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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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$426
(Aeromexico)

One-way from

$167
(Delta)

Popular in

December

Cheapest in

September

Average price

$502
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 ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This Aeromexico deal was found by Cheapflights users on 9/28. 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.
Thu 11/276:00 amMDW - SJD
1 stop7h 10mAeromexico
Fri 12/121:15 pmSJD - MDW
1 stop9h 34mAeromexico
Deal found 9/28$426
This Delta deal was found by Cheapflights users on 9/28. 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 10/296:00 amMDW - SJD
1 stop7h 42mDelta
Sat 11/12:04 pmSJD - MDW
2 stops17h 36mDelta
Deal found 9/28$431
This Southwest deal was found by Cheapflights users on 9/27. 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 12/157:05 amMDW - SJD
1 stop7h 40mSouthwest
Fri 12/1911:50 amSJD - MDW
2 stops8h 30mSouthwest
Deal found 9/27$454
This Southwest deal was found by Cheapflights users on 9/27. 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 11/185:00 amMDW - SJD
2 stops10h 50mSouthwest
Mon 11/241:05 pmSJD - MDW
1 stop8h 45mSouthwest
Deal found 9/27$459
This Delta deal was found by Cheapflights users on 9/27. 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.
Sat 10/47:15 pmMDW - SJD
2 stops19h 58mDelta
Tue 10/72:25 pmSJD - MDW
2 stops25h 18mDelta
Deal found 9/27$466
This Delta deal was found by Cheapflights users on 9/27. 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 12/69:32 amSJD - MDW
2 stops13h 17mDelta
Deal found 9/27$471
This Delta deal was found by Cheapflights users on 9/28. 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 11/126:00 amMDW - SJD
2 stops13h 07mDelta
Wed 11/191:15 pmSJD - MDW
1 stop9h 25mDelta
Deal found 9/28$484
This Southwest deal was found by Cheapflights users on 9/27. 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 12/167:00 amMDW - SJD
1 stop7h 10mSouthwest
Mon 12/222:05 pmSJD - MDW
1 stop9h 50mSouthwest
Deal found 9/27$493
This Southwest deal was found by Cheapflights users on 9/28. 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 12/37:00 amMDW - SJD
1 stop7h 10mSouthwest
Sat 12/62:05 pmSJD - MDW
1 stop7h 10mSouthwest
Deal found 9/28$498
This Aeromexico deal was found by Cheapflights users on 9/27. 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 9/306:00 amMDW - SJD
1 stop7h 25mAeromexico
Tue 10/78:13 pmSJD - MDW
2 stops24h 01mAeromexico
Deal found 9/27$501

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 September 29, 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

Fri 1/9

6:00 am-2:00 pm

1 stop9h 00m

San José del Cabo Los Cabos

Fri 1/16

1:40 pm-9:46 pm

1 stop7h 06m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

5:00 am-11:40 am

1 stop7h 40m

San José del Cabo Los Cabos

Fri 3/6

11:35 am-10:00 pm

1 stop9h 25m

$432

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/6

9:32 am-11:49 pm

2 stops13h 17m

$471

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/10

6:00 am-2:00 pm

1 stop9h 00m

San José del Cabo Los Cabos

Sat 1/31

1:40 pm-9:46 pm

1 stop7h 06m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/2

6:45 pm-10:45 am

1 stop17h 00m

San José del Cabo Los Cabos

Sat 3/7

1:40 pm-9:46 pm

1 stop7h 06m

$477

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 11/2

5:30 am-2:50 pm

1 stop10h 20m

San José del Cabo Los Cabos

Mon 11/17

2:40 pm-10:55 pm

1 stop7h 15m

$493

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/14

6:25 am-1:40 pm

1 stop9h 15m

San José del Cabo Los Cabos

Sat 10/18

12:50 pm-10:50 pm

1 stop8h 00m

$524

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 2/1

5:55 am-11:40 am

1 stop6h 45m

San José del Cabo Los Cabos

Sun 2/15

2:05 pm-12:25 am

1 stop9h 20m

$533

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/1

5:00 am-10:40 am

1 stop7h 40m

San José del Cabo Los Cabos

Tue 11/4

2:40 pm-10:55 pm

1 stop7h 15m

$544

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/7

9:40 pm-2:20 pm

2 stops17h 40m

San José del Cabo Los Cabos

Fri 11/14

12:35 pm-12:05 am

2 stops10h 30m

$549

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 18 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
No data available for this route at this time. Please check back soon.

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 September 29, 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

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

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 and Southwest can get you from Chicago Midway Airport to Los Cabos in just under 7h 40m. Your travel time can differ by up to 1h 20m. Airlines will cover a distance of 1804 mi. This flight may include one or multiple stops.

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

    On average you can expect to pay $954 for a flight from Chicago Midway Airport to Los Cabos. The cheapest flight overall is $695 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $381.

  • 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
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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$717FlexibilityNo cancel feeOn-time63%

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