$308+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Aug 9 — Aug 161
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 July 10, 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 July 10, 2026.
This Southwest deal was found by Cheapflights users on 7/9. 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 8/2711:40 am
SJD
- MDW
2 stops10h 05m
Southwest
Mon 8/315:25 am
MDW
- SJD
1 stop9h 25m
Southwest
Deal found 7/9![Southwest logo]()
$508
This Delta deal was found by Cheapflights users on 7/9. 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 9/109:14 am
SJD
- MDW
2 stops11h 31m
Delta
Tue 9/156:05 am
MDW
- SJD
1 stop7h 02m
Delta
Deal found 7/9![Delta logo]()
$590
This Volaris deal was found by Cheapflights users on 7/5. 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 7/5![Volaris logo]()
$591
This Mytrip deal was found by Cheapflights users on 7/9. 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.
Wed 7/297:37 pm
SJD
- MDW
2 stops21h 57m
Volaris
Sun 8/28:23 pm
MDW
- SJD
2 stops18h 04m
Volaris
Deal found 7/9![Volaris logo]()
$618
This Delta deal was found by Cheapflights users on 7/8. 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 11/2411:57 am
SJD
- MDW
2 stops19h 48m
Delta
Fri 11/2712:30 pm
MDW
- SJD
2 stops27h 05m
Delta
Deal found 7/8![Delta logo]()
$620
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 7/306:50 am
SJD
- MDW
1 stop10h 44m
Multiple Airlines
Mon 8/38:23 pm
MDW
- SJD
1 stop20h 28m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$640
This Delta deal was found by Cheapflights users on 7/8. 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 11/2411:57 am
SJD
- MDW
2 stops19h 48m
Delta
Tue 12/16:00 am
MDW
- SJD
1 stop7h 25m
Delta
Deal found 7/8![Delta logo]()
$646
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/308:50 am
SJD
- MDW
1 stop8h 44m
Multiple Airlines
Sun 8/28:23 pm
MDW
- SJD
1 stop22h 27m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$649
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 July 10, 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 July 10, 2026.
This Southwest deal was found by Cheapflights users on 7/9. 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 8/2711:40 am
SJD
- MDW
2 stops10h 05m
Southwest
Mon 8/315:30 am
MDW
- SJD
2 stops9h 20m
Southwest
Deal found 7/9![Southwest logo]()
$513
This Delta deal was found by Cheapflights users on 7/9. 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 9/109:14 am
SJD
- MDW
2 stops11h 31m
Delta
Tue 9/156:05 am
MDW
- SJD
1 stop7h 02m
Delta
Deal found 7/9![Delta logo]()
$590
This Volaris deal was found by Cheapflights users on 7/6. 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 7/6![Volaris logo]()
$591
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/308:50 am
SJD
- MDW
1 stop8h 44m
Multiple Airlines
Sun 8/28:23 pm
MDW
- SJD
1 stop22h 27m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$649
This Southwest deal was found by Cheapflights users on 7/9. 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 7/3011:15 am
SJD
- MDW
2 stops11h 00m
Southwest
Mon 8/35:45 am
MDW
- SJD
2 stops9h 55m
Southwest
Deal found 7/9![Southwest logo]()
$664
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 7/258:50 am
SJD
- MDW
1 stop8h 44m
Multiple Airlines
Wed 7/298:23 pm
MDW
- SJD
1 stop11h 57m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 7/5. 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 12/234:30 pm
SJD
- MDW
1 stop12h 15m
Southwest
Thu 1/75:20 am
MDW
- SJD
1 stop7h 20m
Southwest
Deal found 7/5![Southwest logo]()
$686
Last-minute flights from San José del Cabo to MidwayDiscover last-minute flight deals from San José del Cabo to Midway. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated July 10, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 7/9. 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.
Wed 7/297:37 pm
SJD
- MDW
2 stops21h 57m
Volaris
Sun 8/28:23 pm
MDW
- SJD
2 stops18h 04m
Volaris
Deal found 7/9![Volaris logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 7/306:50 am
SJD
- MDW
1 stop10h 44m
Multiple Airlines
Mon 8/38:23 pm
MDW
- SJD
1 stop20h 28m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$640
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/308:50 am
SJD
- MDW
1 stop8h 44m
Multiple Airlines
Sun 8/28:23 pm
MDW
- SJD
1 stop22h 27m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$649
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/308:50 am
SJD
- MDW
1 stop8h 44m
Volaris
Mon 8/38:23 pm
MDW
- SJD
1 stop17h 06m
Volaris
Deal found 7/6![Volaris logo]()
$653
This Volaris deal was found by Cheapflights users on 7/5. 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 7/5![Volaris logo]()
$591
This Southwest deal was found by Cheapflights users on 7/9. 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 8/2711:40 am
SJD
- MDW
2 stops10h 05m
Southwest
Mon 8/315:25 am
MDW
- SJD
1 stop9h 25m
Southwest
Deal found 7/9![Southwest logo]()
$508
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 July 10, 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 July 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 12/511:16 am
SJD
- MDW
1 stop28h 23m
Volaris
Deal found 7/6![Volaris logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 8/237:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 7/7![Volaris logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 12/67:49 pm
SJD
- MDW
3 stops44h 16m
Volaris
Deal found 7/8![Volaris logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/227:37 pm
SJD
- MDW
2 stops21h 27m
Volaris
Deal found 7/6![Volaris logo]()
$341
This Delta deal was found by Cheapflights users on 7/9. 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 9/412:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 7/9![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 7/6. 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 7/291:25 pm
SJD
- MDW
2 stops17h 48m
Delta
Deal found 7/6![Delta logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 7/217:47 pm
SJD
- MDW
2 stops18h 03m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 7/7. 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 7/301:15 pm
SJD
- MDW
1 stop14h 10m
Southwest
Deal found 7/7![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 7/6. 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 7/301:25 pm
SJD
- MDW
2 stops17h 12m
Delta
Deal found 7/6![Delta logo]()
$353
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 July 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $508 (Southwest) |
One-way from | $308 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $540 |
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 July 10, 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
Thu 8/27
11:40 am-11:45 pm
2 stops10h 05m
Chicago Midway
Mon 8/31
5:30 am-12:50 pm
2 stops9h 20m
$513
Quickest round-trip
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 9/10
9:14 am-10:45 pm
2 stops11h 31m
Chicago Midway
Tue 9/15
6:05 am-11:07 am
1 stop7h 02m
$590
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
$591
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 7/30
8:50 am-7:34 pm
1 stop8h 44m
Chicago Midway
Sun 8/2
8:23 pm-4:50 pm
1 stop22h 27m
$649
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 7/30
11:15 am-12:15 am
2 stops11h 00m
Chicago Midway
Mon 8/3
5:45 am-1:40 pm
2 stops9h 55m
$664
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Wed 12/23
4:30 pm-5:45 am
1 stop12h 15m
Chicago Midway
Thu 1/7
5:20 am-11:40 am
1 stop7h 20m
$686
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Sat 7/25
8:50 am-7:34 pm
1 stop8h 44m
Chicago Midway
Wed 7/29
8:23 pm-6:20 am
1 stop11h 57m
$695
Cheapest one-way
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Sun 12/6
11:16 am-4:39 pm
1 stop28h 23m
$336
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 9/4
2:24 pm-8:39 am
2 stops16h 15m
$346
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 7/30
1:15 pm-5:25 am
1 stop14h 10m
$352
Showing 1-10 of 17 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
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Lansing
Merrillville
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Porter
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