$153+ Cheap flights from Midway (MDW) to Cabo San Lucas, Mexico
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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jun 18 — Jun 251
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Cabo San Lucas 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 Midway to Cabo San LucasExplore the most affordable flight options available from Midway to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
Explore the most affordable flight options available from Midway to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
This Delta deal was found by Cheapflights users on 5/14. 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 8/96:05 am
MDW
- SJD
2 stops18h 25m
Delta
Thu 8/136:04 am
SJD
- MDW
2 stops14h 32m
Delta
Deal found 5/14![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 5/14. 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 8/87:25 pm
MDW
- SJD
2 stops20h 14m
Delta
Thu 8/1312:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/14![Delta logo]()
$534
This Delta deal was found by Cheapflights users on 5/14. 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 8/96:05 am
MDW
- SJD
1 stop7h 02m
Delta
Fri 8/1412:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/14![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 5/14. 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 8/147:25 am
MDW
- SJD
1 stop7h 25m
Southwest
Tue 8/1811:40 am
SJD
- MDW
1 stop9h 30m
Southwest
Deal found 5/14![Southwest logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 5/16. 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.
Wed 8/268:23 pm
MDW
- SJD
1 stop18h 02m
Multiple Airlines
Sat 8/291:10 pm
SJD
- MDW
1 stop27h 54m
Multiple Airlines
Deal found 5/16![Multiple Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 5/14. 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 8/66:05 am
MDW
- SJD
1 stop7h 02m
Delta
Wed 8/1212:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/14![Delta logo]()
$574
This Gotogate deal was found by Cheapflights users on 5/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Thu 7/238:50 am
SJD
- MDW
1 stop8h 44m
Volaris
Deal found 5/15![Volaris logo]()
$583
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.
Wed 9/96:00 am
MDW
- SJD
1 stop7h 22m
Delta
Wed 9/1612:15 pm
SJD
- MDW
1 stop7h 31m
Delta
Deal found 5/19![Delta logo]()
$585
This Southwest deal was found by Cheapflights users on 5/14. 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 7/58:30 am
MDW
- SJD
1 stop6h 55m
Southwest
Fri 7/109:45 am
SJD
- MDW
1 stop9h 30m
Southwest
Deal found 5/14![Southwest logo]()
$586
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.
Fri 10/28:23 pm
MDW
- SJD
1 stop20h 28m
Volaris
Sun 10/1111:29 am
SJD
- MDW
2 stops29h 35m
Volaris
Deal found 5/18![Volaris logo]()
$589
This Southwest deal was found by Cheapflights users on 5/16. 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 10/136:10 am
MDW
- SJD
1 stop9h 10m
Southwest
Tue 10/2712:15 pm
SJD
- MDW
2 stops9h 35m
Southwest
Deal found 5/16![Southwest logo]()
$590
Best flights from Midway to Cabo San LucasDiscover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
Discover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am
MDW
- SJD
1 stop7h 25m
Delta
Thu 11/1911:57 am
SJD
- MDW
1 stop8h 48m
Delta
Deal found 5/17![Delta logo]()
$619
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.
Sun 6/145:25 am
MDW
- SJD
1 stop7h 35m
Southwest
Wed 6/1710:40 am
SJD
- MDW
1 stop11h 10m
Southwest
Deal found 5/19![Southwest logo]()
$653
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- SJD
1 stop7h 11m
Delta
Tue 8/42:44 pm
SJD
- MDW
2 stops15h 56m
Delta
Deal found 5/17![Delta logo]()
$658
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.
