$244+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Sep 13 — Sep 201
Round-trip
1 adult, Economy
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Find cheap flights from San José del Cabo to Midway 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
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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 San José del Cabo to Midway
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Cheapest flights from San José del Cabo to MidwayExplore 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 August 14, 2026.
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 August 14, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Fri 10/3011:05 am -
1 stop8h 45m
Fri 11/65:15 am -
1 stop8h 55m
Deal found 8/10![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/2412:12 pm -
1 stop8h 32m
Sun 9/276:05 am -
1 stop7h 02m
Deal found 8/11![Delta logo]()
$658
This Delta deal was found by Cheapflights users on 8/10. 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 11/31:25 pm -
1 stop8h 08m
Mon 11/96:00 am -
2 stops13h 34m
Deal found 8/10![Delta logo]()
$662
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 9/2410:40 am -
2 stops10h 45m
Sun 9/276:05 am -
2 stops9h 05m
Deal found 8/11![Southwest logo]()
$726
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/1211:35 am -
1 stop8h 45m
Wed 9/166:00 am -
2 stops8h 50m
Deal found 8/12![Southwest logo]()
$757
This Delta deal was found by Cheapflights users on 8/12. 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 9/2712:12 pm -
1 stop8h 32m
Sun 10/46:05 am -
1 stop7h 02m
Deal found 8/12![Delta logo]()
$777
This Southwest deal was found by Cheapflights users on 8/12. 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 8/2611:40 am -
1 stop9h 30m
Sat 8/297:20 am -
1 stop6h 55m
Deal found 8/12![Southwest logo]()
$838
Best flights from San José del Cabo to MidwayDiscover carefully curated flight deals from San José del Cabo to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
Discover carefully curated flight deals from San José del Cabo to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Fri 10/3011:05 am -
1 stop8h 45m
Fri 11/65:15 am -
1 stop8h 55m
Deal found 8/10![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/2412:12 pm -
1 stop8h 32m
Sun 9/276:05 am -
1 stop7h 02m
Deal found 8/11![Delta logo]()
$658
This Delta deal was found by Cheapflights users on 8/10. 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 11/31:25 pm -
1 stop8h 08m
Mon 11/96:00 am -
2 stops13h 34m
Deal found 8/10![Delta logo]()
$662
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/1211:35 am -
1 stop8h 45m
Wed 9/166:00 am -
2 stops8h 50m
Deal found 8/12![Southwest logo]()
$757
This Delta deal was found by Cheapflights users on 8/12. 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 9/2712:12 pm -
1 stop8h 32m
Sun 10/46:05 am -
1 stop7h 02m
Deal found 8/12![Delta logo]()
$777
This Southwest deal was found by Cheapflights users on 8/12. 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 8/2611:40 am -
2 stops8h 10m
Sat 8/297:20 am -
1 stop6h 55m
Deal found 8/12![Southwest logo]()
$843
Last-minute flights from San José del Cabo to MidwayDiscover last-minute flight deals from San José del Cabo to Midway. Data last updated August 14, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated August 14, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/12. 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 8/2611:40 am -
1 stop9h 30m
Sat 8/297:20 am -
1 stop6h 55m
Deal found 8/12![Southwest logo]()
$838
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/1211:35 am -
1 stop8h 45m
Wed 9/166:00 am -
2 stops8h 50m
Deal found 8/12![Southwest logo]()
$757
This Delta deal was found by Cheapflights users on 8/11. 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.
Thu 9/2412:12 pm -
1 stop8h 32m
Sun 9/276:05 am -
1 stop7h 02m
Deal found 8/11![Delta logo]()
$658
This Southwest deal was found by Cheapflights users on 8/11. 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.
Thu 9/2410:40 am -
2 stops10h 45m
Sun 9/276:05 am -
2 stops9h 05m
Deal found 8/11![Southwest logo]()
$726
This Delta deal was found by Cheapflights users on 8/12. 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 9/2712:12 pm -
1 stop8h 32m
Sun 10/46:05 am -
1 stop7h 02m
Deal found 8/12![Delta logo]()
$777
This Southwest deal was found by Cheapflights users on 8/12. 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 9/272:05 pm -
2 stops13h 35m
Sun 10/45:00 am -
2 stops10h 15m
Deal found 8/12![Southwest logo]()
$897
One-way flights from San José del Cabo to MidwaySearch for one-way flight options from San José del Cabo to Midway. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
Search for one-way flight options from San José del Cabo to Midway. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sun 9/137:47 pm -
3 stops43h 59m
Deal found 8/12![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:18 pm -
1 stop22h 29m
Deal found 8/13![Volaris logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sun 9/1312:06 pm -
1 stop28h 58m
Deal found 8/12![Volaris logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Tue 9/1512:06 pm -
1 stop28h 58m
Deal found 8/12![Volaris logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Thu 9/107:47 pm -
2 stops38h 12m
Deal found 8/12![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:30 pm -
2 stops22h 18m
Deal found 8/13![Volaris logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/123:36 pm -
1 stop25h 28m
Deal found 8/12![Volaris logo]()
$265
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 August 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $610 (Southwest) |
One-way from | $244 (Kiwi.com) |
Popular in | August |
Cheapest in | September |
Average price | $795 |
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 August 14, 2026.
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
Fly to
Route
Depart
Return
Cheapest round-trip
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 10/30
11:05 am-9:50 pm
1 stop8h 45m
Chicago Midway
Fri 11/6
5:15 am-1:10 pm
1 stop8h 55m
$610
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 9/24
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Sun 9/27
6:05 am-11:07 am
1 stop7h 02m
$658
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Tue 11/3
1:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Mon 11/9
6:00 am-6:34 pm
2 stops13h 34m
$662
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sat 9/12
11:35 am-10:20 pm
1 stop8h 45m
Chicago Midway
Wed 9/16
6:00 am-12:50 pm
2 stops8h 50m
$757
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sun 9/27
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Sun 10/4
6:05 am-11:07 am
1 stop7h 02m
$777
Quickest round-trip
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 8/26
11:40 am-9:50 pm
2 stops8h 10m
Chicago Midway
Sat 8/29
7:20 am-12:15 pm
1 stop6h 55m
$843
Cheapest one-way
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 10/9
12:15 pm-12:25 am
1 stop10h 10m
$276
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 11/13
2:45 pm-1:05 am
2 stops9h 20m
$276
Quickest one-way
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 9/10
1:45 pm-10:20 pm
1 stop6h 35m
$276
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 9/18
10:40 am-10:20 pm
1 stop9h 40m
$276
Showing 1-10 of 14 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on San José del Cabo-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José del Cabo-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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.
SJD-MDW
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.
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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