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$208+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
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Cheap 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 October 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(Delta)

One-way from

$208
(Orbitz)

Popular in

May

Cheapest in

September

Average price

$536
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
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Highest demand for flights based on searches. 41% potential increase in price ($455 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($93 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 1, 2025.

This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 11/131:15 pmSJD - MDW
1 stop9h 25mDelta
Mon 11/176:00 amMDW - SJD
1 stop7h 10mDelta
Deal found 9/30$357
This Southwest deal was found by Cheapflights users on 9/29. 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.
Fri 12/261:05 pmSJD - MDW
1 stop11h 00mSouthwest
Wed 12/315:25 amMDW - SJD
1 stop7h 45mSouthwest
Deal found 9/29$388
This Southwest deal was found by Cheapflights users on 9/30. 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 11/1312:35 pmSJD - MDW
2 stops10h 30mSouthwest
Mon 11/175:00 amMDW - SJD
2 stops10h 50mSouthwest
Deal found 9/30$392
This Delta deal was found by Cheapflights users on 10/1. 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.
Sat 11/16:00 amSJD - MDW
2 stops14h 14mDelta
Sat 11/156:00 amMDW - SJD
1 stop7h 10mDelta
Deal found 10/1$426
This Southwest deal was found by Cheapflights users on 9/29. 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 10/211:50 amSJD - MDW
1 stop8h 05mSouthwest
Mon 10/65:30 amMDW - SJD
1 stop9h 50mSouthwest
Deal found 9/29$547
This Southwest deal was found by Cheapflights users on 9/30. 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 10/3011:50 amSJD - MDW
1 stop10h 55mSouthwest
Thu 11/69:30 pmMDW - SJD
2 stops15h 10mSouthwest
Deal found 9/30$571
This Southwest deal was found by Cheapflights users on 9/29. 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.
Mon 12/294:30 pmSJD - MDW
1 stop7h 40mSouthwest
Fri 1/25:15 amMDW - SJD
1 stop10h 00mSouthwest
Deal found 9/29$572
This Delta deal was found by Cheapflights users on 9/30. 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.
Mon 12/291:52 pmSJD - MDW
1 stop7h 30mDelta
Fri 1/26:00 amMDW - SJD
1 stop9h 10mDelta
Deal found 9/30$577

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 October 1, 2025.
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

Fri 12/26

1:05 pm-1:05 am

1 stop11h 00m

Chicago Midway

Wed 12/31

5:25 am-12:10 pm

1 stop7h 45m

$388

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 11/13

12:35 pm-12:05 am

2 stops10h 30m

Chicago Midway

Mon 11/17

5:00 am-2:50 pm

2 stops10h 50m

$392

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

12:47 pm-10:14 pm

1 stop7h 27m

Chicago Midway

Sat 11/15

6:00 am-12:10 pm

1 stop7h 10m

$426

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 2/14

12:05 pm-9:46 pm

1 stop8h 41m

Chicago Midway

Tue 2/17

9:20 am-8:45 am

2 stops24h 25m

$457

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 11/18

3:05 pm-8:54 am

2 stops16h 49m

$213

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 10/30

6:00 am-10:14 pm

2 stops14h 14m

$213

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 10/28

6:00 am-10:14 pm

2 stops14h 14m

$213

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 12/10

6:00 am-11:49 pm

2 stops16h 49m

$213

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 11/20

1:15 pm-11:40 pm

1 stop9h 25m

$213

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 12/3

6:00 am-11:49 pm

2 stops16h 49m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 14 results
1
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Compare providers for flights from San José del Cabo to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San José del Cabo to Midway in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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 27m. Your travel time can differ by up to 3h 33m. 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.

  • 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.

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

    Currently, April is the cheapest month in which you can book a flight from San José del Cabo to Chicago Midway Airport (average of $160). Flying from San José del Cabo to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

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

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Alternative routes for San José del Cabo to Midway

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San José del Cabo to O'Hare Intl flights

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