$133+ Cheap flights from Midway (MDW) to San José del Cabo (SJD)
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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Mar 11 — Mar 181
1 adult, Economy
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Cheapest flights from Midway to San José del CaboExplore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
Explore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJD
1 stop8h 40m
Southwest
Fri 3/61:35 pm
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 2/8![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 3/99:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Mon 3/1611:55 am
SJD
- MDW
Nonstop4h 00m
Southwest
Deal found 2/9![Southwest logo]()
$485
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- SJD
1 stop9h 09m
Delta
Fri 3/66:05 am
SJD
- MDW
2 stops15h 26m
Delta
Deal found 2/5![Delta logo]()
$486
This Expedia deal was found by Cheapflights users on 2/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
MDW
- SJD
1 stop9h 09m
Multiple Airlines
Sat 3/712:31 pm
SJD
- MDW
1 stop8h 53m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/36:00 am
MDW
- SJD
1 stop9h 09m
Delta
Fri 3/66:05 am
SJD
- MDW
2 stops15h 26m
Delta
Deal found 2/9![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 2/6. 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.
Sat 2/216:00 am
MDW
- SJD
2 stops12h 37m
Delta
Sat 2/281:45 pm
SJD
- MDW
1 stop7h 46m
Delta
Deal found 2/6![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 2/9. 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 3/59:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Tue 3/1011:35 am
SJD
- MDW
1 stop10h 35m
Southwest
Deal found 2/9![Southwest logo]()
$495
This CheapOair deal was found by Cheapflights users on 2/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
MDW
- SJD
1 stop8h 23m
Frontier
Sat 2/212:38 pm
SJD
- MDW
1 stop28h 21m
Frontier
Deal found 2/8![Frontier logo]()
$497
This Delta deal was found by Cheapflights users on 2/6. 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.
Tue 5/2610:46 am
MDW
- SJD
2 stops13h 39m
Delta
Tue 6/26:00 am
SJD
- MDW
2 stops13h 09m
Delta
Deal found 2/6![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 2/8. 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.
Sat 5/26:00 am
MDW
- SJD
1 stop9h 04m
Delta
Sat 5/96:00 am
SJD
- MDW
2 stops13h 09m
Delta
Deal found 2/8![Delta logo]()
$504
Best flights from Midway to San José del CaboDiscover carefully curated flight deals from Midway to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
Discover carefully curated flight deals from Midway to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 9, 2026.
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- SJD
1 stop9h 09m
Delta
Fri 3/66:05 am
SJD
- MDW
2 stops15h 26m
Delta
Deal found 2/5![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/75:55 am
MDW
- SJD
1 stop9h 20m
Southwest
Wed 3/1111:35 am
SJD
- MDW
1 stop10h 35m
Southwest
Deal found 2/8![Southwest logo]()
$499
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:20 pm
MDW
- SJD
1 stop16h 24m
Delta
Fri 4/101:32 pm
SJD
- MDW
1 stop17h 18m
Delta
Deal found 2/7![Delta logo]()
$503
This Southwest deal was found by Cheapflights users on 2/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:25 am
MDW
- SJD
1 stop6h 50m
Southwest
Mon 3/231:55 pm
SJD
- MDW
1 stop8h 10m
Southwest
Deal found 2/6![Southwest logo]()
$503
This Delta deal was found by Cheapflights users on 2/6. 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.
Sat 5/210:43 am
MDW
- SJD
2 stops13h 42m
Delta
Sat 5/911:36 am
SJD
- MDW
1 stop7h 33m
Delta
Deal found 2/6![Delta logo]()
$504
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 3/95:40 am
MDW
- SJD
2 stops10h 45m
Southwest
Mon 3/163:20 pm
SJD
- MDW
1 stop12h 25m
Southwest
Deal found 2/9![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 2/7. 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.
Mon 4/206:55 am
MDW
- SJD
1 stop8h 30m
Southwest
Sat 4/2511:35 am
SJD
- MDW
2 stops9h 00m
Southwest
Deal found 2/7![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:43 am
MDW
- SJD
2 stops13h 47m
Delta
Sat 4/256:00 am
SJD
- MDW
2 stops14h 28m
Delta
Deal found 2/7![Delta logo]()
$518
This Southwest deal was found by Cheapflights users on 2/7. 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.
Sun 3/85:55 am
MDW
- SJD
1 stop8h 55m
Southwest
Sun 3/151:20 pm
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 2/7![Southwest logo]()
$518
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- SJD
1 stop7h 31m
Delta
Sat 5/1611:36 am
SJD
- MDW
1 stop7h 33m
Delta
Deal found 2/5![Delta logo]()
$526
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:40 pm
MDW
- SJD
2 stops15h 00m
Delta
Tue 2/241:45 pm
SJD
- MDW
1 stop7h 48m
Delta
Deal found 2/7![Delta logo]()
$534
Last-minute flights from Midway to San José del CaboDiscover last-minute flight deals from Midway to San José del Cabo. Data last updated February 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to San José del Cabo. Data last updated February 9, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
MDW
- SJD
1 stop8h 23m
Frontier
Sat 2/212:38 pm
SJD
- MDW
1 stop28h 21m
Frontier
Deal found 2/8![Frontier logo]()
$497
This Delta deal was found by Cheapflights users on 2/6. 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.
