$288+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Jun 21 — Jun 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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 San José del Cabo to Midway
Cheapest
Best
Last-minute
One-way
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 May 22, 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 May 22, 2026.
This Delta deal was found by Cheapflights users on 5/20. 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 8/1412:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Mon 8/176:05 am
MDW
- SJD
2 stops13h 36m
Delta
Deal found 5/20![Delta logo]()
$533
This Volaris deal was found by Cheapflights users on 5/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Thu 8/68:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/17![Volaris logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/256:50 am
SJD
- MDW
1 stop10h 44m
Multiple Airlines
Sun 7/58:23 pm
MDW
- SJD
1 stop18h 02m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 5/22. 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 9/131:12 pm
SJD
- MDW
1 stop27h 52m
Multiple Airlines
Fri 9/188:23 pm
MDW
- SJD
1 stop18h 03m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 5/20. 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 10/811:57 am
SJD
- MDW
1 stop7h 48m
Delta
Tue 10/136:00 am
MDW
- SJD
1 stop6h 55m
Delta
Deal found 5/20![Delta logo]()
$595
This Delta deal was found by Cheapflights users on 5/18. 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 7/3112:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Wed 8/56:05 am
MDW
- SJD
1 stop7h 02m
Delta
Deal found 5/18![Delta logo]()
$602
This Southwest deal was found by Cheapflights users on 5/20. 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 10/811:50 am
SJD
- MDW
1 stop7h 35m
Southwest
Tue 10/136:00 am
MDW
- SJD
2 stops9h 40m
Southwest
Deal found 5/20![Southwest logo]()
$604
This Delta deal was found by Cheapflights users on 5/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Fri 7/246:00 am
MDW
- SJD
2 stops11h 37m
Delta
Deal found 5/22![Delta logo]()
$620
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 May 22, 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 May 22, 2026.
This Delta deal was found by Cheapflights users on 5/20. 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 8/216:04 am
SJD
- MDW
2 stops14h 32m
Delta
Mon 8/246:05 am
MDW
- SJD
2 stops13h 36m
Delta
Deal found 5/20![Delta logo]()
$533
This Volaris deal was found by Cheapflights users on 5/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Thu 8/68:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/17![Volaris logo]()
$557
This Southwest deal was found by Cheapflights users on 5/20. 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 10/812:15 pm
SJD
- MDW
2 stops10h 30m
Southwest
Tue 10/136:00 am
MDW
- SJD
2 stops9h 40m
Southwest
Deal found 5/20![Southwest logo]()
$638
This Delta deal was found by Cheapflights users on 5/20. 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 8/146:04 am
SJD
- MDW
2 stops14h 32m
Delta
Mon 8/176:05 am
MDW
- SJD
2 stops13h 36m
Delta
Deal found 5/20![Delta logo]()
$533
This Southwest deal was found by Cheapflights users on 5/19. 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 6/2610:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Mon 6/295:20 am
MDW
- SJD
1 stop6h 25m
Southwest
Deal found 5/19![Southwest logo]()
$659
This Delta deal was found by Cheapflights users on 5/18. 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 7/3112:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Wed 8/56:05 am
MDW
- SJD
2 stops14h 37m
Delta
Deal found 5/18![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 5/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Fri 7/246:00 am
MDW
- SJD
2 stops11h 37m
Delta
Deal found 5/22![Delta logo]()
$620
Last-minute flights from San José del Cabo to MidwayDiscover last-minute flight deals from San José del Cabo to Midway. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated May 22, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/21. 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.
Sat 5/2311:35 am
SJD
- MDW
1 stop9h 10m
Southwest
Tue 6/237:00 am
MDW
- SJD
1 stop7h 55m
Southwest
Deal found 5/21![Southwest logo]()
$778
This WestJet deal was found by Cheapflights users on 5/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:10 pm
SJD
- MDW
2 stops24h 23m
WestJet
Tue 6/239:54 am
MDW
- SJD
2 stops29h 26m
WestJet
Deal found 5/21![WestJet logo]()
$2,486
This Southwest deal was found by Cheapflights users on 5/22. 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.
