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Los Cabos

$154+ Cheap flights from Midway (MDW) to Los Cabos

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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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Cheap flight deals from Midway to Los Cabos

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$385
(Delta)

One-way from

$154
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$614
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
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From Chicago Midway to Los Cabos
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One-way flight from Chicago Midway to Los Cabos
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Highest demand for flights based on searches. 6% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 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 Midway to Los Cabos

Cheapest flights from Midway to Los Cabos
Explore the most affordable flight options available from Midway to Los Cabos. 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.
Tue 12/166:40 pmMDW - SJD
2 stops18h 30mDelta
Wed 12/241:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 11/19$385
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.
Fri 11/286:00 amMDW - SJD
1 stop7h 10mDelta
Sat 12/62:40 pmSJD - MDW
1 stop8h 07mDelta
Deal found 11/19$410
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.
Sat 11/298:10 amMDW - SJD
Nonstop4h 50mSouthwest
Tue 12/21:05 pmSJD - MDW
1 stop6h 50mSouthwest
Deal found 11/19$436
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.
Fri 12/125:30 amMDW - SJD
1 stop10h 20mSouthwest
Fri 12/1911:50 amSJD - MDW
2 stops8h 30mSouthwest
Deal found 11/20$450
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.
Tue 12/166:40 pmMDW - SJD
2 stops18h 30mDelta
Mon 12/229:40 amSJD - MDW
2 stops11h 42mDelta
Deal found 11/19$465
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.
Tue 12/166:00 amMDW - SJD
1 stop7h 10mDelta
Fri 12/263:15 pmSJD - MDW
1 stop16h 50mDelta
Deal found 11/19$468
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.
Thu 12/186:00 amMDW - SJD
1 stop7h 10mDelta
Thu 12/254:35 pmSJD - MDW
2 stops15h 14mDelta
Deal found 11/20$473
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.
Tue 12/95:15 amMDW - SJD
2 stops10h 35mSouthwest
Tue 12/162:40 pmSJD - MDW
2 stops13h 25mSouthwest
Deal found 11/20$485
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.
Wed 12/247:00 amMDW - SJD
1 stop7h 10mSouthwest
Sun 12/284:30 pmSJD - MDW
1 stop7h 40mSouthwest
Deal found 11/20$498
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:00 amMDW - SJD
1 stop7h 10mAeromexico
Tue 12/161:15 pmSJD - MDW
1 stop9h 32mAeromexico
Deal found 11/20$500

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Los Cabos 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 Chicago Midway Airport to Los Cabos that are best for you.

Fly from

Midway

Fly to

Los Cabos

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 12/16

6:40 pm-12:10 pm

2 stops18h 30m

San José del Cabo Los Cabos

Tue 12/23

1:52 pm-10:22 pm

1 stop7h 30m

$385

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Fri 3/6

6:05 am-10:44 pm

2 stops15h 39m

$392

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 4/20

6:00 am-11:08 am

1 stop7h 08m

San José del Cabo Los Cabos

Tue 4/21

12:15 pm-9:45 pm

1 stop7h 30m

$392

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/19

6:00 am-11:08 am

1 stop7h 08m

San José del Cabo Los Cabos

Tue 4/21

12:15 pm-9:45 pm

1 stop7h 30m

$392

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/10

5:31 pm-8:40 am

2 stops16h 09m

San José del Cabo Los Cabos

Wed 1/14

9:35 am-10:07 pm

2 stops11h 32m

$397

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 12/12

5:30 am-2:50 pm

1 stop10h 20m

San José del Cabo Los Cabos

Fri 12/19

4:30 pm-1:10 am

1 stop7h 40m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 12/9

8:15 am-2:50 pm

1 stop7h 35m

San José del Cabo Los Cabos

Tue 12/16

2:40 pm-5:05 am

2 stops13h 25m

$415

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 1/29

5:05 am-11:40 am

1 stop7h 35m

San José del Cabo Los Cabos

Tue 2/3

2:35 pm-10:55 pm

1 stop7h 20m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Sat 1/31

1:45 pm-10:22 pm

1 stop7h 37m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

5:59 pm-8:40 am

2 stops15h 41m

San José del Cabo Los Cabos

Sun 1/25

4:32 pm-8:52 am

2 stops15h 20m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 20 results
1
2

Best time to book a flight from Midway to Los Cabos

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

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $393). Flying from Chicago Midway Airport to Los Cabos in February is currently the most expensive (average of $793). 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.

Reviews of airlines servicing Los Cabos

Get insights into the airlines that provide service to Los Cabos. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Los Cabos. Reviews last updated November 21, 2025.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Los Cabos to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Los Cabos. 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 Chicago Midway Airport to Los Cabos?

    Delta can get you from Chicago Midway Airport to Los Cabos in just under 18h 30m. Your travel time can differ by up to . Airlines will cover a distance of 1804 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Los Cabos 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 Chicago Midway Airport to Los Cabos?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $393). Flying from Chicago Midway Airport to Los Cabos in February is currently the most expensive (average of $793). 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

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Alternative routes for Midway to Los Cabos

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

Top airline flying from Midway to Los Cabos

Discover the top airline that operate flights from Midway to Los Cabos. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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