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San José del Cabo

$165+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$436
(Southwest)

One-way from

$165
(Mytrip)

Popular in

November

Cheapest in

October

Average price

$548
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. 1% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:00 amMDW - SJD
1 stop9h 10mSouthwest
Tue 10/711:15 amSJD - MDW
2 stops10h 20mSouthwest
Deal found 8/16$436
This Delta deal was found by Cheapflights users on 8/16. 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.
Wed 9/176:00 amMDW - SJD
2 stops10h 55mDelta
Sat 9/206:01 amSJD - MDW
2 stops13h 09mDelta
Deal found 8/16$452
This Southwest deal was found by Cheapflights users on 8/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:15 amMDW - SJD
1 stop7h 05mSouthwest
Wed 11/191:25 pmSJD - MDW
1 stop7h 50mSouthwest
Deal found 8/16$457
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:20 amMDW - SJD
2 stops30h 00mDelta
Thu 11/61:47 pmSJD - MDW
1 stop7h 27mDelta
Deal found 8/17$481
This Southwest deal was found by Cheapflights users on 8/17. 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.
Mon 9/297:50 amMDW - SJD
1 stop7h 00mSouthwest
Sat 10/41:50 pmSJD - MDW
2 stops16h 40mSouthwest
Deal found 8/17$487
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:00 amMDW - SJD
1 stop7h 10mSouthwest
Sun 12/141:25 pmSJD - MDW
1 stop11h 05mSouthwest
Deal found 8/18$492
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sun 9/215:30 amMDW - SJD
2 stops9h 40mSouthwest
Wed 9/2412:40 pmSJD - MDW
1 stop8h 40mSouthwest
Deal found 8/17$495
This Southwest deal was found by Cheapflights users on 8/17. 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.
Wed 11/55:25 amMDW - SJD
1 stop10h 25mSouthwest
Sat 11/812:55 pmSJD - MDW
2 stops18h 55mSouthwest
Deal found 8/17$497
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:10 pmMDW - SJD
2 stops20h 10mDelta
Mon 11/33:25 pmSJD - MDW
2 stops20h 43mDelta
Deal found 8/17$501
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:00 pmMDW - SJD
2 stops25h 30mDelta
Sat 11/224:30 pmSJD - MDW
2 stops15h 16mDelta
Deal found 8/17$502

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 August 18, 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 10/27

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Tue 11/4

3:25 pm-8:40 am

2 stops16h 15m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/28

6:00 am-1:10 pm

1 stop9h 10m

San José del Cabo Los Cabos

Tue 10/7

11:15 am-11:35 pm

2 stops10h 20m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/28

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Tue 11/4

3:25 pm-8:40 am

2 stops16h 15m

$436

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/12

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sun 11/16

1:17 pm-9:44 pm

1 stop7h 27m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 10/18

5:00 am-10:40 am

1 stop7h 40m

San José del Cabo Los Cabos

Tue 10/21

11:15 am-9:20 pm

1 stop8h 05m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 9/27

6:00 am-2:30 pm

2 stops10h 30m

San José del Cabo Los Cabos

Thu 10/2

6:00 am-9:36 pm

2 stops13h 36m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 10/17

6:50 am-1:25 pm

1 stop8h 35m

San José del Cabo Los Cabos

Fri 10/24

12:50 pm-12:10 am

1 stop9h 20m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 9/17

6:00 am-2:55 pm

2 stops10h 55m

San José del Cabo Los Cabos

Sat 9/20

6:01 am-9:10 pm

2 stops13h 09m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/29

7:50 am-12:50 pm

1 stop7h 00m

San José del Cabo Los Cabos

Sat 10/4

1:35 pm-10:25 pm

1 stop6h 50m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 11/18

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Mon 11/24

1:17 pm-9:44 pm

1 stop7h 27m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 19 results
1
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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.

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 August 18, 2025.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Chicago Midway Airport to San José del Cabo?

    For as low as $436, Delta can have you in San José del Cabo from Chicago Midway Airport in 7h 42m. The distance between Chicago Midway Airport and San José del Cabo is about 1804 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to San José del Cabo round-trip?

    According to our current data, Southwest ($545), offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Southwest is 22% 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 Volaris ($165), Aeromexico ($180), and Delta ($180).

  • 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
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O'Hare Intl to Loreto 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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