$286+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Sep 25 — Oct 21
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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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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:12 pm -
1 stop8h 32m
Mon 10/56:05 am -
1 stop7h 02m
Deal found 8/24![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 8/22. 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 10/11:30 pm -
1 stop6h 50m
Sun 10/45:25 am -
1 stop7h 40m
Deal found 8/22![Southwest logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/121:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26![Multiple Airlines logo]()
$572
This Southwest deal was found by Cheapflights users on 8/22. 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 10/11:30 pm -
1 stop6h 50m
Mon 10/55:25 am -
1 stop10h 15m
Deal found 8/22![Southwest logo]()
$576
This Southwest deal was found by Cheapflights users on 8/24. 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.
Tue 10/271:30 pm -
1 stop7h 40m
Fri 10/305:15 am -
2 stops10h 25m
Deal found 8/24![Southwest logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sun 9/131:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26![Multiple Airlines logo]()
$588
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/92:15 pm -
1 stop8h 55m
Sat 10/175:10 am -
1 stop7h 30m
Deal found 8/25![Southwest logo]()
$596
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 26, 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 26, 2026.
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:12 pm -
1 stop8h 32m
Mon 10/56:05 am -
1 stop7h 02m
Deal found 8/24![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 8/22. 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 10/11:30 pm -
1 stop6h 50m
Sun 10/45:25 am -
1 stop7h 40m
Deal found 8/22![Southwest logo]()
$553
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/129:04 am -
3 stops31h 01m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26![Multiple Airlines logo]()
$630
This Mytrip deal was found by Cheapflights users on 8/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:10 pm -
3 stops25h 54m
Wed 9/168:23 pm -
2 stops21h 36m
Deal found 8/26![Volaris logo]()
$673
This Southwest deal was found by Cheapflights users on 8/22. 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 10/11:30 pm -
1 stop6h 50m
Mon 10/55:25 am -
1 stop10h 15m
Deal found 8/22![Southwest logo]()
$576
This Delta deal was found by Cheapflights users on 8/25. 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.
Tue 9/2912:12 pm -
1 stop8h 32m
Fri 10/212:35 pm -
2 stops11h 55m
Deal found 8/25![Delta logo]()
$605
This Southwest deal was found by Cheapflights users on 8/24. 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.
Tue 10/271:30 pm -
1 stop7h 40m
Fri 10/305:15 am -
2 stops10h 25m
Deal found 8/24![Southwest logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 11/277:27 am -
1 stop8h 20m
Tue 12/16:20 pm -
2 stops22h 48m
Deal found 8/23![Multiple Airlines logo]()
$688
This Southwest deal was found by Cheapflights users on 8/24. 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.
Fri 10/210:45 am -
2 stops10h 20m
Mon 10/510:55 pm -
2 stops14h 25m
Deal found 8/24![Southwest logo]()
$592
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 26, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated August 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:17 am -
2 stops11h 19m
Tue 9/86:05 am -
1 stop7h 02m
Deal found 8/24![Delta logo]()
$750
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/121:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26![Multiple Airlines logo]()
$572
This Mytrip deal was found by Cheapflights users on 8/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:10 pm -
3 stops25h 54m
Wed 9/168:23 pm -
2 stops21h 36m
Deal found 8/25![Volaris logo]()
$662
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sun 9/131:12 pm -
1 stop27h 52m
Wed 9/168:23 pm -
1 stop18h 03m
Deal found 8/26![Multiple Airlines logo]()
$588
This Mytrip deal was found by Cheapflights users on 8/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:47 pm -
2 stops21h 17m
Wed 9/168:23 pm -
2 stops15h 46m
Deal found 8/26![Volaris logo]()
$707
This Aeromexico deal was found by Cheapflights users on 8/25. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:28 pm -
2 stops26h 16m
Fri 10/26:05 am -
2 stops18h 25m
Deal found 8/25![Aeromexico logo]()
$585
This Delta deal was found by Cheapflights users on 8/25. 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.
Tue 9/2912:12 pm -
1 stop8h 32m
Fri 10/212:35 pm -
2 stops11h 55m
Deal found 8/25![Delta logo]()
$605
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 26, 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 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:12 pm -
1 stop27h 52m
Deal found 8/25![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 2/219:29 pm -
1 stop18h 18m
Deal found 8/22![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/223:36 pm -
1 stop25h 28m
Deal found 8/23![Volaris logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 9/2412:06 pm -
1 stop28h 58m
Deal found 8/23![Volaris logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/153:36 pm -
1 stop25h 28m
Deal found 8/22![Volaris logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 8/23![Volaris logo]()
$295
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 9/2312:12 pm -
1 stop8h 32m
Deal found 8/25![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 8/21. 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 11/201:30 pm -
1 stop9h 25m
Deal found 8/21![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 2/201:47 pm -
1 stop26h 00m
Deal found 8/23![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Mon 11/237:27 am -
1 stop8h 20m
Deal found 8/21![Multiple Airlines logo]()
$301
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 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $515 (Delta) |
One-way from | $286 (Kiwi.com) |
Popular in | August |
Cheapest in | December |
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 7,457,451 searches. Data last updated August 26, 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 10/2
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Mon 10/5
6:05 am-11:07 am
1 stop7h 02m
$515
Quickest round-trip
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 10/1
1:30 pm-10:20 pm
1 stop6h 50m
Chicago Midway
Sun 10/4
5:25 am-11:05 am
1 stop7h 40m
$553
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 10/1
1:30 pm-10:20 pm
1 stop6h 50m
Chicago Midway
Mon 10/5
5:25 am-1:40 pm
1 stop10h 15m
$576
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Tue 10/27
1:30 pm-11:10 pm
1 stop7h 40m
Chicago Midway
Fri 10/30
5:15 am-1:40 pm
2 stops10h 25m
$585
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 10/2
10:45 am-11:05 pm
2 stops10h 20m
Chicago Midway
Mon 10/5
10:55 pm-11:20 am
2 stops14h 25m
$592
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Tue 9/29
12:12 pm-10:44 pm
1 stop8h 32m
Chicago Midway
Fri 10/2
12:35 pm-10:30 pm
2 stops11h 55m
$605
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sat 9/12
9:04 am-6:05 pm
3 stops31h 01m
Chicago Midway
Wed 9/16
8:23 pm-12:26 pm
1 stop18h 03m
$630
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Sat 9/12
3:10 pm-7:04 pm
3 stops25h 54m
Chicago Midway
Wed 9/16
8:23 pm-3:59 pm
2 stops21h 36m
$673
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 11/27
7:27 am-4:47 pm
1 stop8h 20m
Chicago Midway
Tue 12/1
6:20 pm-4:08 pm
2 stops22h 48m
$688
Cheapest one-way
Quickest one-way
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 2/17
1:30 pm-10:10 pm
1 stop7h 40m
$297
Showing 1-10 of 18 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?
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