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$205+ Cheap flights from Los Cabos 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Dez 21 — Dez 281
So 12/21
So 12/28
1 adult, Economy
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Cheap flight deals from Los Cabos to Midway

Keep the following information in mind while searching for Los Cabos to Midway flight deals. Data was last updated November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$330
(Delta)

One-way from

$205
(Priceline)

Popular in

May

Cheapest in

September

Average price

$494
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago (CHI) flights.
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From Los Cabos to Chicago Midway
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One-way flight from Los Cabos to Chicago Midway
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Highest demand for flights based on searches. 40% potential increase in price ($439 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($92 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Los Cabos to Midway

Cheapest flights from Los Cabos to Midway
Explore the most affordable flight options available from Los Cabos to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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.
Mo 12/291:52 pmSJD - MDW
1 stop7h 30mDelta
Fr 1/26:00 amMDW - SJD
1 stop7h 47mDelta
Deal found 11/19$330
This Delta deal was found by Cheapflights users on 11/20. 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.
Di 12/234:35 pmSJD - MDW
2 stops15h 30mDelta
Do 1/16:00 amMDW - SJD
1 stop9h 10mDelta
Deal found 11/20$364
This Southwest deal was found by Cheapflights users on 11/19. 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.
Di 12/302:40 pmSJD - MDW
1 stop9h 30mSouthwest
So 1/46:05 amMDW - SJD
1 stop7h 25mSouthwest
Deal found 11/19$394
This Southwest deal was found by Cheapflights users on 11/20. 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.
Di 12/2311:50 amSJD - MDW
2 stops8h 30mSouthwest
Do 1/15:00 amMDW - SJD
2 stops9h 10mSouthwest
Deal found 11/20$471
This Southwest deal was found by Cheapflights users on 11/20. 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.
Mi 11/261:25 pmSJD - MDW
1 stop9h 15mSouthwest
Mo 12/18:05 amMDW - SJD
1 stop6h 40mSouthwest
Deal found 11/20$501
This Southwest deal was found by Cheapflights users on 11/20. 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.
Mi 11/2611:50 amSJD - MDW
2 stops8h 30mSouthwest
Mi 12/37:05 amMDW - SJD
1 stop7h 40mSouthwest
Deal found 11/20$614
This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/221:20 pmSJD - MDW
1 stop19h 20mMultiple Airlines
Fr 12/268:00 amMDW - SJD
2 stops25h 32mMultiple Airlines
Deal found 11/20$832

Cheapflights Fare Finder

 
Customize your flight search to find flights from Los Cabos 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 November 21, 2025.
Use the filters below to find and compare flights from Los Cabos to Chicago Midway Airport that are best for you.

Fly from

Los Cabos

Fly to

Midway

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mo 12/29

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Fr 1/2

6:00 am-12:47 pm

1 stop7h 47m

$330

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Di 12/23

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Do 1/1

6:00 am-2:10 pm

1 stop9h 10m

$332

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fr 2/13

1:40 pm-10:44 pm

1 stop8h 04m

Chicago Midway

Di 2/17

6:00 am-2:00 pm

1 stop9h 00m

$337

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Di 12/30

2:40 pm-1:10 am

1 stop9h 30m

Chicago Midway

So 1/4

6:05 am-12:30 pm

1 stop7h 25m

$394

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sa 2/14

12:05 pm-10:44 pm

1 stop9h 39m

Chicago Midway

Di 2/17

10:53 am-8:45 am

2 stops22h 52m

$452

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sa 12/20

1:25 pm-6:30 pm

Nonstop4h 05m

$207

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sa 1/24

6:05 am-10:22 pm

2 stops15h 17m

$210

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sa 1/17

1:45 pm-10:07 pm

1 stop7h 22m

$210

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

So 1/25

4:32 pm-8:52 am

2 stops15h 20m

$210

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mo 1/26

1:45 pm-10:22 pm

1 stop7h 37m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 15 results
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Best time to book a flight from Los Cabos to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Los Cabos 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.

Cheapflights Insights

Everything you need to know about your flight from Los Cabos to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

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

  • How long is the flight from Los Cabos to Chicago Midway Airport?

    There are many flights that can get you from Los Cabos to Chicago Midway Airport in 7h 30m. Fly via Delta to get the fastest option. The distance from Los Cabos to Chicago Midway Airport is about 1804 mi.

  • Can I find deals for flights from Los Cabos to Midway that include hotel bookings?

    Yes. In addition to deals on Los Cabos to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Los Cabos to Midway?

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

  • Can I find deals for business class flights from Los Cabos to Midway?

    Yes. Cheapflights offers flight deals from Los Cabos 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
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Los Cabos to Midway

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

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