$219+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJD — MDW
May 4 — May 111
Round-trip
1 adult, Economy
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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 April 4, 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 April 4, 2026.
This Southwest deal was found by Cheapflights users on 4/2. 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 7/201:05 pm
SJD
- MDW
1 stop7h 55m
Southwest
Mon 7/275:05 am
MDW
- SJD
1 stop7h 15m
Southwest
Deal found 4/2![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 3/31. 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 6/2010:35 am
SJD
- MDW
1 stop11h 05m
Southwest
Sun 6/285:00 am
MDW
- SJD
1 stop7h 40m
Southwest
Deal found 3/31![Southwest logo]()
$549
This Southwest deal was found by Cheapflights users on 3/31. 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 7/232:35 pm
SJD
- MDW
1 stop8h 00m
Southwest
Sat 8/15:25 am
MDW
- SJD
1 stop7h 55m
Southwest
Deal found 3/31![Southwest logo]()
$554
This Southwest deal was found by Cheapflights users on 3/30. 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 5/141:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Thu 5/215:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Deal found 3/30![Southwest logo]()
$643
This Delta deal was found by Cheapflights users on 4/1. 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 10/312:15 pm
SJD
- MDW
1 stop7h 31m
Delta
Sat 10/1010:35 am
MDW
- SJD
2 stops13h 53m
Delta
Deal found 4/1![Delta logo]()
$647
This Mytrip deal was found by Cheapflights users on 4/1. 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 10/312:02 pm
SJD
- MDW
3 stops29h 02m
Volaris
Sat 10/107:30 pm
MDW
- SJD
2 stops25h 27m
Volaris
Deal found 4/1![Volaris logo]()
$659
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/88:30 am
SJD
- MDW
1 stop8h 34m
Volaris
Wed 4/158:23 pm
MDW
- SJD
1 stop17h 09m
Volaris
Deal found 3/31![Volaris logo]()
$673
This Southwest deal was found by Cheapflights users on 4/1. 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 6/41:15 pm
SJD
- MDW
1 stop14h 10m
Southwest
Sun 6/75:25 am
MDW
- SJD
1 stop7h 55m
Southwest
Deal found 4/1![Southwest logo]()
$689
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 April 4, 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 April 4, 2026.
This Southwest deal was found by Cheapflights users on 4/2. 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 7/201:05 pm
SJD
- MDW
1 stop7h 55m
Southwest
Mon 7/275:05 am
MDW
- SJD
1 stop7h 15m
Southwest
Deal found 4/2![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 3/31. 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 7/2311:35 am
SJD
- MDW
1 stop10h 20m
Southwest
Sat 8/15:25 am
MDW
- SJD
2 stops9h 15m
Southwest
Deal found 3/31![Southwest logo]()
$591
This Southwest deal was found by Cheapflights users on 3/30. 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 5/141:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Thu 5/215:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Deal found 3/30![Southwest logo]()
$643
This Southwest deal was found by Cheapflights users on 4/1. 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 6/41:15 pm
SJD
- MDW
1 stop14h 10m
Southwest
Sun 6/75:25 am
MDW
- SJD
1 stop7h 55m
Southwest
Deal found 4/1![Southwest logo]()
$689
This Southwest deal was found by Cheapflights users on 4/1. 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 6/510:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Sun 6/77:00 am
MDW
- SJD
1 stop7h 25m
Southwest
Deal found 4/1![Southwest logo]()
$694
This Southwest deal was found by Cheapflights users on 3/31. 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 5/153:05 pm
SJD
- MDW
1 stop11h 55m
Southwest
Fri 5/225:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Deal found 3/31![Southwest logo]()
$833
This Southwest deal was found by Cheapflights users on 4/1. 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 5/173:05 pm
SJD
- MDW
1 stop12h 40m
Southwest
Sun 5/248:45 am
MDW
- SJD
1 stop6h 55m
Southwest
Deal found 4/1![Southwest logo]()
$878
Last-minute flights from San José del Cabo to MidwayDiscover last-minute flight deals from San José del Cabo to Midway. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from San José del Cabo to Midway. Data last updated April 4, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/88:30 am
SJD
- MDW
1 stop8h 34m
Volaris
Wed 4/158:23 pm
MDW
- SJD
1 stop17h 09m
Volaris
Deal found 3/31![Volaris logo]()
$673
This Delta deal was found by Cheapflights users on 3/31. 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 4/812:35 pm
SJD
- MDW
1 stop7h 56m
Delta
Wed 4/156:00 am
MDW
- SJD
1 stop7h 31m
Delta
Deal found 3/31![Delta logo]()
$699
This Southwest deal was found by Cheapflights users on 3/31. 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 4/82:20 pm
SJD
- MDW
2 stops13h 05m
Southwest
Wed 4/157:30 am
MDW
- SJD
1 stop7h 55m
Southwest
