$98+ Cheap flights from Chicago (CHI) 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Apr 19 — Apr 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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
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.Cheapflights Tip: The best prices from Chicago to Cabo San Lucas are usually found in September or August, booked 41 days in advance, depart on a Tuesday or Friday and return on a Thursday
Cheap flight deals from Chicago to Cabo San Lucas
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Best
Last-minute
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Cheapest flights from Chicago to Cabo San LucasExplore the most affordable flight options available from Chicago to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 20, 2026.
Explore the most affordable flight options available from Chicago to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/171:49 pm
ORD
- SJD
2 stops28h 15m
Multiple Airlines
Fri 4/242:15 pm
SJD
- ORD
2 stops22h 34m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$420
This Volaris deal was found by Cheapflights users on 3/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 4/147:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/17![Volaris logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/118:25 pm
ORD
- SJD
1 stop11h 50m
Multiple Airlines
Sat 4/181:05 pm
SJD
- ORD
1 stop9h 50m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Sun 5/32:35 am
ORD
- SJD
1 stop11h 50m
Multiple Airlines
Sun 5/102:15 pm
SJD
- ORD
2 stops22h 20m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:00 am
ORD
- SJD
1 stop9h 36m
Alaska Airlines
Fri 5/222:42 pm
SJD
- ORD
1 stop26h 08m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
- SJD
1 stop17h 45m
Alaska Airlines
Wed 5/63:47 pm
SJD
- ORD
1 stop25h 16m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 3/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:48 pm
ORD
- SJD
1 stop19h 49m
Alaska Airlines
Sat 5/910:41 am
SJD
- ORD
1 stop24h 32m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 5/61:49 pm
ORD
- SJD
1 stop18h 26m
Multiple Airlines
Sun 5/1010:05 am
SJD
- ORD
3 stops12h 40m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$427
This Volaris deal was found by Cheapflights users on 3/20. 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.
Tue 5/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 5/2412:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/20![Volaris logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Sat 5/238:25 pm
ORD
- SJD
1 stop11h 50m
Viva
Sat 5/301:05 pm
SJD
- ORD
1 stop8h 40m
Viva
Deal found 3/16![Viva logo]()
$429
This Volaris deal was found by Cheapflights users on 3/17. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/17![Volaris logo]()
$431
This Delta deal was found by Cheapflights users on 3/16. 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 5/36:00 am
MDW
- SJD
1 stop7h 31m
Delta
Wed 5/612:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/16![Delta logo]()
$454
Best flights from Chicago to Cabo San LucasDiscover carefully curated flight deals from Chicago to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 20, 2026.
Discover carefully curated flight deals from Chicago to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:59 pm
ORD
- SJD
1 stop17h 35m
Alaska Airlines
Fri 4/172:30 pm
SJD
- ORD
2 stops26h 32m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$436
This Volaris deal was found by Cheapflights users on 3/18. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 4/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/18![Volaris logo]()
$457
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Wed 4/1511:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 3/16![United Airlines logo]()
$461
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 4/157:10 am
ORD
- SJD
2 stops12h 39m
Delta
Wed 4/226:01 am
SJD
- ORD
2 stops12h 15m
Delta
Deal found 3/15![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:25 am
MDW
- SJD
1 stop6h 45m
Southwest
Sat 5/163:10 pm
SJD
- MDW
1 stop12h 30m
Southwest
Deal found 3/17![Southwest logo]()
$520
This Volaris deal was found by Cheapflights users on 3/19. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 4/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/19![Volaris logo]()
$458
This Delta deal was found by Cheapflights users on 3/17. 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.
Fri 5/156:24 am
ORD
- SJD
2 stops13h 24m
Delta
Wed 5/2010:24 am
SJD
- ORD
1 stop11h 46m
Delta
Deal found 3/17![Delta logo]()
$489
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Mon 4/1311:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 3/17![United Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 3/18. 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 4/135:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Fri 4/171:25 pm
SJD
- MDW
1 stop6h 30m
Southwest
Deal found 3/18![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 3/19. 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.
Tue 5/55:15 am
ORD
- SJD
2 stops14h 33m
Delta
Sun 5/1010:24 am
SJD
- ORD
1 stop11h 46m
Delta
Deal found 3/19![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 3/19. 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.
Mon 5/1110:24 am
ORD
- SJD
2 stops14h 04m
Delta
Sun 5/172:36 pm
SJD
- ORD
1 stop7h 34m
Delta
Deal found 3/19![Delta logo]()
$489
This Delta deal was found by Cheapflights users on 3/19. 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 5/69:50 am
ORD
- SJD
2 stops14h 28m
Delta
Sun 5/1010:24 am
SJD
- ORD
1 stop11h 46m
Delta
Deal found 3/19![Delta logo]()
$489
This Southwest deal was found by Cheapflights users on 3/19. 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 6/145:15 am
MDW
- SJD
1 stop9h 55m
Southwest
Fri 6/1910:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 3/19![Southwest logo]()
$644
This Delta deal was found by Cheapflights users on 3/18. 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.
