$116+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jun 1 — Jun 81
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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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 May 2, 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 May 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/22:53 am
ORD
- SJD
1 stop7h 23m
Multiple Airlines
Sun 6/78:20 am
SJD
- ORD
1 stop13h 35m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$371
This FlightHub deal was found by Cheapflights users on 4/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 10/27:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/28![Volaris logo]()
$373
This Viva deal was found by Cheapflights users on 4/28. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:30 pm
ORD
- SJD
1 stop25h 55m
Viva
Sat 9/261:10 pm
SJD
- ORD
1 stop8h 55m
Viva
Deal found 4/28![Viva logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Wed 6/102:20 pm
SJD
- ORD
2 stops31h 35m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$375
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/132:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 7/197:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/1![Volaris logo]()
$376
This FlightHub deal was found by Cheapflights users on 4/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 6/2212:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 4/28![Volaris logo]()
$377
This Justfly.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 6/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/29![Volaris logo]()
$379
This Super.com deal was found by Cheapflights users on 4/28. 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 5/242:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Fri 5/297:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/28![Volaris logo]()
$380
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/72:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 6/147:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/29![Volaris logo]()
$381
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/132:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Mon 7/203:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/30![Volaris logo]()
$382
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/30![Volaris logo]()
$383
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Sun 6/148:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 4/27![Volaris logo]()
$448
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 May 2, 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 May 2, 2026.
This Volaris deal was found by Cheapflights users on 4/28. 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 6/272:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Fri 7/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 4/28![Volaris logo]()
$432
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 7/296:00 am
ORD
- SJD
1 stop11h 18m
Alaska Airlines
Tue 8/42:07 pm
SJD
- ORD
1 stop21h 14m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$576
This Viva deal was found by Cheapflights users on 5/2. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:20 pm
ORD
- SJD
1 stop26h 05m
Viva
Mon 5/258:40 am
SJD
- ORD
1 stop14h 05m
Viva
Deal found 5/2![Viva logo]()
$592
This Delta deal was found by Cheapflights users on 4/27. 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 7/57:35 am
ORD
- SJD
1 stop7h 45m
Delta
Fri 7/102:25 pm
SJD
- ORD
2 stops16h 10m
Delta
Deal found 4/27![Delta logo]()
$607
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:50 am
MDW
- SJD
1 stop7h 30m
Southwest
Mon 7/201:15 pm
SJD
- MDW
1 stop10h 10m
Southwest
Deal found 5/2![Southwest logo]()
$627
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 6/119:10 pm
ORD
- SJD
1 stop12h 51m
American Airlines
Tue 6/1612:48 pm
SJD
- ORD
Nonstop4h 31m
American Airlines
Deal found 4/27![American Airlines logo]()
$637
This Volaris deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 6/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/29![Volaris logo]()
$493
This Volaris deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 5/247:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/30![Volaris logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 7/216:20 am
ORD
- SJD
1 stop8h 37m
Alaska Airlines
Mon 7/2710:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:30 am
ORD
- SJD
2 stops14h 18m
Delta
Thu 5/212:46 pm
SJD
- ORD
1 stop7h 24m
Delta
Deal found 4/30![Delta logo]()
$618
This Southwest deal was found by Cheapflights users on 4/28. 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 6/85:45 am
MDW
- SJD
1 stop7h 15m
Southwest
Thu 6/111:15 pm
SJD
- MDW
1 stop14h 10m
Southwest
Deal found 4/28![Southwest logo]()
$632
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 7/142:20 pm
ORD
- SJD
2 stops21h 51m
Alaska Airlines
Mon 7/2010:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:05 am
ORD
- SJD
2 stops14h 11m
Delta
Tue 6/1610:23 am
SJD
- ORD
1 stop11h 44m
Delta
Deal found 4/27![Delta logo]()
$637
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:25 am
MDW
- SJD
1 stop7h 35m
Southwest
Thu 6/1111:35 am
SJD
- MDW
1 stop10h 20m
Southwest
Deal found 4/29![Southwest logo]()
$652
This Alaska Airlines deal was found by Cheapflights users on 5/1. 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 7/186:20 am
ORD
- SJD
1 stop8h 37m
Alaska Airlines
Sat 7/252:07 pm
SJD
- ORD
1 stop21h 14m
Alaska Airlines
Deal found 5/1![Alaska Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:00 am
MDW
- SJD
2 stops8h 40m
Southwest
Sun 7/1211:05 am
SJD
- MDW
1 stop7h 45m
Southwest
Deal found 5/1![Southwest logo]()
$673
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:40 am
MDW
- SJD
2 stops9h 45m
Southwest
Wed 7/1512:50 pm
SJD
- MDW
1 stop7h 35m
Southwest
Deal found 4/30![Southwest logo]()
$679
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:15 am
MDW
- SJD
2 stops10h 25m
Southwest
Fri 6/1910:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 5/1![Southwest logo]()
$680
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:25 am
MDW
- SJD
1 stop10h 15m
Southwest
Sat 7/182:05 pm
SJD
- MDW
2 stops15h 05m
Southwest
Deal found 5/1![Southwest logo]()
$680
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 5/192:20 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 4/29![Southwest logo]()
$707
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:00 am
MDW
- SJD
2 stops8h 35m
Southwest
Sat 7/251:35 pm
SJD
- MDW
1 stop8h 30m
Southwest
Deal found 5/1![Southwest logo]()
$718
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Fri 5/222:20 pm
SJD
- MDW
1 stop13h 25m
Southwest
Deal found 4/30![Southwest logo]()
$747
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:15 am
MDW
- SJD
2 stops9h 45m
Southwest
Sun 6/72:25 pm
SJD
- MDW
1 stop13h 20m
Southwest
Deal found 5/1![Southwest logo]()
$763
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Tue 5/122:20 pm
SJD
- MDW
1 stop7h 00m
Southwest
Deal found 4/28![Southwest logo]()
$781
Last-minute flights from Chicago to Cabo San LucasDiscover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated May 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated May 2, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 5/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/137:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/2![Volaris logo]()
$399
This FlightHub deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/30![Volaris logo]()
$436
This Gotogate deal was found by Cheapflights users on 4/28. 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.
