$86+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Mar 5 — Mar 121
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 2 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from Chicago to Cabo San Lucas
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Best
Last-minute
One-way
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 February 3, 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 February 3, 2026.
This Aeromexico deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:10 am
ORD
- SJD
2 stops17h 15m
Aeromexico
Tue 4/146:55 pm
SJD
- ORD
2 stops15h 05m
Aeromexico
Deal found 2/3![Aeromexico logo]()
$476
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJD
1 stop8h 40m
Southwest
Fri 3/61:35 pm
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$476
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:07 pm
ORD
- SJD
2 stops21h 00m
Alaska Airlines
Sat 3/74:50 pm
SJD
- ORD
1 stop18h 21m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$477
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:54 pm
ORD
- SJD
1 stop25h 16m
Alaska Airlines
Wed 2/254:47 pm
SJD
- ORD
2 stops30h 12m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:59 pm
ORD
- SJD
2 stops15h 41m
Delta
Wed 2/184:56 pm
SJD
- ORD
2 stops14h 44m
Delta
Deal found 2/2![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJD
1 stop9h 09m
Delta
Wed 2/251:45 pm
SJD
- MDW
1 stop7h 46m
Delta
Deal found 2/2![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:19 am
ORD
- SJD
2 stops13h 06m
Delta
Sat 5/910:20 am
SJD
- ORD
2 stops11h 39m
Delta
Deal found 2/2![Delta logo]()
$480
This Aeromexico deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:46 am
MDW
- SJD
2 stops13h 39m
Aeromexico
Wed 5/1311:36 am
SJD
- MDW
1 stop7h 33m
Aeromexico
Deal found 2/1![Aeromexico logo]()
$480
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:40 am
ORD
- SJD
1 stop7h 02m
United Airlines
Wed 3/1111:50 am
SJD
- ORD
Nonstop4h 09m
United Airlines
Deal found 2/1![United Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:50 am
ORD
- SJD
Nonstop4h 46m
American Airlines
Sun 3/151:36 pm
SJD
- ORD
Nonstop4h 19m
American Airlines
Deal found 2/1![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:40 pm
MDW
- SJD
2 stops15h 00m
Delta
Tue 2/249:35 am
SJD
- MDW
2 stops11h 58m
Delta
Deal found 1/31![Delta logo]()
$482
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:00 am
ORD
- SJD
3 stops29h 36m
Volaris
Tue 2/1012:11 pm
SJD
- ORD
1 stop9h 18m
Volaris
Deal found 2/2![Volaris logo]()
$483
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 February 3, 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 February 3, 2026.
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:54 pm
ORD
- SJD
1 stop8h 33m
Delta
Tue 2/244:56 pm
SJD
- ORD
2 stops14h 44m
Delta
Deal found 2/2![Delta logo]()
$479
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:00 am
ORD
- SJD
1 stop7h 10m
United Airlines
Sun 3/1511:50 am
SJD
- ORD
Nonstop4h 09m
United Airlines
Deal found 2/2![United Airlines logo]()
$481
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:00 am
ORD
- SJD
1 stop9h 36m
Alaska Airlines
Tue 6/24:39 pm
SJD
- ORD
2 stops24h 07m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 am
MDW
- SJD
1 stop8h 15m
Southwest
Tue 3/1712:10 pm
SJD
- MDW
1 stop7h 05m
Southwest
Deal found 2/2![Southwest logo]()
$543
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:40 pm
MDW
- SJD
2 stops15h 00m
Delta
Tue 2/249:35 am
SJD
- MDW
2 stops11h 58m
Delta
Deal found 2/1![Delta logo]()
$484
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Wed 4/1511:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 2/1![United Airlines logo]()
$489
This Alaska Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:52 pm
ORD
- SJD
2 stops21h 37m
Alaska Airlines
Mon 5/410:41 am
SJD
- ORD
1 stop11h 02m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:10 pm
ORD
- SJD
1 stop17h 45m
Delta
Tue 4/72:19 pm
SJD
- ORD
1 stop16h 11m
Delta
Deal found 2/2![Delta logo]()
$498
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:20 am
ORD
- SJD
1 stop29h 21m
Alaska Airlines
Sat 2/283:16 pm
SJD
- ORD
2 stops31h 43m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$506
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:05 am
