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

Round-trip from

$410
(Southwest)

One-way from

$168
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$415
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. 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 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 August 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.
Thu 8/2810:40 amSJD - MDW
1 stop11h 25mSouthwest
Tue 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.
Fri 10/101:05 pmSJD - MDW
1 stop9h 30mSouthwest
Tue 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.
Wed 12/311:50 amSJD - MDW
1 stop9h 20mSouthwest
Sun 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.
Fri 11/71:47 pmSJD - MDW
1 stop7h 27mDelta
Tue 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.
Fri 11/71:05 pmSJD - MDW
1 stop8h 35mSouthwest
Tue 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.
Thu 10/3011:50 amSJD - MDW
2 stops10h 15mSouthwest
Tue 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.
Wed 9/104:50 pmSJD - MDW
2 stops24h 26mVolaris
Wed 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.
Wed 9/1012:40 pmSJD - MDW
1 stop8h 40mSouthwest
Wed 9/176:40 amMDW - SJD
1 stop8h 10mSouthwest
Deal found 8/12$501

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 August 14, 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

Thu 8/28

10:40 am-12:05 am

1 stop11h 25m

Chicago Midway

Tue 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

Thu 10/30

2:20 pm-12:10 am

1 stop7h 50m

Chicago Midway

Tue 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

Fri 10/10

1:05 pm-12:35 am

1 stop9h 30m

Chicago Midway

Tue 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

Wed 12/3

11:50 am-10:10 pm

1 stop9h 20m

Chicago Midway

Sun 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

Fri 11/7

1:47 pm-10:14 pm

1 stop7h 27m

Chicago Midway

Tue 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

Fri 11/7

1:05 pm-10:40 pm

1 stop8h 35m

Chicago Midway

Tue 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

Wed 9/10

4:50 pm-7:16 pm

2 stops24h 26m

Chicago Midway

Wed 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

Wed 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

Fri 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

Thu 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 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.

  • 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.

  • What is the cheapest month to book a flight from Los Cabos to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Los Cabos to Chicago Midway Airport (average of $160). Flying from Los Cabos 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 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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