$252+ Cheap flights from San José del Cabo (SJD) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
Nov 10 — Nov 171
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 October 11, 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 October 11, 2026.
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:04 pm -
1 stop7h 50m
Sun 12/66:00 am -
1 stop7h 59m
Deal found 10/10![Delta logo]()
$572
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/111:50 am -
1 stop10h 20m
Sun 12/65:20 am -
2 stops9h 55m
Deal found 10/10![Southwest logo]()
$642
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Thu 10/1512:06 pm -
1 stop28h 58m
Mon 10/198:23 pm -
2 stops15h 46m
Deal found 10/8![Volaris logo]()
$652
This Delta deal was found by Cheapflights users on 10/7. 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 11/212:04 pm -
1 stop7h 50m
Sat 11/286:00 am -
1 stop9h 23m
Deal found 10/7![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 10/7. 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.
Sat 11/214:45 pm -
1 stop12h 00m
Sat 11/285:20 am -
2 stops11h 30m
Deal found 10/7![Southwest logo]()
$705
This Booking.com deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:18 pm -
3 stops17h 15m
Sun 12/69:37 pm -
3 stops19h 54m
Deal found 10/10![Multiple Airlines logo]()
$762
This Southwest deal was found by Cheapflights users on 10/6. 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.
Fri 10/92:15 pm -
1 stop8h 00m
Tue 10/136:05 am -
1 stop8h 00m
Deal found 10/6![Southwest logo]()
$805
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 October 11, 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 October 11, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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 1/143:05 pm -
2 stops16h 40m
Tue 1/196:00 am -
2 stops12h 41m
Deal found 10/9![Delta logo]()
$524
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/111:50 am -
1 stop10h 20m
Sun 12/65:20 am -
2 stops9h 55m
Deal found 10/10![Southwest logo]()
$642
This Trip.com deal was found by Cheapflights users on 10/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:04 pm -
1 stop7h 50m
Mon 12/75:12 pm -
1 stop20h 47m
Deal found 10/7![Multiple Airlines logo]()
$956
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:04 pm -
1 stop7h 50m
Sun 12/66:00 am -
1 stop7h 59m
Deal found 10/10![Delta logo]()
$572
This Southwest deal was found by Cheapflights users on 10/7. 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.
Sat 11/214:45 pm -
1 stop12h 00m
Sat 11/285:20 am -
2 stops11h 30m
Deal found 10/7![Southwest logo]()
$705
This Delta deal was found by Cheapflights users on 10/7. 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 11/212:04 pm -
1 stop7h 50m
Sat 11/286:00 am -
1 stop9h 23m
Deal found 10/7![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 10/8. 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.
Mon 3/112:00 pm -
2 stops10h 20m
Mon 3/1510:10 am -
Nonstop4h 45m
Deal found 10/8![Southwest logo]()
$722
Last-minute flights from San José del Cabo to MidwayDiscover last-minute flight deals from San José del Cabo to Midway. Data last updated October 11, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated October 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/6. 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.
Fri 10/92:15 pm -
1 stop8h 00m
Tue 10/136:05 am -
1 stop8h 00m
Deal found 10/6![Southwest logo]()
$805
This Mytrip deal was found by Cheapflights users on 10/8. 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.
Fri 10/94:10 pm -
3 stops23h 50m
Tue 10/136:44 pm -
3 stops26h 40m
Deal found 10/8![Multiple Airlines logo]()
$3,674
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Thu 10/1512:06 pm -
1 stop28h 58m
Mon 10/198:23 pm -
2 stops15h 46m
Deal found 10/8![Volaris logo]()
$652
This Trip.com deal was found by Cheapflights users on 10/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:04 pm -
1 stop7h 50m
Mon 12/75:12 pm -
1 stop20h 47m
Deal found 10/7![Multiple Airlines logo]()
$956
This Delta deal was found by Cheapflights users on 10/7. 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 11/212:04 pm -
1 stop7h 50m
Sat 11/286:00 am -
1 stop9h 23m
Deal found 10/7![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 10/7. 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.
Sat 11/214:45 pm -
1 stop12h 00m
Sat 11/285:20 am -
2 stops11h 30m
Deal found 10/7![Southwest logo]()
$705
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 October 11, 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 October 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 12/75:18 pm -
3 stops41h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Fri 12/47:26 am -
3 stops54h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Thu 11/59:31 pm -
2 stops25h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Tue 12/89:31 pm -
1 stop18h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Tue 11/104:40 pm -
3 stops48h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 12/39:31 pm -
1 stop18h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Thu 12/35:18 pm -
1 stop22h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Volaris logo]()
$266
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 October 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $522 (Southwest) |
One-way from | $252 (Kiwi.com) |
Popular in | October |
Cheapest in | December |
Average price | $856 |
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 October 11, 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 11/6
3:10 pm-5:40 am
1 stop13h 30m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$283
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 11/5
11:50 am-1:10 am
1 stop12h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$283
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 11/11
2:05 pm-12:15 am
1 stop9h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$331
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 11/4
1:25 pm-10:33 pm
1 stop8h 08m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$332
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Tue 11/3
3:40 pm-9:32 am
2 stops16h 52m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$332
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 4/9
11:35 am-8:45 am
2 stops19h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$336
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 4/8
11:35 am-8:45 am
2 stops19h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$336
Quickest round-trip
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Wed 11/11
2:04 pm-10:54 pm
1 stop7h 50m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$339
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Fri 1/8
4:00 pm-12:33 pm
2 stops19h 33m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$344
San José del CaboChicago
SJD San José del Cabo Los Cabos - MDW Chicago Midway
SJDMDW
San José del Cabo Los Cabos
Thu 1/14
3:05 pm-8:45 am
2 stops16h 40m
Chicago Midway
Tue 1/19
6:00 am-5:41 pm
2 stops12h 41m
$524
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
Valparaiso
Hammond
Saint Joseph
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