MDW
- SJD
1 stop8h 15m
Southwest
Mon 3/1612:15 pm
SJD
- MDW
1 stop7h 15m
Southwest
Deal found 2/2![Southwest logo]()
$588
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:00 am
ORD
- SJD
1 stop10h 07m
Alaska Airlines
Sun 3/2210:40 am
SJD
- ORD
1 stop11h 19m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJD
1 stop9h 09m
Delta
Sat 2/281:45 pm
SJD
- MDW
1 stop7h 46m
Delta
Deal found 1/31![Delta logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/162:07 pm
ORD
- SJD
2 stops23h 34m
Alaska Airlines
Fri 3/2010:40 am
SJD
- ORD
1 stop11h 19m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- SJD
1 stop9h 04m
Delta
Sat 5/1611:36 am
SJD
- MDW
1 stop7h 33m
Delta
Deal found 1/31![Delta logo]()
$525
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:59 pm
ORD
- SJD
2 stops19h 41m
Alaska Airlines
Mon 4/612:44 pm
SJD
- ORD
1 stop15h 55m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
MDW
- SJD
1 stop9h 14m
Delta
Fri 4/108:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 2/2![Delta logo]()
$548
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:40 am
ORD
- SJD
1 stop30h 01m
Alaska Airlines
Sun 3/2210:40 am
SJD
- ORD
1 stop11h 19m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:00 am
MDW
- SJD
1 stop7h 30m
Delta
Tue 4/71:32 pm
SJD
- MDW
1 stop17h 18m
Delta
Deal found 2/2![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:00 am
MDW
- SJD
2 stops12h 37m
Delta
Thu 2/264:56 pm
SJD
- MDW
2 stops14h 58m
Delta
Deal found 2/2![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:40 pm
MDW
- SJD
2 stops15h 00m
Delta
Sat 3/79:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 2/1![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- SJD
1 stop7h 31m
Delta
Sat 5/212:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 2/1![Delta logo]()
$585
Last-minute flights from Chicago to Cabo San LucasDiscover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated February 3, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:00 am
ORD
- SJD
3 stops29h 36m
Volaris
Tue 2/1012:11 pm
SJD
- ORD
1 stop9h 18m
Volaris
Deal found 2/2![Volaris logo]()
$483
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/612:59 pm
ORD
- SJD
2 stops27h 20m
Volaris
Mon 2/94:34 pm
SJD
- ORD
2 stops11h 02m
Volaris
Deal found 2/2![Volaris logo]()
$476
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:59 pm
ORD
- SJD
2 stops15h 41m
Delta
Wed 2/184:56 pm
SJD
- ORD
2 stops14h 44m
Delta
Deal found 2/2![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:54 pm
ORD
- SJD
1 stop8h 33m
Delta
Tue 2/249:35 am
SJD
- ORD
2 stops13h 21m
Delta
Deal found 1/31![Delta logo]()
$478
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:40 pm
MDW
- SJD
2 stops15h 00m
Delta
Tue 2/249:35 am
SJD
- MDW
2 stops11h 58m
Delta
Deal found 1/31![Delta logo]()
$482
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SJD
2 stops12h 37m
Delta
Wed 2/251:45 pm
SJD
- MDW
1 stop7h 46m
Delta
Deal found 2/2![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:45 am
ORD
- SJD
2 stops15h 30m
Delta
Tue 2/244:56 pm
SJD
- ORD
2 stops14h 44m
Delta
Deal found 2/3![Delta logo]()
$484
This Alaska Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:07 pm
ORD
- SJD
2 stops21h 00m
Alaska Airlines
Sat 3/74:50 pm
SJD
- ORD
1 stop18h 21m
Alaska Airlines
Deal found 2/1![Alaska Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- SJD
1 stop8h 40m
Southwest
Fri 3/61:35 pm
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$476
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:00 am
ORD
- SJD
1 stop8h 42m
United Airlines
Wed 3/1111:50 am
SJD
- ORD
Nonstop4h 09m
United Airlines
Deal found 2/1![United Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:50 am
ORD
- SJD
Nonstop4h 46m
American Airlines
Sun 3/151:36 pm
SJD
- ORD
Nonstop4h 19m
American Airlines
Deal found 2/1![American Airlines logo]()
$482
This Gotogate deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:55 am
ORD
- SJD
1 stop16h 30m
Viva
Mon 3/235:05 pm
SJD
- ORD
1 stop29h 20m
Viva
Deal found 2/2![Viva logo]()
$480
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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/1![Volaris logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:23 am
ORD
- SJD
1 stop9h 57m
Volaris
