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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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$413
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$810
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
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Highest demand for flights based on searches. 7% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:39 pmMDW - SJD
1 stop12h 51mMultiple Airlines
Sat 5/178:22 amSJD - MDW
1 stop8h 44mMultiple Airlines
Deal found 3/26$413
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Fri 5/28:39 pmMDW - SJD
1 stop13h 08mVolaris
Tue 5/68:22 amSJD - MDW
1 stop8h 44mVolaris
Deal found 3/24$433
This Delta deal was found by Cheapflights users on 3/25. 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.
Sun 5/116:00 amMDW - SJD
2 stops14h 15mDelta
Wed 5/146:06 amSJD - MDW
2 stops13h 22mDelta
Deal found 3/25$505
This Southwest deal was found by Cheapflights users on 3/24. 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 4/69:10 amMDW - SJD
Nonstop5h 00mSouthwest
Sat 4/1212:55 pmSJD - MDW
1 stop8h 35mSouthwest
Deal found 3/24$543

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 March 26, 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

Sat 5/10

8:39 pm-7:30 am

1 stop12h 51m

San José del Cabo Los Cabos

Sat 5/17

8:22 am-7:06 pm

1 stop8h 44m

$413

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 5/2

8:39 pm-7:47 am

1 stop13h 08m

San José del Cabo Los Cabos

Tue 5/6

8:22 am-7:06 pm

1 stop8h 44m

$433

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 5/11

6:00 am-6:15 pm

2 stops14h 15m

San José del Cabo Los Cabos

Wed 5/14

6:06 am-9:28 pm

2 stops13h 22m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/6

9:10 am-12:10 pm

Nonstop5h 00m

San José del Cabo Los Cabos

Sat 4/12

12:55 pm-11:30 pm

1 stop8h 35m

$543

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 5/11

6:00 am-11:43 am

1 stop7h 43m

San José del Cabo Los Cabos

Wed 5/14

12:48 pm-5:36 pm

1 stop26h 48m

$717

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/1

6:40 am-7:47 am

3 stops27h 07m

$152

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 5/26

8:39 pm-7:47 am

1 stop13h 08m

$154

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 4/25

8:01 pm-10:56 am

1 stop16h 55m

$198

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 4/2

12:51 pm-9:22 pm

2 stops10h 31m

$233

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 5/9

6:00 am-11:43 am

1 stop7h 43m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 11 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José del Cabo flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

What is the cheapest time of day to fly from MDW to SJD?

Find hourly flight availability from Midway to San José del Cabo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 26, 2025.

When flying from Chicago Midway Airport to San José del Cabo, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 March 26, 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
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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
1,701 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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
1,173 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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.
Frontier
6.0
Okay
3,272 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

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, Volaris ($433), Delta ($505), and Southwest ($543) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Volaris is 40% 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 ($154), Frontier ($198), and Delta ($233).

  • 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

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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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$727FlexibilityNo cancel feeOn-time63%
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