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San José del Cabo

$152+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
1 adult, Economy
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Cheap 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 December 10, 2025.

This Delta deal was found by Cheapflights users on 12/8. 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 12/156:00 amMDW - SJD
1 stop7h 10mDelta
Thu 12/181:15 pmSJD - MDW
1 stop9h 32mDelta
Deal found 12/8$488
This Southwest deal was found by Cheapflights users on 12/8. 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 12/155:25 amMDW - SJD
1 stop10h 25mSouthwest
Thu 12/1811:50 amSJD - MDW
2 stops8h 25mSouthwest
Deal found 12/8$493
This Southwest deal was found by Cheapflights users on 12/9. 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 12/98:20 pmMDW - SJD
2 stops16h 50mSouthwest
Thu 1/82:35 pmSJD - MDW
1 stop7h 20mSouthwest
Deal found 12/9$508
This Delta deal was found by Cheapflights users on 12/9. 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 12/97:02 pmMDW - SJD
2 stops20h 08mDelta
Thu 1/89:35 amSJD - MDW
2 stops11h 32mDelta
Deal found 12/9$509
This Aeromexico deal was found by Cheapflights users on 12/8. 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 12/246:00 amMDW - SJD
1 stop9h 10mAeromexico
Wed 12/311:52 pmSJD - MDW
1 stop7h 30mAeromexico
Deal found 12/8$522
This Southwest deal was found by Cheapflights users on 12/9. 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 12/306:05 amMDW - SJD
1 stop7h 25mSouthwest
Wed 1/712:35 pmSJD - MDW
1 stop7h 40mSouthwest
Deal found 12/9$527
This Delta deal was found by Cheapflights users on 12/9. 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.
Sun 12/146:00 amMDW - SJD
1 stop7h 10mDelta
Sun 12/211:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 12/9$533
This Delta deal was found by Cheapflights users on 12/8. 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 12/246:00 amMDW - SJD
1 stop7h 47mDelta
Wed 12/311:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 12/8$556
This Delta deal was found by Cheapflights users on 12/9. 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 12/166:00 amMDW - SJD
1 stop7h 10mDelta
Mon 1/51:45 pmSJD - MDW
1 stop7h 22mDelta
Deal found 12/9$563

Find 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 December 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$443
(Expedia)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$1,293

Good round-trip deal

$580 or less
Provider with most accurate pricing for Chicago Midway-San José del Cabo Los Cabos flight deals.
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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
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One-way flight from Chicago Midway to San José del Cabo Los Cabos
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($216 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San José del Cabo Los Cabos.
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 December 10, 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

Wed 3/11

10:40 am-1:35 pm

Nonstop4h 55m

San José del Cabo Los Cabos

Wed 3/18

10:35 am-4:30 pm

Nonstop3h 55m

$485

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/2

5:05 am-11:40 am

1 stop7h 35m

San José del Cabo Los Cabos

Tue 2/17

2:05 pm-12:25 am

1 stop9h 20m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 1/21

6:00 am-5:41 pm

2 stops12h 41m

San José del Cabo Los Cabos

Tue 1/27

1:45 pm-10:22 pm

1 stop7h 37m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 2/18

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Wed 2/25

6:05 am-10:42 pm

2 stops15h 37m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

6:40 pm-8:40 am

2 stops15h 00m

San José del Cabo Los Cabos

Fri 3/6

4:56 pm-8:53 am

2 stops14h 57m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/7

5:38 pm-7:45 am

2 stops16h 07m

San José del Cabo Los Cabos

Tue 4/14

12:15 pm-9:45 pm

1 stop7h 30m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/2

5:00 am-11:05 am

1 stop7h 05m

San José del Cabo Los Cabos

Sun 3/8

1:20 pm-7:15 pm

Nonstop3h 55m

$535

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/7

9:38 am-8:35 pm

3 stops35h 57m

$200

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/15

6:00 am-12:10 pm

1 stop7h 10m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 17 results
1
2

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 December.
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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $471). Flying from Chicago Midway Airport to San José del Cabo in February is currently the most expensive (average of $800). 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 December 10, 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
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $485, Southwest can have you in San José del Cabo from Chicago Midway Airport in 4h 55m. 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 26% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from Chicago Midway Airport to San José del Cabo?

    On average you can expect to pay $585 for a flight from Chicago Midway Airport to San José del Cabo. The cheapest flight overall is $467 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $465.

  • 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $471). Flying from Chicago Midway Airport to San José del Cabo in February is currently the most expensive (average of $800). 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 December 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$707FlexibilityNo cancel feeOn-time63%

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