Sat 2/216:00 am
MDW
- SJD
1 stop7h 40m
Delta
Sat 2/281:45 pm
SJD
- MDW
1 stop7h 46m
Delta
Deal found 2/6![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJD
1 stop8h 40m
Southwest
Fri 3/61:35 pm
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 2/8![Southwest logo]()
$484
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
MDW
- SJD
1 stop9h 09m
Delta
Fri 3/66:05 am
SJD
- MDW
2 stops15h 26m
Delta
Deal found 2/5![Delta logo]()
$486
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/36:00 am
MDW
- SJD
1 stop9h 09m
Delta
Fri 3/66:05 am
SJD
- MDW
2 stops15h 26m
Delta
Deal found 2/9![Delta logo]()
$493
This Expedia deal was found by Cheapflights users on 2/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
MDW
- SJD
1 stop9h 09m
Multiple Airlines
Sat 3/712:31 pm
SJD
- MDW
1 stop8h 53m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 2/9. 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 3/59:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Tue 3/1011:35 am
SJD
- MDW
1 stop10h 35m
Southwest
Deal found 2/9![Southwest logo]()
$495
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 3/75:55 am
MDW
- SJD
1 stop9h 20m
Southwest
Wed 3/111:50 pm
SJD
- MDW
2 stops13h 30m
Southwest
Deal found 2/9![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 3/99:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Mon 3/1611:55 am
SJD
- MDW
Nonstop4h 00m
Southwest
Deal found 2/9![Southwest logo]()
$485
This Southwest deal was found by Cheapflights users on 2/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:25 am
MDW
- SJD
1 stop6h 50m
Southwest
Mon 3/231:55 pm
SJD
- MDW
1 stop8h 10m
Southwest
Deal found 2/6![Southwest logo]()
$503
One-way flights from Midway to San José del CaboSearch for one-way flight options from Midway to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
Search for one-way flight options from Midway to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated February 9, 2026.
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:53 pm
MDW
- SJD
1 stop18h 22m
Frontier
Deal found 2/6![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Mon 3/23:29 pm
MDW
- SJD
3 stops48h 51m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sat 2/289:15 am
MDW
- SJD
2 stops33h 35m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 5/46:15 am
MDW
- SJD
3 stops29h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 3/62:41 pm
MDW
- SJD
3 stops52h 09m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$173
This Mytrip deal was found by Cheapflights users on 2/9. 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.
Mon 3/26:54 pm
MDW
- SJD
2 stops16h 42m
Volaris
Deal found 2/9![Volaris logo]()
$179
This Delta deal was found by Cheapflights users on 2/9. 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.
Mon 2/236:00 am
MDW
- SJD
1 stop7h 40m
Delta
Deal found 2/9![Delta logo]()
$180
This Priceline deal was found by Cheapflights users on 2/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/102:56 pm
MDW
- SJD
1 stop21h 16m
Frontier
Deal found 2/9![Frontier logo]()
$181
This Mytrip deal was found by Cheapflights users on 2/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:54 pm
MDW
- SJD
2 stops16h 42m
Volaris
Deal found 2/8![Volaris logo]()
$183
Find flight deals from Midway to San José del Cabo
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José del Cabo (SJD). 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 February 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $484 (Southwest) |
One-way from | $133 (Trip.com) |
Popular in | December |
Cheapest in | October |
Average price | $1,112 |
Good round-trip deal | $612 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to San José del Cabo 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 February 9, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San José del Cabo that are best for you.
Fly from
Midway
Fly to
San José del Cabo
Route
Depart
Return
Price
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 3/1
6:00 am-2:09 pm
1 stop9h 09m
San José del Cabo Los Cabos
Fri 3/6
6:05 am-10:31 pm
2 stops15h 26m
$486
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 3/7
5:55 am-2:15 pm
1 stop9h 20m
San José del Cabo Los Cabos
Wed 3/11
11:35 am-12:10 am
1 stop10h 35m
$499
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 4/4
7:20 pm-9:44 am
1 stop16h 24m
San José del Cabo Los Cabos
Fri 4/10
1:32 pm-8:50 am
1 stop17h 18m
$503
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 3/18
6:25 am-11:15 am
1 stop6h 50m
San José del Cabo Los Cabos
Mon 3/23
1:55 pm-12:05 am
1 stop8h 10m
$503
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 5/2
10:43 am-10:25 pm
2 stops13h 42m
San José del Cabo Los Cabos
Sat 5/9
11:36 am-9:09 pm
1 stop7h 33m
$504
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 3/9
5:40 am-2:25 pm
2 stops10h 45m
San José del Cabo Los Cabos
Mon 3/16
3:20 pm-5:45 am
1 stop12h 25m
$504
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 4/20
6:55 am-1:25 pm
1 stop8h 30m
San José del Cabo Los Cabos
Sat 4/25
11:35 am-10:35 pm
2 stops9h 00m
$504
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 4/20
10:43 am-10:30 pm
2 stops13h 47m
San José del Cabo Los Cabos
Sat 4/25
6:00 am-10:28 pm
2 stops14h 28m
$518
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 3/8
5:55 am-12:50 pm
1 stop8h 55m
San José del Cabo Los Cabos
Sun 3/15
1:20 pm-7:15 pm
Nonstop3h 55m
$518
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 5/2
6:00 am-11:31 am
1 stop7h 31m
San José del Cabo Los Cabos
Sat 5/16
11:36 am-9:09 pm
1 stop7h 33m
$526
Showing 1-10 of 20 results
Compare providers for flights from Midway to San José del Cabo
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 Midway to San José del Cabo in February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-San José del Cabo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José del Cabo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José del Cabo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-San José del Cabo 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 Chicago Midway Airport-San José del Cabo 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 Midway to San José del Cabo
Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Midway with our price prediction graph.
MDW-SJD
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.
Reviews of airlines servicing San José del Cabo
Get insights into the airlines that provide service to San José del Cabo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José del Cabo. Reviews last updated February 9, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to San José del Cabo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Midway and San José del Cabo flights
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Top airline flying from Midway to San José del Cabo
Discover the top airline that operate flights from Midway to San José del Cabo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$485 | Average$675 | FlexibilityNo cancel fee | On-time63% |