Mon 6/812:55 pm
SJD
- MDW
1 stop9h 15m
Southwest
Fri 6/126:40 am
MDW
- SJD
1 stop7h 30m
Southwest
Deal found 5/22![Southwest logo]()
$784
This Southwest deal was found by Cheapflights users on 5/18. 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.
Mon 6/1511:15 am
SJD
- MDW
1 stop11h 20m
Southwest
Mon 6/225:20 am
MDW
- SJD
1 stop6h 25m
Southwest
Deal found 5/18![Southwest logo]()
$696
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/256:50 am
SJD
- MDW
1 stop10h 44m
Multiple Airlines
Sun 7/58:23 pm
MDW
- SJD
1 stop18h 02m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$577
This Southwest deal was found by Cheapflights users on 5/18. 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 6/2510:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Sun 7/55:00 am
MDW
- SJD
2 stops10h 10m
Southwest
Deal found 5/18![Southwest logo]()
$674
This Delta deal was found by Cheapflights users on 5/19. 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 6/2612:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Mon 6/296:00 am
MDW
- SJD
1 stop7h 25m
Delta
Deal found 5/19![Delta logo]()
$633
This Southwest deal was found by Cheapflights users on 5/19. 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 6/2610:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Mon 6/295:20 am
MDW
- SJD
1 stop6h 25m
Southwest
Deal found 5/19![Southwest logo]()
$659
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 May 22, 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 May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/116:50 am
SJD
- MDW
1 stop10h 44m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 5/21. 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.
Tue 7/71:10 pm
SJD
- MDW
1 stop27h 54m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 5/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/21![Delta logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/114:49 pm
SJD
- MDW
2 stops24h 15m
Volaris
Deal found 5/19![Volaris logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/21. 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.
Tue 7/77:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 5/21![Volaris logo]()
$324
This Super.com deal was found by Cheapflights users on 5/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/198:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 5/17![Volaris logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/286:50 am
SJD
- MDW
1 stop10h 14m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/2811:29 am
SJD
- MDW
2 stops29h 35m
Volaris
Deal found 5/19![Volaris logo]()
$362
This Southwest deal was found by Cheapflights users on 5/20. 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 7/122:25 pm
SJD
- MDW
1 stop13h 20m
Southwest
Deal found 5/20![Southwest logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 5/22. 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 7/128:25 am
SJD
- MDW
3 stops24h 42m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 5/22. 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 7/127:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 5/22![Volaris logo]()
$397
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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $533 (Delta) |
One-way from | $288 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $341 |
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 May 22, 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 - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 8/21
6:04 am-10:36 pm
2 stops14h 32m
Chicago Midway
Mon 8/24
6:05 am-5:41 pm
2 stops13h 36m
$533
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 8/14
6:04 am-10:36 pm
2 stops14h 32m
Chicago Midway
Mon 8/17
6:05 am-5:41 pm
2 stops13h 36m
$533
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 7/31
8:50 am-7:04 pm
1 stop8h 14m
Chicago Midway
Thu 8/6
8:49 pm-8:16 am
1 stop13h 27m
$557
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 7/31
12:16 pm-10:15 pm
1 stop7h 59m
Chicago Midway
Wed 8/5
6:05 am-6:42 pm
2 stops14h 37m
$602
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 7/3
12:30 pm-10:17 pm
1 stop7h 47m
Chicago Midway
Fri 7/24
6:00 am-3:37 pm
2 stops11h 37m
$620
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 10/8
12:15 pm-12:45 am
2 stops10h 30m
Chicago Midway
Tue 10/13
6:00 am-1:40 pm
2 stops9h 40m
$638
Quickest round-trip
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 6/26
10:40 am-12:35 am
2 stops11h 55m
Chicago Midway
Mon 6/29
5:20 am-9:45 am
1 stop6h 25m
$659
Cheapest one-way
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 6/11
6:50 am-7:34 pm
1 stop10h 44m
$288
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Wed 8/12
6:04 am-10:36 pm
2 stops14h 32m
$317
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 6/11
4:49 pm-7:04 pm
2 stops24h 15m
$321
Showing 1-10 of 16 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
Hammond
Porter
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.
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Other flights from San José del Cabo
Popular flights