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$210+ Cheap flights from San José del Cabo (SJD) 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from San José del Cabo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José del Cabo (SJD) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$336
(Delta)

One-way from

$210
(Delta)

Popular in

May

Cheapest in

September

Average price

$530
From San José del Cabo Los Cabos to Chicago Midway
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One-way flight from San José del Cabo 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 San José del Cabo to Midway

Cheapest flights from San José del Cabo to Midway
Explore the most affordable flight options available from San José del Cabo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:01 amSJD - MDW
2 stops13h 43mDelta
Tue 10/146:00 amMDW - SJD
1 stop7h 30mDelta
Deal found 6/11$336
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 7/101:05 pmSJD - MDW
1 stop7h 45mSouthwest
Wed 7/165:55 amMDW - SJD
1 stop7h 05mSouthwest
Deal found 6/12$408
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1012:27 pmSJD - MDW
1 stop25h 10mAeromexico
Wed 7/306:00 amMDW - SJD
1 stop7h 22mAeromexico
Deal found 6/10$566

Cheapflights Fare Finder

Customize your flight search to find flights from San José del Cabo 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 12, 2025.
Use the filters below to find and compare flights from San José del Cabo to Chicago Midway Airport that are best for you.

Fly from

San José del Cabo

Fly to

Midway

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 10/9

6:01 am-9:44 pm

2 stops13h 43m

Chicago Midway

Tue 10/14

6:00 am-11:30 am

1 stop7h 30m

$336

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/10

1:05 pm-10:50 pm

1 stop7h 45m

Chicago Midway

Wed 7/16

5:55 am-11:00 am

1 stop7h 05m

$408

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/10

12:27 pm-3:37 pm

1 stop25h 10m

Chicago Midway

Wed 7/30

6:00 am-11:22 am

1 stop7h 22m

$566

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 8/19

2:07 pm-8:35 am

2 stops16h 28m

$210

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 7/15

1:15 pm-12:55 am

1 stop9h 40m

$226

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 8/8

7:51 pm-8:54 pm

2 stops23h 03m

$253

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 7/15

4:15 pm-7:16 pm

2 stops25h 01m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from San José del Cabo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José del Cabo 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 San José del Cabo 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 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
1,706 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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 San José del Cabo to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José del Cabo to Chicago Midway?

    For a flight from San José del Cabo to Chicago Midway, you will be flying from Los Cabos. San José del Cabo Los Cabos (SJD) is just 6.6 mi from the center of the city. Los Cabos is the only San José del Cabo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from San José del Cabo Los Cabos on a regular basis.

  • What are the cheapest airlines to fly from San José del Cabo to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $210. However, be on the lookout for offers from Southwest and Volaris, as they are both options that can get you from San José del Cabo to Chicago Midway Airport for a low price.

  • Can I find deals for flights from San José del Cabo to Midway that include hotel bookings?

    Yes. In addition to deals on San José del Cabo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José del Cabo to Midway?

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

  • Can I find deals for business class flights from San José del Cabo to Midway?

    Yes. Cheapflights offers flight deals from San José del Cabo 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 San José del Cabo to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from San José del Cabo to Chicago Midway Airport (average of $160). Flying from San José del Cabo 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 San José del Cabo?

Book flights to San José del Cabo if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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