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$168+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$410
(Southwest)

One-way from

$168
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$415
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 ($460 potential increase over avg. RT price).
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Cheapest flight prices on average. 17% potential price decrease ($94 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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.
jue. 8/2810:40 amSJD - MDW
1 stop11h 25mSouthwest
mar. 9/26:25 amMDW - SJD
1 stop7h 20mSouthwest
Deal found 8/12$410
This Southwest deal was found by Cheapflights users on 8/12. 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. 10/101:05 pmSJD - MDW
1 stop9h 30mSouthwest
mar. 10/146:25 amMDW - SJD
1 stop9h 15mSouthwest
Deal found 8/12$415
This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 12/311:50 amSJD - MDW
1 stop9h 20mSouthwest
dom. 12/145:30 amMDW - SJD
1 stop10h 20mSouthwest
Deal found 8/14$440
This Delta deal was found by Cheapflights users on 8/12. 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.
vie. 11/71:47 pmSJD - MDW
1 stop7h 27mDelta
mar. 11/116:00 amMDW - SJD
2 stops12h 22mDelta
Deal found 8/12$462
This Southwest deal was found by Cheapflights users on 8/12. 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. 11/71:05 pmSJD - MDW
1 stop8h 35mSouthwest
mar. 11/115:25 amMDW - SJD
1 stop7h 45mSouthwest
Deal found 8/12$465
This Southwest deal was found by Cheapflights users on 8/13. 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.
jue. 10/3011:50 amSJD - MDW
2 stops10h 15mSouthwest
mar. 11/45:30 amMDW - SJD
2 stops10h 20mSouthwest
Deal found 8/13$469
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/104:50 pmSJD - MDW
2 stops24h 26mVolaris
mié. 9/178:39 pmMDW - SJD
2 stops20h 59mVolaris
Deal found 8/12$495
This Southwest deal was found by Cheapflights users on 8/12. 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. 9/1012:40 pmSJD - MDW
1 stop8h 40mSouthwest
mié. 9/176:40 amMDW - SJD
1 stop8h 10mSouthwest
Deal found 8/12$501

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 agosto 14, 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

jue. 8/28

10:40 am-12:05 am

1 stop11h 25m

Chicago Midway

mar. 9/2

6:25 am-11:45 am

1 stop7h 20m

$410

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 10/30

2:20 pm-12:10 am

1 stop7h 50m

Chicago Midway

mar. 11/4

5:30 am-1:45 pm

1 stop9h 15m

$415

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 10/10

1:05 pm-12:35 am

1 stop9h 30m

Chicago Midway

mar. 10/14

6:25 am-1:40 pm

1 stop9h 15m

$415

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 12/3

11:50 am-10:10 pm

1 stop9h 20m

Chicago Midway

dom. 12/14

5:30 am-2:50 pm

1 stop10h 20m

$440

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 11/7

1:47 pm-10:14 pm

1 stop7h 27m

Chicago Midway

mar. 11/11

6:00 am-5:22 pm

2 stops12h 22m

$462

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 11/7

1:05 pm-10:40 pm

1 stop8h 35m

Chicago Midway

mar. 11/11

5:25 am-12:10 pm

1 stop7h 45m

$465

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 9/10

4:50 pm-7:16 pm

2 stops24h 26m

Chicago Midway

mié. 9/17

8:39 pm-3:38 pm

2 stops20h 59m

$495

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 9/17

12:54 pm-7:16 pm

2 stops28h 22m

$168

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 9/26

8:29 am-7:16 pm

1 stop8h 47m

$201

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 9/25

11:53 am-7:16 pm

1 stop29h 23m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 14 results
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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.

  • 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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