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Los Cabos

$140+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$483
(Southwest)

One-way from

$140
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$574
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. 7% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 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 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 January 11, 2026.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:05 amMDW - SJD
1 stop7h 35mSouthwest
Tue 3/312:35 pmSJD - MDW
1 stop9h 15mSouthwest
Deal found 1/11$483
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.
Mon 2/98:40 pmMDW - SJD
2 stops16h 00mSouthwest
Fri 2/1312:00 pmSJD - MDW
2 stops10h 10mSouthwest
Deal found 1/10$487
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.
Tue 1/275:05 amMDW - SJD
1 stop7h 35mSouthwest
Wed 2/412:35 pmSJD - MDW
1 stop9h 15mSouthwest
Deal found 1/10$493
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:55 pmMDW - SJD
2 stops17h 45mSouthwest
Wed 2/1112:35 pmSJD - MDW
2 stops9h 05mSouthwest
Deal found 1/9$497
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.
Sun 3/110:15 pmMDW - SJD
1 stop13h 50mSouthwest
Fri 3/61:35 pmSJD - MDW
Nonstop3h 55mSouthwest
Deal found 1/10$502
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.
Mon 1/266:00 amMDW - SJD
1 stop7h 40mDelta
Fri 1/301:45 pmSJD - MDW
1 stop7h 37mDelta
Deal found 1/10$503
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.
Mon 4/136:30 amMDW - SJD
1 stop8h 16mDelta
Fri 4/2412:15 pmSJD - MDW
1 stop8h 14mDelta
Deal found 1/11$510
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 amMDW - SJD
1 stop9h 09mAeromexico
Tue 3/31:45 pmSJD - MDW
1 stop7h 48mAeromexico
Deal found 1/10$519
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/108:55 pmMDW - SJD
2 stops15h 45mSouthwest
Tue 2/172:05 pmSJD - MDW
1 stop9h 20mSouthwest
Deal found 1/11$520

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 January 11, 2026.
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

Sun 5/3

6:00 am-11:20 am

1 stop7h 20m

San José del Cabo Los Cabos

Fri 5/8

2:20 pm-5:45 am

1 stop13h 25m

$483

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/10

5:05 am-11:40 am

1 stop7h 35m

San José del Cabo Los Cabos

Tue 2/17

2:05 pm-12:25 am

1 stop9h 20m

$493

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

Fri 1/30

1:45 pm-10:22 pm

1 stop7h 37m

$503

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/17

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 2/24

1:45 pm-10:33 pm

1 stop7h 48m

$503

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

5:15 am-1:55 pm

2 stops9h 40m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$506

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/10

6:14 pm-8:40 am

2 stops15h 26m

San José del Cabo Los Cabos

Tue 2/17

9:35 am-10:33 pm

2 stops11h 58m

$507

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 4/13

6:30 am-12:46 pm

1 stop8h 16m

San José del Cabo Los Cabos

Fri 4/24

12:15 pm-10:29 pm

1 stop8h 14m

$510

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 3/3

6:05 am-10:33 pm

2 stops15h 28m

$522

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:15 am-1:10 pm

1 stop7h 55m

$219

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 5/10

6:00 am-5:41 pm

2 stops13h 41m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 18 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $471). Flying from Chicago Midway Airport to Los Cabos in February is currently the most expensive (average of $1,112). 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.

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

Find hourly flight availability from Midway to Los Cabos. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 11, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Los Cabos as you normally would.

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 January 11, 2026.
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
4,253 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    Southwest can get you from Chicago Midway Airport to Los Cabos in just under 7h 55m. Your travel time can differ by up to . Airlines will cover a distance of 1804 mi.

  • What are the cheapest flights from Chicago Midway Airport to Los Cabos?

    On average you can expect to pay $626 for a flight from Chicago Midway Airport to Los Cabos. The cheapest flight overall is $604 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $431.

  • 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $471). Flying from Chicago Midway Airport to Los Cabos in February is currently the most expensive (average of $1,112). 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$485Average$697FlexibilityNo cancel feeOn-time63%

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