Sat 4/115:59 pm
ORD
- SJD
2 stops15h 41m
Delta
Sat 4/182:27 pm
SJD
- ORD
1 stop7h 48m
Delta
Deal found 3/18![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 3/19. 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.
Wed 5/67:30 am
MDW
- SJD
1 stop7h 55m
Southwest
Sun 5/103:05 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 3/19![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 3/19. 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.
Fri 4/246:00 am
MDW
- SJD
1 stop9h 04m
Delta
Tue 4/286:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/19![Delta logo]()
$521
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:00 am
MDW
- SJD
2 stops9h 10m
Southwest
Sun 6/1412:20 pm
SJD
- MDW
1 stop9h 25m
Southwest
Deal found 3/15![Southwest logo]()
$674
This Southwest deal was found by Cheapflights users on 3/19. 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.
Wed 6/176:30 am
MDW
- SJD
2 stops9h 50m
Southwest
Sun 6/211:55 pm
SJD
- MDW
1 stop13h 15m
Southwest
Deal found 3/19![Southwest logo]()
$684
This Southwest deal was found by Cheapflights users on 3/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:30 am
MDW
- SJD
2 stops8h 55m
Southwest
Sun 6/71:55 pm
SJD
- MDW
1 stop13h 15m
Southwest
Deal found 3/15![Southwest logo]()
$699
This Delta deal was found by Cheapflights users on 3/16. 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.
Tue 5/56:00 am
MDW
- SJD
1 stop7h 31m
Delta
Sun 5/106:02 am
SJD
- MDW
2 stops13h 07m
Delta
Deal found 3/16![Delta logo]()
$659
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/236:00 am
MDW
- SJD
1 stop9h 04m
Delta
Tue 4/2812:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/17![Delta logo]()
$740
This Delta deal was found by Cheapflights users on 3/16. 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.
Fri 4/2412:52 pm
MDW
- SJD
2 stops11h 38m
Delta
Mon 4/276:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/16![Delta logo]()
$765
Last-minute flights from Chicago to Cabo San LucasDiscover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated March 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated March 20, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:15 am
ORD
- SJD
1 stop17h 10m
Viva
Sun 3/296:45 am
SJD
- ORD
1 stop15h 00m
Viva
Deal found 3/16![Viva logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 3/241:15 am
ORD
- SJD
1 stop17h 10m
Multiple Airlines
Sun 3/298:40 am
SJD
- ORD
2 stops28h 26m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$546
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/301:05 pm
ORD
- SJD
1 stop25h 20m
Viva
Sun 4/128:15 pm
SJD
- ORD
1 stop26h 30m
Viva
Deal found 3/16![Viva logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Mon 3/301:49 pm
ORD
- SJD
1 stop27h 03m
Multiple Airlines
Sun 4/52:30 pm
SJD
- ORD
2 stops31h 29m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 3/301:49 pm
ORD
- SJD
1 stop27h 03m
Multiple Airlines
Mon 4/610:40 am
SJD
- ORD
1 stop11h 19m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$500
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Mon 3/301:05 pm
ORD
- SJD
1 stop27h 47m
Multiple Airlines
Sun 4/127:47 pm
SJD
- ORD
2 stops26h 58m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 3/15. 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.
Fri 4/106:00 am
MDW
- SJD
1 stop9h 14m
Delta
Fri 4/176:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/15![Delta logo]()
$521
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Fri 4/1712:25 pm
SJD
- MDW
1 stop7h 55m
Southwest
Deal found 3/17![Southwest logo]()
$519
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:30 am
MDW
- SJD
2 stops8h 55m
Southwest
Tue 4/2112:25 pm
SJD
- MDW
1 stop8h 55m
Southwest
Deal found 3/17![Southwest logo]()
$524
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 4/156:00 am
MDW
- SJD
1 stop9h 04m
Delta
Wed 4/226:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/15![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:55 am
MDW
- SJD
1 stop8h 30m
Southwest
Thu 4/2312:25 pm
SJD
- MDW
2 stops9h 15m
Southwest
Deal found 3/17![Southwest logo]()
$536
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 4/257:45 am
MDW
- SJD
1 stop7h 40m
Southwest
Sat 5/211:35 am
SJD
- MDW
1 stop9h 10m
Southwest
Deal found 3/16![Southwest logo]()
$555
One-way flights from Chicago to Cabo San LucasSearch for one-way flight options from Chicago to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated March 20, 2026.
