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Los Cabos

$155+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
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 August 13, 2025.

Round-trip from

$431
(Southwest)

One-way from

$155
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$551
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. 8% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 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 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 August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/10. 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 9/96:40 amMDW - SJD
1 stop8h 10mSouthwest
Tue 9/1612:40 pmSJD - MDW
1 stop8h 40mSouthwest
Deal found 8/10$431
This SmartFares deal was found by Cheapflights users on 8/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amMDW - SJD
1 stop7h 10mAeromexico
Fri 11/211:17 pmSJD - MDW
1 stop7h 27mAeromexico
Deal found 8/11$434
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.
Sun 10/197:45 amMDW - SJD
1 stop6h 55mSouthwest
Thu 10/2311:50 amSJD - MDW
2 stops10h 15mSouthwest
Deal found 8/12$436
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.
Mon 10/206:00 amMDW - SJD
1 stop7h 42mDelta
Sat 10/2512:47 pmSJD - MDW
1 stop7h 27mDelta
Deal found 8/12$452
This Southwest deal was found by Cheapflights users on 8/11. 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.
Wed 11/268:00 amMDW - SJD
1 stop7h 15mSouthwest
Wed 12/311:50 amSJD - MDW
1 stop9h 20mSouthwest
Deal found 8/11$455
This Southwest deal was found by Cheapflights users on 8/11. 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.
Sat 9/137:40 amMDW - SJD
1 stop7h 30mSouthwest
Thu 9/181:45 pmSJD - MDW
1 stop7h 55mSouthwest
Deal found 8/11$457
This Delta deal was found by Cheapflights users on 8/11. 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.
Tue 11/259:20 amMDW - SJD
2 stops29h 10mDelta
Thu 12/43:02 pmSJD - MDW
2 stops26h 34mDelta
Deal found 8/11$460
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 8/185:45 amMDW - SJD
2 stops9h 05mSouthwest
Fri 8/2212:40 pmSJD - MDW
1 stop9h 25mSouthwest
Deal found 8/11$462
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.
Thu 9/48:39 pmMDW - SJD
2 stops17h 35mVolaris
Thu 9/184:50 pmSJD - MDW
2 stops24h 26mVolaris
Deal found 8/12$470
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 9/295:45 amMDW - SJD
1 stop6h 00mSouthwest
Sun 10/512:45 pmSJD - MDW
1 stop9h 50mSouthwest
Deal found 8/11$476
This Southwest deal was found by Cheapflights users on 8/11. 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.
Wed 9/106:40 amMDW - SJD
1 stop8h 10mSouthwest
Wed 9/1712:40 pmSJD - MDW
1 stop8h 40mSouthwest
Deal found 8/11$477
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 10/68:45 pmMDW - SJD
2 stops15h 35mSouthwest
Sat 10/111:25 pmSJD - MDW
1 stop7h 10mSouthwest
Deal found 8/11$481

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 August 13, 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

Sun 9/21

6:00 am-1:10 pm

1 stop9h 10m

San José del Cabo Los Cabos

Wed 9/24

12:40 pm-11:20 pm

1 stop8h 40m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 9/9

6:40 am-12:50 pm

1 stop8h 10m

San José del Cabo Los Cabos

Tue 9/16

12:40 pm-11:20 pm

1 stop8h 40m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/14

7:30 am-1:40 pm

1 stop8h 10m

San José del Cabo Los Cabos

Tue 10/21

12:45 pm-12:05 am

1 stop9h 20m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/28

6:00 am-1:10 pm

1 stop9h 10m

San José del Cabo Los Cabos

Fri 10/3

1:30 pm-12:05 am

2 stops8h 35m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 10/19

6:45 am-1:05 pm

1 stop8h 20m

San José del Cabo Los Cabos

Fri 10/24

11:50 am-12:05 am

2 stops10h 15m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 10/19

7:45 am-12:40 pm

1 stop6h 55m

San José del Cabo Los Cabos

Thu 10/23

11:50 am-12:05 am

2 stops10h 15m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 10/20

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Sat 10/25

12:47 pm-10:14 pm

1 stop7h 27m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/15

5:45 am-12:50 pm

2 stops9h 05m

San José del Cabo Los Cabos

Sat 9/20

2:05 pm-10:45 pm

1 stop6h 40m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 10/19

6:30 am-11:45 am

1 stop7h 15m

San José del Cabo Los Cabos

Sat 10/25

1:25 pm-10:35 pm

1 stop7h 10m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 9/25

8:39 pm-4:34 pm

2 stops21h 55m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 17 results
1
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $437). Flying from Chicago Midway Airport to Los Cabos in March is currently the most expensive (average of $549). 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 August 13, 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
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $437). Flying from Chicago Midway Airport to Los Cabos in March is currently the most expensive (average of $549). 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

Browse thousands of different options on Cheapflights for your next trip

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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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