Deal found 2/1![Volaris logo]()
$104
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 2/1![Volaris logo]()
$109
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:59 pm
ORD
- SJD
1 stop12h 31m
Volaris
Deal found 2/1![Volaris logo]()
$110
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip 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 2/2![Volaris logo]()
$111
This Mytrip deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 1/31![Volaris logo]()
$113
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:23 am
ORD
- SJD
1 stop9h 57m
Volaris
Deal found 2/1![Volaris logo]()
$114
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/2![Volaris logo]()
$115
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/1![Volaris logo]()
$116
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/198:53 pm
ORD
- SJD
2 stops20h 11m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 1/31![Volaris logo]()
$121
This Trip.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:53 pm
MDW
- SJD
1 stop18h 22m
Frontier
Deal found 2/1![Frontier logo]()
$138
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $476 (Aeromexico) |
One-way from | $86 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $665 |
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 February 3, 2026.
Use the filters below to find and compare flights from Chicago to Cabo San Lucas that are best for you.
Fly from
Chicago
Fly to
Cabo San Lucas
Route
Depart
Return
Price
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 2/19
2:54 pm-10:27 pm
1 stop8h 33m
San José del Cabo Los Cabos
Tue 2/24
4:56 pm-8:40 am
2 stops14h 44m
$479
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 3/8
7:00 am-12:10 pm
1 stop7h 10m
San José del Cabo Los Cabos
Sun 3/15
11:50 am-5:59 pm
Nonstop4h 09m
$481
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 5/26
9:00 am-4:36 pm
1 stop9h 36m
San José del Cabo Los Cabos
Tue 6/2
4:39 pm-6:46 pm
2 stops24h 07m
$482
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 2/20
6:40 pm-8:40 am
2 stops15h 00m
San José del Cabo Los Cabos
Tue 2/24
9:35 am-10:33 pm
2 stops11h 58m
$484
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/10
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
$489
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/1
3:52 pm-11:29 am
2 stops21h 37m
San José del Cabo Los Cabos
Mon 5/4
10:41 am-11:43 pm
1 stop11h 02m
$494
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 3/29
7:10 pm-10:55 am
1 stop17h 45m
San José del Cabo Los Cabos
Tue 4/7
2:19 pm-8:30 am
1 stop16h 11m
$498
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 2/21
8:20 am-12:41 pm
1 stop29h 21m
San José del Cabo Los Cabos
Sat 2/28
3:16 pm-11:59 pm
2 stops31h 43m
$506
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 3/13
7:00 am-3:07 pm
1 stop10h 07m
San José del Cabo Los Cabos
Sun 3/22
10:40 am-11:59 pm
1 stop11h 19m
$511
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 3/16
2:07 pm-11:41 am
2 stops23h 34m
San José del Cabo Los Cabos
Fri 3/20
10:40 am-11:59 pm
1 stop11h 19m
$511
Showing 1-10 of 42 results
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 January 30, 2026.
Booking 2 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 $268). Flying from Chicago to Cabo San Lucas in October is currently the most expensive (average of $390). 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 February 3, 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 February 3, 2026.
The most flights from CHI to C4B are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 February 3, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Chicago to Cabo San Lucas
See prices for flight routes from nearby airports that may be better suited for you.
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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$252 | Average$385 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$268 | Average$355 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$543 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$417 | Average$606 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$418 | Average$640 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$485 | Average$696 | FlexibilityNo cancel fee | On-time63% |