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San José del Cabo

$159+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Delta deal was found by Cheapflights users on 10/25. 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.
Tue 11/186:00 amMDW - SJD
1 stop7h 10mDelta
Mon 11/249:32 amSJD - MDW
2 stops13h 08mDelta
Deal found 10/25$423
This Delta deal was found by Cheapflights users on 10/26. 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 12/2211:48 amMDW - SJD
2 stops21h 57mDelta
Tue 12/309:40 amSJD - MDW
2 stops22h 25mDelta
Deal found 10/26$428
This Delta deal was found by Cheapflights users on 10/26. 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 11/76:00 amMDW - SJD
1 stop7h 42mDelta
Tue 11/119:32 amSJD - MDW
2 stops13h 08mDelta
Deal found 10/26$430
This Southwest deal was found by Cheapflights users on 10/25. 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 11/25:10 amMDW - SJD
1 stop9h 35mSouthwest
Thu 11/612:35 pmSJD - MDW
1 stop9h 45mSouthwest
Deal found 10/25$440
This Southwest deal was found by Cheapflights users on 10/25. 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.
Tue 11/115:00 amMDW - SJD
2 stops9h 10mSouthwest
Sat 11/1512:00 pmSJD - MDW
1 stop7h 35mSouthwest
Deal found 10/25$455
This Southwest deal was found by Cheapflights users on 10/25. 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 12/15:25 amMDW - SJD
2 stops9h 20mSouthwest
Fri 12/51:05 pmSJD - MDW
1 stop6h 50mSouthwest
Deal found 10/25$463
This Southwest deal was found by Cheapflights users on 10/26. 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 11/57:00 amMDW - SJD
1 stop7h 10mSouthwest
Wed 11/122:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 10/26$465
This Delta deal was found by Cheapflights users on 10/26. 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 11/196:00 amMDW - SJD
1 stop7h 10mDelta
Mon 11/241:15 pmSJD - MDW
1 stop9h 25mDelta
Deal found 10/26$467
This Delta deal was found by Cheapflights users on 10/26. 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 12/2211:48 amMDW - SJD
2 stops21h 57mDelta
Sun 12/2812:38 pmSJD - MDW
2 stops22h 20mDelta
Deal found 10/26$473
This Delta deal was found by Cheapflights users on 10/26. 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 10/316:00 amMDW - SJD
1 stop7h 42mDelta
Fri 11/71:47 pmSJD - MDW
1 stop7h 27mDelta
Deal found 10/26$490

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$159
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$471
Provider with most accurate pricing for Chicago Midway-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San José del Cabo Los Cabos flights.
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From Chicago Midway to San José del Cabo Los Cabos
Search Deals
One-way flight from Chicago Midway to San José del Cabo Los Cabos
Search Deals
Highest demand for flights based on searches. 32% potential increase in price ($388 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($109 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 27, 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

Tue 11/18

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Mon 11/24

9:32 am-11:40 pm

2 stops13h 08m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/22

11:48 am-8:45 am

2 stops21h 57m

San José del Cabo Los Cabos

Wed 12/31

3:15 pm-9:05 am

1 stop16h 50m

$428

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/22

11:48 am-8:45 am

2 stops21h 57m

San José del Cabo Los Cabos

Tue 12/30

9:40 am-9:05 am

2 stops22h 25m

$428

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/10

5:31 pm-8:40 am

2 stops16h 09m

San José del Cabo Los Cabos

Sat 1/31

6:05 am-10:26 pm

2 stops15h 21m

$477

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/28

4:30 pm-8:45 am

2 stops17h 15m

San José del Cabo Los Cabos

Wed 3/11

12:40 pm-9:46 pm

1 stop7h 06m

$479

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/28

10:35 am-8:45 am

2 stops23h 10m

San José del Cabo Los Cabos

Tue 3/10

8:40 am-9:46 pm

2 stops11h 06m

$479

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/21

5:10 am-3:25 pm

2 stops11h 15m

San José del Cabo Los Cabos

Tue 2/24

12:35 pm-9:15 pm

1 stop7h 40m

$512

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/4

5:15 am-2:50 pm

2 stops10h 35m

San José del Cabo Los Cabos

Wed 1/7

2:20 pm-10:50 pm

1 stop7h 30m

$517

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/15

6:20 am-12:00 pm

1 stop6h 40m

San José del Cabo Los Cabos

Mon 11/17

11:50 am-10:10 pm

1 stop9h 20m

$545

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 12/23

6:00 am-2:10 pm

1 stop9h 10m

San José del Cabo Los Cabos

Mon 12/29

1:52 pm-10:22 pm

1 stop7h 30m

$547

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 21 results
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Compare providers for flights from Midway to San José del Cabo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San José del Cabo in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San José del Cabo flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-San José del Cabo flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José del Cabo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José del Cabo flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San José del Cabo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $275). Flying from Chicago Midway Airport to San José del Cabo in February is currently the most expensive (average of $793). 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 October 27, 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
4,235 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $423, Delta can have you in San José del Cabo from Chicago Midway Airport in 7h 10m. The distance between Chicago Midway Airport and San José del Cabo is about 1804 mi.

  • 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 31% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 $275). Flying from Chicago Midway Airport to San José del Cabo in February is currently the most expensive (average of $793). 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
Midway to La Paz flights
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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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