Wed 10/286:00 am
MDW
- SJD
2 stops9h 40m
Southwest
Sun 11/112:35 pm
SJD
- MDW
1 stop10h 10m
Southwest
Deal found 5/18![Southwest logo]()
$671
This Delta deal was found by Cheapflights users on 5/15. 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 7/186:00 am
MDW
- SJD
2 stops12h 46m
Delta
Thu 7/2312:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 5/15![Delta logo]()
$678
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 7/205:00 am
MDW
- SJD
2 stops10h 25m
Southwest
Sat 7/2511:35 am
SJD
- MDW
2 stops10h 05m
Southwest
Deal found 5/18![Southwest logo]()
$683
This Delta deal was found by Cheapflights users on 5/16. 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 8/96:05 am
MDW
- SJD
2 stops11h 13m
Delta
Sun 8/162:44 pm
SJD
- MDW
2 stops15h 56m
Delta
Deal found 5/16![Delta logo]()
$683
This Southwest deal was found by Cheapflights users on 5/14. 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 6/410:10 am
MDW
- SJD
1 stop6h 15m
Southwest
Mon 6/811:15 am
SJD
- MDW
1 stop8h 00m
Southwest
Deal found 5/14![Southwest logo]()
$693
This Southwest deal was found by Cheapflights users on 5/14. 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 6/86:40 am
MDW
- SJD
2 stops9h 45m
Southwest
Wed 6/1011:35 am
SJD
- MDW
2 stops10h 30m
Southwest
Deal found 5/14![Southwest logo]()
$698
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
MDW
- SJD
1 stop7h 10m
Delta
Sat 9/196:04 am
SJD
- MDW
2 stops13h 42m
Delta
Deal found 5/17![Delta logo]()
$703
This Delta deal was found by Cheapflights users on 5/16. 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 10/1710:35 am
MDW
- SJD
2 stops13h 53m
Delta
Sat 10/246:04 am
SJD
- MDW
2 stops13h 41m
Delta
Deal found 5/16![Delta logo]()
$703
Last-minute flights from Midway to Cabo San LucasDiscover last-minute flight deals from Midway to Cabo San Lucas. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cabo San Lucas. Data last updated May 19, 2026 and is based on user searches.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:48 pm
MDW
- SJD
2 stops16h 05m
Volaris
Wed 5/277:37 pm
SJD
- MDW
2 stops21h 43m
Volaris
Deal found 5/18![Volaris logo]()
$644
This Mytrip deal was found by Cheapflights users on 5/14. 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 5/238:48 pm
MDW
- SJD
3 stops24h 07m
Volaris
Tue 5/267:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 5/14![Volaris logo]()
$659
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.
Tue 6/23:07 pm
MDW
- SJD
2 stops18h 13m
Multiple Airlines
Sun 6/76:50 am
SJD
- MDW
1 stop10h 14m
Multiple Airlines
Deal found 5/19![Multiple Airlines logo]()
$631
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:49 pm
MDW
- SJD
1 stop11h 31m
Multiple Airlines
Sun 6/146:50 am
SJD
- MDW
1 stop10h 14m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$640
This Southwest deal was found by Cheapflights users on 5/14. 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 6/85:05 am
MDW
- SJD
1 stop7h 15m
Southwest
Wed 6/101:15 pm
SJD
- MDW
1 stop8h 35m
Southwest
Deal found 5/14![Southwest logo]()
$643
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.
Sun 6/145:25 am
MDW
- SJD
1 stop7h 35m
Southwest
Wed 6/1711:35 am
SJD
- MDW
2 stops10h 30m
Southwest
Deal found 5/19![Southwest logo]()
$658
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.
Wed 6/178:23 pm
MDW
- SJD
1 stop11h 57m
Multiple Airlines
Sun 6/216:50 am
SJD
- MDW
1 stop10h 14m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$649
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.
Sat 6/208:49 pm
MDW
- SJD
1 stop11h 31m
Multiple Airlines
Sat 6/271:10 pm
SJD
- MDW
1 stop27h 54m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$593
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:49 pm
MDW
- SJD
3 stops24h 08m
Volaris
Sat 6/277:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 5/18![Volaris logo]()
$655
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.
Sun 6/286:00 am
MDW
- SJD
1 stop7h 25m
Delta
Fri 7/312:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Deal found 5/18![Delta logo]()
$653
One-way flights from Midway to Cabo San LucasSearch for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
Search for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This Super.com deal was found by Cheapflights users on 5/15. 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.
Tue 7/218:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/15![Volaris logo]()
$153
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.
Thu 7/168:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/17![Volaris logo]()
$184
This Trip.com deal was found by Cheapflights users on 5/14. 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.