Fri 5/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 5/157:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/28![Volaris logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/87:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Tue 5/1212:02 pm
SJD
- ORD
2 stops24h 33m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$429
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Fri 5/1512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/1![Volaris logo]()
$448
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/137:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/1![Volaris logo]()
$388
This Super.com deal was found by Cheapflights users on 5/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 5/147:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/2![Volaris logo]()
$451
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/102:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Thu 5/1412:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 4/29![Volaris logo]()
$400
This Mytrip deal was found by Cheapflights users on 5/1. 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 5/168:48 pm
MDW
- SJD
2 stops16h 05m
Volaris
Fri 5/227:47 pm
SJD
- MDW
2 stops21h 33m
Volaris
Deal found 5/1![Volaris logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:48 pm
MDW
- SJD
1 stop17h 37m
Multiple Airlines
Sun 5/246:45 am
SJD
- MDW
1 stop10h 19m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$607
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:55 am
MDW
- SJD
1 stop8h 30m
Southwest
Fri 5/291:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 4/29![Southwest logo]()
$608
This Southwest deal was found by Cheapflights users on 5/2. 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 5/315:10 am
MDW
- SJD
1 stop7h 30m
Southwest
Thu 6/411:35 am
SJD
- MDW
1 stop10h 20m
Southwest
Deal found 5/2![Southwest logo]()
$609
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 May 2, 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 May 2, 2026.
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/216:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Deal found 4/29![Volaris logo]()
$116
This Super.com deal was found by Cheapflights users on 5/2. 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 Super.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
Deal found 5/2![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sat 6/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/1![Volaris logo]()
$126
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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 4/29![Volaris logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/29![Volaris logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 4/29![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/1![Volaris logo]()
$137
This FlightHub deal was found by Cheapflights users on 4/28. 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 FlightHub 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 4/28![Volaris logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/30![Volaris logo]()
$140
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/29![Volaris logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/241:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/1![Volaris logo]()
$143
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/29![Volaris logo]()
$159
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 May 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (Kiwi.com) |
One-way from | $116 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $599 |
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 May 2, 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
Sat 6/27
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Fri 7/3
12:02 pm-11:47 pm
1 stop9h 45m
$432
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 6/3
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Sun 6/7
7:47 pm-5:52 am
1 stop8h 05m
$493
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 5/19
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 5/24
7:47 pm-5:52 am
1 stop8h 05m
$528
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/29
6:00 am-3:18 pm
1 stop11h 18m
San José del Cabo Los Cabos
Tue 8/4
2:07 pm-1:21 pm
1 stop21h 14m
$576
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 7/21
6:20 am-12:57 pm
1 stop8h 37m
San José del Cabo Los Cabos
Mon 7/27
10:45 am-11:36 pm
1 stop10h 51m
$587
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/22
12:20 pm-12:25 pm
1 stop26h 05m
San José del Cabo Los Cabos
Mon 5/25
8:40 am-12:45 am
1 stop14h 05m
$592
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 7/14
2:20 pm-10:11 am
2 stops21h 51m
San José del Cabo Los Cabos
Mon 7/20
10:45 am-11:36 pm
1 stop10h 51m
$592
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 7/5
7:35 am-1:20 pm
1 stop7h 45m
San José del Cabo Los Cabos
Fri 7/10
2:25 pm-8:35 am
2 stops16h 10m
$607
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 5/18
5:30 am-5:48 pm
2 stops14h 18m
San José del Cabo Los Cabos
Thu 5/21
2:46 pm-12:10 am
1 stop7h 24m
$618
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 7/13
6:50 am-12:20 pm
1 stop7h 30m
San José del Cabo Los Cabos
Mon 7/20
1:15 pm-1:25 am
1 stop10h 10m
$627
Showing 1-10 of 45 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 May 2, 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 May 2, 2026.
The most flights from CHI to C4B are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 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 May 2, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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
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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 May 2, 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 May 2, 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 May 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$527 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$387 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$318 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$412 | Average$623 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$618 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$694 | FlexibilityNo cancel fee | On-time63% |