Deal found 3/31![Southwest logo]()
$774
This Southwest deal was found by Cheapflights users on 4/3. 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 4/1010:45 am
SJD
- MDW
1 stop9h 10m
Southwest
Fri 4/176:55 am
MDW
- SJD
1 stop7h 15m
Southwest
Deal found 4/3![Southwest logo]()
$784
This Mytrip deal was found by Cheapflights users on 4/3. 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 4/108:30 am
SJD
- MDW
1 stop8h 34m
Volaris
Fri 4/178:23 pm
MDW
- SJD
2 stops17h 02m
Volaris
Deal found 4/3![Volaris logo]()
$818
This Southwest deal was found by Cheapflights users on 3/30. 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 5/141:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Thu 5/215:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Deal found 3/30![Southwest logo]()
$643
This Southwest deal was found by Cheapflights users on 3/31. 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 5/153:05 pm
SJD
- MDW
1 stop11h 55m
Southwest
Fri 5/225:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Deal found 3/31![Southwest logo]()
$833
This Southwest deal was found by Cheapflights users on 4/1. 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 5/173:05 pm
SJD
- MDW
1 stop12h 40m
Southwest
Sun 5/248:45 am
MDW
- SJD
1 stop6h 55m
Southwest
Deal found 4/1![Southwest logo]()
$878
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 April 4, 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 April 4, 2026.
This Super.com deal was found by Cheapflights users on 3/30. 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.
Sat 4/1111:27 am
SJD
- MDW
1 stop9h 02m
Frontier
Deal found 3/30![Frontier logo]()
$219
This Volaris deal was found by Cheapflights users on 3/29. 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.
Sun 6/78:16 am
SJD
- MDW
1 stop8h 48m
Volaris
Deal found 3/29![Volaris logo]()
$227
This Delta deal was found by Cheapflights users on 3/30. 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 5/12:00 pm
SJD
- MDW
2 stops18h 14m
Delta
Deal found 3/30![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 4/1. 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 7/212:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Deal found 4/1![Delta logo]()
$247
This Booking.com deal was found by Cheapflights users on 4/1. 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.
Sun 6/218:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 4/1![Volaris logo]()
$250
This Southwest deal was found by Cheapflights users on 3/31. 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 6/303:15 pm
SJD
- MDW
1 stop11h 55m
Southwest
Deal found 3/31![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 4/2. 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 6/41:09 pm
SJD
- MDW
2 stops17h 34m
Delta
Deal found 4/2![Delta logo]()
$254
This Delta deal was found by Cheapflights users on 4/2. 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 4/2912:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 4/2![Delta logo]()
$255
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 April 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $547 (Southwest) |
One-way from | $219 (Super.com) |
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 April 4, 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
Quickest round-trip
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Mon 7/20
1:05 pm-11:00 pm
1 stop7h 55m
Chicago Midway
Mon 7/27
5:05 am-10:20 am
1 stop7h 15m
$547
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 7/23
11:35 am-11:55 pm
1 stop10h 20m
Chicago Midway
Sat 8/1
5:25 am-12:40 pm
2 stops9h 15m
$591
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 5/14
1:55 pm-4:35 am
1 stop12h 40m
Chicago Midway
Thu 5/21
5:30 am-12:10 pm
2 stops8h 40m
$643
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 6/4
1:15 pm-5:25 am
1 stop14h 10m
Chicago Midway
Sun 6/7
5:25 am-11:20 am
1 stop7h 55m
$689
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 6/5
10:40 am-12:35 am
2 stops11h 55m
Chicago Midway
Sun 6/7
7:00 am-12:25 pm
1 stop7h 25m
$694
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 5/15
3:05 pm-5:00 am
1 stop11h 55m
Chicago Midway
Fri 5/22
5:30 am-12:10 pm
2 stops8h 40m
$833
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Sun 5/17
3:05 pm-5:45 am
1 stop12h 40m
Chicago Midway
Sun 5/24
8:45 am-1:40 pm
1 stop6h 55m
$878
Cheapest one-way
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Fri 5/29
1:35 pm-8:42 am
2 stops17h 07m
$241
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Tue 6/2
6:00 am-9:09 pm
2 stops13h 09m
$248
Quickest one-way
San José del CaboChicago
SJD - MDW
SJDMDW
San José del Cabo Los Cabos
Thu 7/2
12:30 pm-10:17 pm
1 stop7h 47m
$260
Showing 1-10 of 15 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.
Cheapflights Insights
Everything you need to know about your flight from San José del Cabo to Chicago Midway Airport
Related info for your journey
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