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$222+ Cheap flights from Los Cabos to Midway (MDW)

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Los Cabos to Midway

Keep the following information in mind while searching for Los Cabos to Midway flight deals. Data was last updated June 18, 2025.

Round-trip from

$370
(Delta)

One-way from

$222
(Delta)

Popular in

May

Cheapest in

September

Average price

$530
From Los Cabos to Chicago Midway
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One-way flight from Los Cabos to Chicago Midway
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Highest demand for flights based on searches. 27% potential increase in price ($249 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($84 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 Los Cabos to Midway

Cheapest flights from Los Cabos to Midway
Explore the most affordable flight options available from Los Cabos to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 9/196:00 amSJD - MDW
2 stops13h 44mDelta
Mon 9/226:00 amMDW - SJD
2 stops15h 07mDelta
Deal found 6/16$370
This Southwest deal was found by Cheapflights users on 6/17. 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.
Thu 7/101:05 pmSJD - MDW
1 stop10h 00mSouthwest
Mon 7/215:50 amMDW - SJD
1 stop6h 50mSouthwest
Deal found 6/17$408
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sat 6/288:41 amSJD - MDW
1 stop8h 35mMultiple Airlines
Tue 7/18:39 pmMDW - SJD
1 stop20h 16mMultiple Airlines
Deal found 6/17$477
This eDestinos deal was found by Cheapflights users on 6/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/96:41 pmSJD - MDW
1 stop19h 59mVolaris
Wed 7/168:39 pmMDW - SJD
1 stop22h 07mVolaris
Deal found 6/18$571
This Trip.com deal was found by Cheapflights users on 6/17. 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.
Fri 8/112:27 pmSJD - MDW
1 stop25h 10mAeromexico
Fri 8/86:00 amMDW - SJD
1 stop7h 22mAeromexico
Deal found 6/17$646

Cheapflights Fare Finder

Customize your flight search to find flights from Los Cabos to Midway 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 18, 2025.
Use the filters below to find and compare flights from Los Cabos to Chicago Midway Airport that are best for you.

Fly from

Los Cabos

Fly to

Midway

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 9/19

6:00 am-9:44 pm

2 stops13h 44m

Chicago Midway

Mon 9/22

6:00 am-7:07 pm

2 stops15h 07m

$370

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/10

1:05 pm-1:05 am

1 stop10h 00m

Chicago Midway

Mon 7/21

5:50 am-10:40 am

1 stop6h 50m

$408

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 6/28

8:41 am-7:16 pm

1 stop8h 35m

Chicago Midway

Tue 7/1

8:39 pm-2:55 pm

1 stop20h 16m

$477

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 7/9

6:41 pm-4:40 pm

1 stop19h 59m

Chicago Midway

Wed 7/16

8:39 pm-4:46 pm

1 stop22h 07m

$571

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 8/1

12:27 pm-3:37 pm

1 stop25h 10m

Chicago Midway

Fri 8/8

6:00 am-11:22 am

1 stop7h 22m

$646

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 8/6

2:15 pm-8:44 am

2 stops16h 29m

$222

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 10/7

11:15 am-11:35 pm

1 stop10h 20m

$231

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sun 8/24

8:37 pm-7:16 pm

2 stops20h 39m

$242

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/28

7:25 am-7:16 pm

1 stop9h 51m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Best time to book a flight from Los Cabos to Midway

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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 18, 2025.
Read reviews from past customers who have flown Southwest, Delta and Aeromexico from Los Cabos to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
1,714 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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
4,280 reviews

Overall

8.0

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

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 Los Cabos to Midway. 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 Los Cabos to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Los Cabos to Chicago Midway Airport are Delta ($222), Southwest ($231), and Volaris ($242).

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Los Cabos to Chicago Midway Airport (average of $160). Flying from Los Cabos to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Los Cabos?

Book flights to Los Cabos if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Los Cabos to Midway

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San José del Cabo to O'Hare Intl flights
San José del Cabo to Midway flights

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