Search for one-way flight options from Chicago to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated March 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Mon 4/132:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Deal found 3/17![Volaris logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Tue 4/141:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 3/15![Volaris logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/152:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 3/17![Volaris logo]()
$114
This Super.com deal was found by Cheapflights users on 3/15. 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.
Sun 6/142:19 am
ORD
- SJD
1 stop11h 10m
Volaris
Deal found 3/15![Volaris logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 3/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/19![Volaris logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 3/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/19![Volaris logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/18![Volaris logo]()
$139
This Mytrip deal was found by Cheapflights users on 3/18. 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.
Tue 4/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/18![Volaris logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Tue 5/193:07 pm
MDW
- SJD
2 stops41h 08m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$193
This Delta deal was found by Cheapflights users on 3/16. 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 5/176:23 am
MDW
- SJD
2 stops17h 55m
Delta
Deal found 3/16![Delta logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/176:15 am
MDW
- SJD
2 stops31h 19m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 5/126:00 am
MDW
- SJD
3 stops50h 15m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$210
Find flight deals from Chicago to Cabo San Lucas
Keep the following information in mind while searching for Chicago to Cabo San Lucas flight deals. Data was last updated March 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $420 (Kiwi.com) |
One-way from | $98 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $726 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 March 20, 2026.
Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/10
7:59 pm-11:34 am
1 stop17h 35m
San José del Cabo Los Cabos
Fri 4/17
2:30 pm-7:02 pm
2 stops26h 32m
$436
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/10
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Fri 4/17
7:47 pm-5:52 am
1 stop8h 05m
$457
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 4/9
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sun 4/12
7:47 pm-5:52 am
1 stop8h 05m
$458
Quickest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 4/8
8:40 am-11:25 am
Nonstop4h 45m
San José del Cabo Los Cabos
Wed 4/15
11:52 am-6:09 pm
Nonstop4h 17m
$461
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 4/15
7:10 am-5:49 pm
2 stops12h 39m
San José del Cabo Los Cabos
Wed 4/22
6:01 am-8:16 pm
2 stops12h 15m
$476
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/15
6:24 am-5:48 pm
2 stops13h 24m
San José del Cabo Los Cabos
Wed 5/20
10:24 am-12:10 am
1 stop11h 46m
$489
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 5/5
5:15 am-5:48 pm
2 stops14h 33m
San José del Cabo Los Cabos
Sun 5/10
10:24 am-12:10 am
1 stop11h 46m
$489
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 5/11
10:24 am-10:28 pm
2 stops14h 04m
San José del Cabo Los Cabos
Sun 5/17
2:36 pm-12:10 am
1 stop7h 34m
$489
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 5/6
9:50 am-10:18 pm
2 stops14h 28m
San José del Cabo Los Cabos
Sun 5/10
10:24 am-12:10 am
1 stop11h 46m
$489
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 4/8
8:40 am-11:25 am
Nonstop4h 45m
San José del Cabo Los Cabos
Mon 4/13
11:52 am-6:09 pm
Nonstop4h 17m
$506
Showing 1-10 of 39 resultsSorted by cheapest first
Best time to book a flight from Chicago to Cabo San Lucas
Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Chicago with our price prediction graph.
ORD-SJD
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Cabo San Lucas
CHI-C4B
ORD-SJD
MDW-SJD
How far ahead should I book a flight from Chicago to Cabo San Lucas?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Cabo San Lucas. Price data was last updated on March 13, 2026.
Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Cabo San Lucas. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Cabo San Lucas?
Currently, March is the cheapest month in which you can book a flight from Chicago to Cabo San Lucas (average of $263). Flying from Chicago to Cabo San Lucas in October is currently the most expensive (average of $397). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to C4B?
Find hourly flight availability from Chicago to Cabo San Lucas. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 20, 2026.
When flying from Chicago to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Cabo San Lucas
Explore weekly flight availability from Chicago to Cabo San Lucas. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 20, 2026.
The most flights from CHI to C4B are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Chicago 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 March 20, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Cabo San Lucas 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.
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago to Cabo San Lucas
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Cabo San Lucas by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Cabo San Lucas by cabin class
Find flights from Chicago to Cabo San Lucas, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Cabo San Lucas flights
Browse other Chicago and Cabo San Lucas flight options. Last updated on March 20, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on March 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Cabo San Lucas flights
Consider these flights traveling from Chicago to Cabo San Lucas.
Top 6 airlines flying from Chicago to Cabo San Lucas
Discover the top 6 airlines that operate flights from Chicago 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 March 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$393 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$391 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$415 | Average$619 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$609 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$655 | FlexibilityNo cancel fee | On-time63% |