HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José del Cabo

$158+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
abr. 20 — abr. 271
dom. 4/20
dom. 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to San José del Cabo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 abril 15, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$407
(Aeromexico)

One-way from

$158
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$700
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.
Search Deals
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. 8% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 abril 15, 2025.

This Aeromexico deal was found by Cheapflights users on 4/15. 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.
dom. 9/76:00 amMDW - SJD
1 stop7h 30mAeromexico
vie. 9/126:01 amSJD - MDW
2 stops13h 43mAeromexico
Deal found 4/15$407
This Delta deal was found by Cheapflights users on 4/13. 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.
jue. 9/256:00 amMDW - SJD
2 stops14h 01mDelta
mar. 9/306:01 amSJD - MDW
2 stops13h 43mDelta
Deal found 4/13$447
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
dom. 5/118:39 pmMDW - SJD
1 stop18h 01mMultiple Airlines
sáb. 5/248:22 amSJD - MDW
1 stop8h 44mMultiple Airlines
Deal found 4/15$481
This Southwest deal was found by Cheapflights users on 4/13. 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.
vie. 6/205:15 amMDW - SJD
1 stop5h 50mSouthwest
mar. 6/241:15 pmSJD - MDW
1 stop9h 40mSouthwest
Deal found 4/13$516
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
mar. 9/28:39 pmMDW - SJD
1 stop13h 14mVolaris
lun. 9/88:29 amSJD - MDW
1 stop8h 47mVolaris
Deal found 4/14$538

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 abril 15, 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

dom. 9/7

6:00 am-11:30 am

1 stop7h 30m

San José del Cabo Los Cabos

vie. 9/12

6:01 am-9:44 pm

2 stops13h 43m

$407

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

jue. 9/25

6:00 am-6:01 pm

2 stops14h 01m

San José del Cabo Los Cabos

mar. 9/30

6:01 am-9:44 pm

2 stops13h 43m

$447

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 5/11

8:39 pm-12:40 pm

1 stop18h 01m

San José del Cabo Los Cabos

sáb. 5/24

8:22 am-7:06 pm

1 stop8h 44m

$481

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 6/20

5:15 am-9:05 am

1 stop5h 50m

San José del Cabo Los Cabos

mar. 6/24

1:15 pm-12:55 am

1 stop9h 40m

$516

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 9/2

8:39 pm-7:53 am

1 stop13h 14m

San José del Cabo Los Cabos

lun. 9/8

8:29 am-7:16 pm

1 stop8h 47m

$538

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 5/12

2:45 pm-8:40 am

3 stops19h 55m

$158

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 5/30

6:00 am-11:43 am

1 stop7h 43m

$221

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 6/15

6:00 am-10:40 am

1 stop6h 40m

$251

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 10/8

8:39 pm-7:53 am

1 stop13h 14m

$260

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 10/8

1:05 pm-9:51 pm

2 stops10h 46m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-San José del Cabo flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 $437). Flying from Chicago Midway Airport to San José del Cabo in June is currently the most expensive (average of $560). 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 abril 15, 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
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Volaris
6.7
Okay
1,172 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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, Aeromexico ($407), Delta ($447), and Southwest ($516) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Aeromexico 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 ($221), Southwest ($251), and Volaris ($260).

  • 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 June is currently the most expensive (average of $560). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 abril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.