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$217+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$387
(Delta)

One-way from

$217
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$368
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago (CHI) flights.
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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. 18% potential increase in price ($133 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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 5/246:06 amSJD - MDW
2 stops13h 07mDelta
Sat 5/316:00 amMDW - SJD
1 stop8h 43mDelta
Deal found 4/30$387
This Aeromexico deal was found by Cheapflights users on 5/1. 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.
Wed 7/912:27 pmSJD - MDW
1 stop27h 35mAeromexico
Wed 7/166:00 amMDW - SJD
1 stop7h 22mAeromexico
Deal found 5/1$598
This Southwest deal was found by Cheapflights users on 4/30. 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 7/271:50 pmSJD - MDW
1 stop9h 15mSouthwest
Sat 8/28:40 amMDW - SJD
1 stop6h 50mSouthwest
Deal found 4/30$601

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 May 1, 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

Sat 5/24

6:06 am-9:13 pm

2 stops13h 07m

Chicago Midway

Sat 5/31

6:00 am-12:43 pm

1 stop8h 43m

$387

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 7/9

12:27 pm-6:02 pm

1 stop27h 35m

Chicago Midway

Wed 7/16

6:00 am-11:22 am

1 stop7h 22m

$598

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sun 7/27

1:50 pm-1:05 am

1 stop9h 15m

Chicago Midway

Sat 8/2

8:40 am-1:30 pm

1 stop6h 50m

$601

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 5/30

12:54 pm-8:53 pm

3 stops29h 59m

$217

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 6/5

3:32 pm-7:16 pm

1 stop25h 44m

$235

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 5/29

6:06 am-9:27 pm

2 stops13h 21m

$238

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 7/1

11:55 am-11:50 pm

1 stop9h 55m

$242

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 6/6

2:30 pm-5:47 pm

3 stops25h 17m

$460

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 10/11

1:40 pm-5:58 pm

1 stop26h 18m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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 May 1, 2025.
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Volaris ($235), Delta ($238), and Southwest ($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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Los Cabos to Midway

See prices for flight routes from nearby airports that may be better suited for you.
San José del Cabo to O'Hare Intl flights
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