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San José del Cabo

$167+ Cheap flights from Midway (MDW) to San José del Cabo (SJD)

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 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Midway to San José del Cabo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José del Cabo (SJD). 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

$400
(Delta)

One-way from

$167
(Delta)

Popular in

November

Cheapest in

August

Average price

$620
From Chicago Midway to San José del Cabo Los Cabos
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One-way flight from Chicago Midway to San José del Cabo Los Cabos
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Highest demand for flights based on searches. 7% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($34 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 San José del Cabo

Cheapest flights from Midway to San José del Cabo
Explore the most affordable flight options available from Midway to San José del Cabo. 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 6/10. 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 San José del Cabo 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 Chicago Midway Airport to San José del Cabo that are best for you.

Fly from

Midway

Fly to

San José del Cabo

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-2:26 pm

1 stop19h 47m

San José del Cabo Los Cabos

Fri 7/11

8:10 am-7:16 pm

1 stop9h 06m

$500

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

Tue 7/15

6:00 am-11:22 am

1 stop7h 22m

San José del Cabo Los Cabos

Tue 7/22

12:27 pm-4:20 pm

1 stop25h 53m

$611

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

Fri 8/15

8:39 pm-4:46 pm

1 stop22h 07m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo 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 San José del Cabo

What is the cheapest month to book a flight from Chicago Midway Airport to San José del Cabo?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $437). Flying from Chicago Midway Airport to San José del Cabo 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 San José del Cabo by month

Plan your trip to San José del Cabo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José del Cabo 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 San José del Cabo when rainfall is around 0.0 in.

Temperature in San José del Cabo by month

Plan your trip to San José del Cabo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José del Cabo, 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 San José del Cabo

Get insights into the airlines that provide service to San José del Cabo. 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 San José del Cabo. Reviews last updated June 12, 2025.
Read through reviews of airlines operating flights from Chicago to San José del Cabo, such as Southwest, Delta and Aeromexico. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

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 San José del Cabo. 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 into for flights to San José del Cabo from Chicago Midway?

    Located just 6.6 mi from the city center, San José del Cabo Los Cabos is the airport most travelers will use when flying to San José del Cabo from Chicago Midway. Booking flights from Chicago Midway to Los Cabos (SJD) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • What are the cheapest airlines flying from Chicago Midway Airport to San José del Cabo round-trip?

    According to our current data, Delta ($400), Southwest ($430), and Volaris ($534) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Delta is 43% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Chicago Midway Airport to San José del Cabo are Delta ($167), Southwest ($208), and Volaris ($212).

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $437). Flying from Chicago Midway Airport to San José del Cabo 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 San José del Cabo

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

Discover the top airline that operate flights from Midway to San José del Cabo. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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