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$188+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$450
(Aeromexico)

One-way from

$188
(Mytrip)

Popular in

May

Cheapest in

September

Average price

$819
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 ($446 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 January 2026
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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 January 12, 2026.

This Aeromexico deal was found by Cheapflights users on 1/9. 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 pmSJD - MDW
1 stop7h 46mAeromexico
Mon 2/166:00 amMDW - SJD
1 stop7h 40mAeromexico
Deal found 1/9$450
This eDestinos deal was found by Cheapflights users on 1/9. 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.
Tue 2/241:45 pmSJD - MDW
1 stop7h 48mAeromexico
Tue 3/36:00 amMDW - SJD
2 stops17h 27mAeromexico
Deal found 1/9$454
This Delta deal was found by Cheapflights users on 1/9. 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.
Tue 2/249:35 amSJD - MDW
2 stops11h 58mDelta
Tue 3/36:00 amMDW - SJD
2 stops12h 37mDelta
Deal found 1/9$470
This Delta deal was found by Cheapflights users on 1/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/254:56 pmSJD - MDW
2 stops15h 10mDelta
Mon 3/26:40 pmMDW - SJD
2 stops15h 00mDelta
Deal found 1/10$471
This Delta deal was found by Cheapflights users on 1/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:45 pmSJD - MDW
1 stop7h 46mDelta
Sun 3/16:00 amMDW - SJD
1 stop7h 40mDelta
Deal found 1/10$486
This Delta deal was found by Cheapflights users on 1/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/234:32 pmSJD - MDW
2 stops15h 20mDelta
Tue 1/276:14 pmMDW - SJD
2 stops15h 26mDelta
Deal found 1/10$492
This Southwest deal was found by Cheapflights users on 1/10. 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.
Fri 2/272:35 pmSJD - MDW
1 stop7h 35mSouthwest
Sun 3/15:00 amMDW - SJD
1 stop10h 30mSouthwest
Deal found 1/10$493
This Delta deal was found by Cheapflights users on 1/11. 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.
Thu 2/264:56 pmSJD - MDW
2 stops15h 10mDelta
Thu 3/56:40 pmMDW - SJD
2 stops15h 00mDelta
Deal found 1/11$502
This Southwest deal was found by Cheapflights users on 1/10. 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 1/292:35 pmSJD - MDW
1 stop7h 20mSouthwest
Mon 2/25:05 amMDW - SJD
1 stop7h 35mSouthwest
Deal found 1/10$514

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 January 12, 2026.
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

Fri 2/13

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 2/16

6:00 am-2:09 pm

1 stop9h 09m

$451

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 2/24

9:35 am-10:33 pm

2 stops11h 58m

Chicago Midway

Tue 3/3

6:00 am-5:37 pm

2 stops12h 37m

$470

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 2/25

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 3/2

6:00 am-2:09 pm

1 stop9h 09m

$471

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 2/25

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 3/2

6:00 am-10:27 pm

2 stops17h 27m

$471

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

Chicago Midway

Sun 3/1

6:40 pm-8:40 am

2 stops15h 00m

$471

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 1/23

4:32 pm-8:52 am

2 stops15h 20m

Chicago Midway

Tue 1/27

6:14 pm-8:40 am

2 stops15h 26m

$492

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/27

2:35 pm-11:10 pm

1 stop7h 35m

Chicago Midway

Sun 3/1

5:00 am-2:30 pm

1 stop10h 30m

$493

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 1/31

3:59 pm-11:13 pm

3 stops30h 14m

$266

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/12

1:35 pm-10:35 pm

1 stop8h 00m

$269

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/26

2:35 pm-11:10 pm

1 stop7h 35m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 17 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

What is the cheapest time of day to fly from KPG to MDW?

Find hourly flight availability from Los Cabos to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 12, 2026.

When flying from Los Cabos to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 46m. Fly via Aeromexico or Delta to get the fastest option. The distance from Los Cabos to Chicago Midway Airport is about 1804 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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
Merrillville
Hammond
Porter
Benton Harbor

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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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