$117+ 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jul 21 — Jul 281
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 27 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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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 June 21, 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 June 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 7/67:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Tue 6/307:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 7/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 8/247:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/16![Volaris logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Wed 7/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/19![Volaris logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Mon 6/227:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 6/243:36 pm
SJD
- ORD
1 stop8h 45m
Volaris
Deal found 6/18![Volaris logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Mon 6/292:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Fri 7/32:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sat 7/43:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/17![Volaris logo]()
$388
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Thu 9/107:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 9/1512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/18![Volaris logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 6/237:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 6/263:36 pm
SJD
- ORD
1 stop8h 45m
Volaris
Deal found 6/19![Volaris logo]()
$390
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 June 21, 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 June 21, 2026.
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/92:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Thu 8/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/16![Volaris logo]()
$458
This Southwest deal was found by Cheapflights users on 6/21. 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 10/235:10 am
MDW
- SJD
2 stops10h 30m
Southwest
Tue 10/2711:05 am
SJD
- MDW
1 stop7h 55m
Southwest
Deal found 6/21![Southwest logo]()
$618
This Alaska Airlines deal was found by Cheapflights users on 6/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
ORD
- SJD
1 stop11h 24m
Alaska Airlines
Sat 9/197:02 pm
SJD
- ORD
2 stops26h 57m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$628
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:05 am
MDW
- SJD
1 stop7h 02m
Delta
Sat 9/196:15 am
SJD
- MDW
2 stops14h 30m
Delta
Deal found 6/20![Delta logo]()
$704
This Volaris deal was found by Cheapflights users on 6/19. 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.
Tue 8/112:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 8/163:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/19![Volaris logo]()
$482
This Volaris deal was found by Cheapflights users on 6/17. 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.
Fri 7/106:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Wed 7/153:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/17![Volaris logo]()
$495
This Volaris deal was found by Cheapflights users on 6/20. 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.
Sat 8/82:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 8/163:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/20![Volaris logo]()
$496
This Southwest deal was found by Cheapflights users on 6/16. 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 7/147:00 am
MDW
- SJD
1 stop9h 15m
Southwest
Tue 7/2111:35 am
SJD
- MDW
1 stop9h 35m
Southwest
Deal found 6/16![Southwest logo]()
$654
This Alaska Airlines deal was found by Cheapflights users on 6/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:20 pm
ORD
- SJD
2 stops23h 18m
Alaska Airlines
Sat 8/112:38 pm
SJD
- ORD
1 stop14h 22m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$654
This Volaris deal was found by Cheapflights users on 6/16. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Wed 8/53:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/16![Volaris logo]()
$508
This Southwest deal was found by Cheapflights users on 6/19. 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.
Fri 7/106:40 am
MDW
- SJD
2 stops8h 45m
Southwest
Fri 7/179:45 am
SJD
- MDW
2 stops10h 20m
Southwest
Deal found 6/19![Southwest logo]()
$673
This Volaris deal was found by Cheapflights users on 6/18. 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.
Sat 6/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Fri 7/33:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$513
This Volaris deal was found by Cheapflights users on 6/18. 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.
Wed 6/241:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 6/297:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$513
This Southwest deal was found by Cheapflights users on 6/21. 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 9/126:50 am
MDW
- SJD
1 stop6h 15m
Southwest
Sat 9/1911:35 am
SJD
- MDW
2 stops9h 50m
Southwest
Deal found 6/21![Southwest logo]()
$698
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 11/55:10 am
MDW
- SJD
1 stop10h 05m
Southwest
Sun 11/83:10 pm
SJD
- MDW
1 stop13h 30m
Southwest
Deal found 6/16![Southwest logo]()
$704
This Volaris deal was found by Cheapflights users on 6/17. 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.
Fri 7/36:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Sun 7/53:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/17![Volaris logo]()
$592
This Southwest deal was found by Cheapflights users on 6/17. 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.
Thu 8/277:25 am
MDW
- SJD
1 stop7h 25m
Southwest
Sun 8/302:05 pm
SJD
- MDW
1 stop8h 20m
Southwest
Deal found 6/17![Southwest logo]()
$726
This Volaris deal was found by Cheapflights users on 6/21. 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 7/212:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 7/267:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/21![Volaris logo]()
$607
This Volaris deal was found by Cheapflights users on 6/18. 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.
Sat 6/274:03 am
ORD
- SJD
1 stop12h 48m
Volaris
Thu 7/212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/18![Volaris logo]()
$623
Last-minute flights from Chicago to Cabo San LucasDiscover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated June 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 7/67:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 7/83:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Thu 7/912:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/18![Volaris logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/274:03 am
ORD
- SJD
1 stop9h 26m
Volaris
Mon 7/67:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 7/57:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 6/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Mon 6/292:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Tue 6/307:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 7/53:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/18![Volaris logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Tue 6/302:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 7/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/18![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Wed 7/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/19![Volaris logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 7/153:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/21![Volaris logo]()
$394
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 June 21, 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 June 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/196:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 6/21![Volaris logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/171:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/21![Volaris logo]()
$120
This Mytrip deal was found by Cheapflights users on 6/19. 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.
Wed 7/292:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 6/19![Volaris logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 9/131:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/18![Volaris logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/21![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Tue 9/157:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/20![Volaris logo]()
$125
This Super.com deal was found by Cheapflights users on 6/17. 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.
Sat 7/47:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/17![Volaris logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sun 7/122:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 6/19![Volaris logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 7/151:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/21![Volaris logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Thu 7/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/17![Volaris logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Fri 7/176:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 6/19![Volaris logo]()
$130
This Trip.com deal was found by Cheapflights users on 6/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 6/17![Volaris logo]()
$179
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (Kiwi.com) |
One-way from | $117 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $597 |
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 June 21, 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
Sun 8/9
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Thu 8/13
3:36 pm-12:55 am
1 stop7h 19m
$458
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 8/11
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Sun 8/16
3:36 pm-12:55 am
1 stop7h 19m
$482
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 7/10
6:21 am-2:51 pm
1 stop10h 30m
San José del Cabo Los Cabos
Wed 7/15
3:36 pm-12:55 am
1 stop7h 19m
$495
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 8/8
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Sun 8/16
3:36 pm-12:55 am
1 stop7h 19m
$496
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 7/28
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Wed 8/5
3:36 pm-12:55 am
1 stop7h 19m
$508
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 6/27
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Fri 7/3
3:36 pm-12:55 am
1 stop7h 19m
$513
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 6/24
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Mon 6/29
7:47 pm-5:52 am
1 stop8h 05m
$513
Quickest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 7/3
6:21 am-11:29 am
1 stop7h 08m
San José del Cabo Los Cabos
Sun 7/5
3:36 pm-12:55 am
1 stop7h 19m
$592
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 7/21
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Sun 7/26
7:47 pm-5:52 am
1 stop8h 05m
$607
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 10/23
5:10 am-1:40 pm
2 stops10h 30m
San José del Cabo Los Cabos
Tue 10/27
11:05 am-9:00 pm
1 stop7h 55m
$618
Showing 1-10 of 43 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
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 June 21, 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.
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 June 21, 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
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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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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 June 21, 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 June 21, 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 5 airlines flying from Chicago to Cabo San Lucas
Discover the top 5 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 June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$389 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$223 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$417 | Average$642 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$419 | Average$639 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |