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Los Cabos

$167+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jun 16 — Jun 231
Mon 6/16
Mon 6/23
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 June 11, 2025.

Round-trip from

$400
(Delta)

One-way from

$167
(Delta)

Popular in

December

Cheapest in

July

Average price

$590
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 ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 11, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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 8/186:04 amMDW - SJD
1 stop7h 19mDelta
Fri 8/226:02 amSJD - MDW
2 stops13h 47mDelta
Deal found 6/10$400
This Southwest deal was found by Cheapflights users on 6/11. 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 6/305:15 amMDW - SJD
1 stop5h 50mSouthwest
Wed 7/91:15 pmSJD - MDW
1 stop9h 40mSouthwest
Deal found 6/11$430
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:39 pmMDW - SJD
1 stop13h 14mMultiple Airlines
Sun 11/28:00 amSJD - MDW
1 stop8h 34mMultiple Airlines
Deal found 6/10$476
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/169:59 pmMDW - SJD
1 stop18h 11mVolaris
Thu 6/198:41 amSJD - MDW
1 stop8h 35mVolaris
Deal found 6/10$534
This Aeromexico deal was found by Cheapflights users on 6/11. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/206:00 amMDW - SJD
1 stop7h 30mAeromexico
Mon 10/277:10 pmSJD - MDW
2 stops24h 34mAeromexico
Deal found 6/11$583

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 June 11, 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

Mon 8/18

6:04 am-11:23 am

1 stop7h 19m

San José del Cabo Los Cabos

Fri 8/22

6:02 am-9:49 pm

2 stops13h 47m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 6/30

5:15 am-9:05 am

1 stop5h 50m

San José del Cabo Los Cabos

Wed 7/9

1:15 pm-12:55 am

1 stop9h 40m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 7/5

8:39 pm-7:35 am

1 stop12h 56m

San José del Cabo Los Cabos

Fri 7/11

8:10 am-7:16 pm

1 stop9h 06m

$521

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 6/16

9:59 pm-2:10 pm

1 stop18h 11m

San José del Cabo Los Cabos

Thu 6/19

8:41 am-7:16 pm

1 stop8h 35m

$534

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 7/21

6:00 am-11:22 am

1 stop7h 22m

San José del Cabo Los Cabos

Wed 7/30

12:27 pm-6:02 pm

1 stop27h 35m

$611

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 7/13

12:43 pm-1:14 pm

2 stops26h 31m

San José del Cabo Los Cabos

Sat 7/19

12:25 pm-9:45 am

2 stops19h 20m

$3,721

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/18

6:04 am-4:56 pm

2 stops12h 52m

$167

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 7/28

6:10 am-1:40 pm

2 stops9h 30m

$208

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 8/16

2:44 pm-11:29 am

3 stops22h 45m

$211

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 7/12

8:39 pm-4:46 pm

1 stop22h 07m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 11 results
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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.

Rainfall in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Los Cabos ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit Los Cabos when rainfall is around 0.0 in.

Temperature in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Los Cabos, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

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 June 11, 2025.
To help decide which airline to fly from Chicago to Los Cabos, see what other customers have to say about Southwest, Delta and Aeromexico. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,706 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Volaris
6.7
Okay
1,170 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Los Cabos one-way?

    One-way options have recently been found by users for as low as $167 on Delta. Other airlines that offer cheap prices include Southwest from $208 and Volaris from $215 one-way.

  • 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

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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
O'Hare Intl to Loreto flights
Midway to La Paz 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 June 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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