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$199+ Cheap flights from San José del Cabo (SJD) to Midway (MDW)

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
ene. 29 — feb. 51
jue. 1/29
jue. 2/5
1 adult, Economy
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Cheap flight deals from San José del Cabo to Midway

Cheapest flights from San José del Cabo to Midway
Explore the most affordable flight options available from San José del Cabo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 30, 2025.

This Delta deal was found by Cheapflights users on 12/28. 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.
lun. 12/299:40 amSJD - MDW
2 stops11h 42mDelta
vie. 1/26:00 amMDW - SJD
1 stop7h 47mDelta
Deal found 12/28$959

Find flight deals from San José del Cabo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José del Cabo (SJD) to Midway (MDW). 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 diciembre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$378
(Aeromexico)

One-way from

$199
(Priceline)

Popular in

May

Cheapest in

September

Average price

$653
Provider with most accurate pricing for San José del Cabo Los Cabos-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San José del Cabo Los Cabos-Chicago Midway flights.
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From San José del Cabo Los Cabos to Chicago Midway
Search Deals
One-way flight from San José del Cabo Los Cabos to Chicago Midway
Search Deals
Highest demand for flights based on searches. 40% potential increase in price ($445 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($94 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Midway 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 diciembre 30, 2025.
Use the filters below to find and compare flights from San José del Cabo to Chicago Midway Airport that are best for you.

Fly from

San José del Cabo

Fly to

Midway

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 2/13

6:05 am-10:31 pm

2 stops15h 26m

Chicago Midway

lun. 2/16

12:45 pm-9:31 am

2 stops21h 46m

$378

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 1/14

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

dom. 1/18

6:45 am-2:09 pm

1 stop8h 24m

$421

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

lun. 1/12

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

sáb. 1/17

5:31 pm-8:40 am

2 stops16h 09m

$509

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 2/18

4:56 pm-8:54 am

2 stops14h 58m

$240

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 2/6

1:45 pm-10:22 pm

1 stop7h 37m

$240

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 1/23

1:45 pm-10:22 pm

1 stop7h 37m

$241

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 2/4

1:45 pm-10:22 pm

1 stop7h 37m

$241

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

jue. 2/19

4:56 pm-9:06 am

2 stops15h 10m

$241

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

vie. 1/30

1:45 pm-10:22 pm

1 stop7h 37m

$241

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

mié. 1/28

9:35 am-10:22 pm

2 stops11h 47m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 14 results
1
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Compare providers for flights from San José del Cabo to Midway

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 San José del Cabo to Midway in December.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 San José del Cabo-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San José del Cabo-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from San José del Cabo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José del Cabo-Chicago Midway Airport 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 San José del Cabo-Chicago Midway Airport 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 San José del Cabo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San José del Cabo 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 San José del Cabo to Chicago Midway Airport

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

Find hourly flight availability from San José del Cabo to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 30, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from San José del Cabo to Midway. 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 from for flights from San José del Cabo to Chicago Midway?

    For a flight from San José del Cabo to Chicago Midway, you will be flying from Los Cabos. San José del Cabo Los Cabos (SJD) is just 6.6 mi from the center of the city. Los Cabos is the only San José del Cabo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from San José del Cabo Los Cabos on a regular basis.

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

    Aeromexico and Delta can get you from San José del Cabo to Chicago Midway Airport in just under 7h 22m. Your travel time can differ by up to 8h 04m. There are 1804 mi between San José del Cabo and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from San José del Cabo to Midway that include hotel bookings?

    Yes. In addition to deals on San José del Cabo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José del Cabo to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José del Cabo to Midway.

  • Can I find deals for business class flights from San José del Cabo to Midway?

    Yes. Cheapflights offers flight deals from San José del Cabo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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