Cabos. San José del Cabo Los Cabos (SJD) is just 6.6 mi from the center of the city. Los Cabos is the only San José del Cabo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from San José del Cabo Los Cabos on a regular basis.

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

    Southwest and Delta can get you from San José del Cabo to Chicago Midway Airport in just under 7h 56m. Your travel time can differ by up to 4h 09m. There are 1804 mi between San José del Cabo and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from San José del Cabo to Chicago Midway Airport?

    Looking for the cheapest flight from San José del Cabo to Chicago Midway Airport? While on average our users pay $274, our data indicates the cheapest price to be $245. The most popular route (San José del Cabo Los Cabos - Chicago Midway), is priced around $556.

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

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

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

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

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

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

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for San José del Cabo to Midway

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