Tue 7/288:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/14![Volaris logo]()
$215
This Trip.com deal was found by Cheapflights users on 5/14. 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.
Sat 8/18:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/14![Volaris logo]()
$217
This Mytrip deal was found by Cheapflights users on 5/15. 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 7/208:23 pm
MDW
- SJD
2 stops16h 30m
Volaris
Deal found 5/15![Volaris logo]()
$258
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 7/93:22 pm
MDW
- SJD
3 stops27h 28m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$261
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:49 pm
MDW
- SJD
2 stops16h 04m
Volaris
Deal found 5/19![Volaris logo]()
$270
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:35 am
MDW
- SJD
2 stops24h 58m
Aeromexico
Deal found 5/17![Aeromexico logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 5/15. 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 6/118:49 pm
MDW
- SJD
1 stop17h 41m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 7/2812:11 pm
MDW
- SJD
3 stops55h 49m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$279
Find flight deals from Midway to Cabo San Lucas
Keep the following information in mind while searching for Midway to Cabo San Lucas flight deals. Data was last updated May 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $529 (Delta) |
One-way from | $153 (Super.com) |
Popular in | December |
Cheapest in | October |
Average price | $736 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Cabo San Lucas 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 19, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cabo San Lucas that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 11/9
6:00 am-12:25 pm
1 stop7h 25m
San José del Cabo Los Cabos
Thu 11/19
11:57 am-9:45 pm
1 stop8h 48m
$619
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 6/14
5:25 am-11:00 am
1 stop7h 35m
San José del Cabo Los Cabos
Wed 6/17
10:40 am-11:50 pm
1 stop11h 10m
$653
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 7/29
6:00 am-11:11 am
1 stop7h 11m
San José del Cabo Los Cabos
Tue 8/4
2:44 pm-8:40 am
2 stops15h 56m
$658
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 10/28
6:00 am-1:40 pm
2 stops9h 40m
San José del Cabo Los Cabos
Sun 11/1
12:35 pm-11:45 pm
1 stop10h 10m
$671
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 7/18
6:00 am-4:46 pm
2 stops12h 46m
San José del Cabo Los Cabos
Thu 7/23
12:16 pm-10:15 pm
1 stop7h 59m
$678
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 7/20
5:00 am-1:25 pm
2 stops10h 25m
San José del Cabo Los Cabos
Sat 7/25
11:35 am-11:40 pm
2 stops10h 05m
$683
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 8/9
6:05 am-3:18 pm
2 stops11h 13m
San José del Cabo Los Cabos
Sun 8/16
2:44 pm-8:40 am
2 stops15h 56m
$683
Quickest round-trip
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Thu 6/4
10:10 am-2:25 pm
1 stop6h 15m
San José del Cabo Los Cabos
Mon 6/8
11:15 am-9:15 pm
1 stop8h 00m
$693
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 6/8
6:40 am-2:25 pm
2 stops9h 45m
San José del Cabo Los Cabos
Wed 6/10
11:35 am-12:05 am
2 stops10h 30m
$698
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 9/12
6:00 am-11:10 am
1 stop7h 10m
San José del Cabo Los Cabos
Sat 9/19
6:04 am-9:46 pm
2 stops13h 42m
$703
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Midway to Cabo San Lucas
Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Midway with our price prediction graph.
MDW-SJD
Estimated round-trip price
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Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Cabo San Lucas
MDW-C4B
MDW-SJD
How much does it cost to fly round-trip from Chicago Midway Airport to Cabo San Lucas?
Reviews of airlines servicing Cabo San Lucas
Get insights into the airlines that provide service to Cabo San Lucas. 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 Cabo San Lucas. Reviews last updated May 19, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cabo San Lucas, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Cabo San Lucas. 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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Alternative routes for Midway to Cabo San Lucas
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Complete your trip
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Midway and Cabo San Lucas flights
Browse other Midway and Cabo San Lucas flight options. Last updated on May 19, 2026.
Other flights from Midway
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Midway to Cabo San Lucas flights
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Top airline flying from Midway to Cabo San Lucas
Discover the top airline that operate flights from Midway to Cabo San Lucas. 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 May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |