$118+ Cheap flights from Chicago (CHI) to Los Cabos
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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jun 10 — Jun 171
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Los Cabos with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to Los CabosExplore the most affordable flight options available from Chicago to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.
Explore the most affordable flight options available from Chicago to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.
This FlightHub deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/157:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/2012:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/6![Volaris logo]()
$383
This Super.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 8/317:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/6![Volaris logo]()
$384
This Super.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/297:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 6/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/7![Volaris logo]()
$385
This Viva deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 11/2311:30 am
ORD
- SJD
1 stop25h 54m
Viva
Mon 11/308:15 am
SJD
- ORD
1 stop13h 30m
Viva
Deal found 5/11![Viva logo]()
$386
This Super.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 6/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/7![Volaris logo]()
$387
This Super.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/301:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Fri 6/512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/7![Volaris logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Sun 6/78:20 am
SJD
- ORD
1 stop13h 35m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$389
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/297:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 7/1212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/11![Volaris logo]()
$390
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/11![Volaris logo]()
$391
This Super.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Fri 7/37:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/8![Volaris logo]()
$393
This FlightHub deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/171:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 6/2212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/8![Volaris logo]()
$394
This Super.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Sun 7/198:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 5/8![Volaris logo]()
$502
Best flights from Chicago to Los CabosDiscover carefully curated flight deals from Chicago to Los Cabos that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 11, 2026.
Discover carefully curated flight deals from Chicago to Los Cabos that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 11, 2026.
This Viva deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Wed 6/312:30 pm
ORD
- SJD
1 stop19h 50m
Viva
Wed 6/108:20 am
SJD
- ORD
1 stop13h 35m
Viva
Deal found 5/7![Viva logo]()
$396
This Volaris deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/167:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/10![Volaris logo]()
$478
This Alaska Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/286:00 am
ORD
- SJD
1 stop9h 32m
Alaska Airlines
Fri 5/2911:20 am
SJD
- ORD
1 stop17h 00m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:40 am
ORD
- SJD
2 stops17h 50m
Delta
Wed 8/126:04 am
SJD
- ORD
2 stops15h 54m
Delta
Deal found 5/9![Delta logo]()
$519
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/166:40 am
MDW
- SJD
2 stops9h 00m
Southwest
Thu 7/239:45 am
SJD
- MDW
2 stops10h 10m
Southwest
Deal found 5/9![Southwest logo]()
$659
This Volaris deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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.
Sun 7/192:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Mon 7/2712:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/10![Volaris logo]()
$513
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 8/46:05 am
MDW
- SJD
1 stop7h 02m
Delta
Tue 8/1110:05 am
SJD
- MDW
2 stops21h 54m
Delta
Deal found 5/9![Delta logo]()
$519
This Volaris deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 6/1512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/9![Volaris logo]()
$514
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:05 am
MDW
- SJD
1 stop7h 02m
Delta
Thu 8/1312:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/9![Delta logo]()
$519
This Alaska Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/266:20 am
ORD
- SJD
1 stop8h 37m
Alaska Airlines
Sun 8/210:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$588
This Volaris deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/31:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 6/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/10![Volaris logo]()
$544
This Alaska Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 8/66:00 am
ORD
- SJD
2 stops13h 38m
Alaska Airlines
Fri 8/710:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 5/9![Alaska Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/106:00 am
MDW
- SJD
1 stop7h 11m
Delta
Wed 7/1512:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 5/9![Delta logo]()
$564
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/266:50 am
MDW
- SJD
1 stop7h 30m
Southwest
Fri 7/310:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 5/8![Southwest logo]()
$683
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:25 am
ORD
- SJD
2 stops10h 53m
Delta
Sun 8/162:44 pm
SJD
- ORD
2 stops15h 56m
Delta
Deal found 5/10![Delta logo]()
$569
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/177:45 am
MDW
- SJD
2 stops7h 55m
Southwest
Wed 5/201:05 pm
SJD
- MDW
1 stop8h 00m
Southwest
Deal found 5/8![Southwest logo]()
$698
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:20 am
MDW
- SJD
1 stop6h 25m
Southwest
Mon 6/2910:40 am
SJD
- MDW
1 stop10h 45m
Southwest
Deal found 5/6![Southwest logo]()
$720
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:07 am
ORD
- SJD
2 stops17h 21m
Delta
Fri 5/296:07 am
SJD
- ORD
2 stops15h 52m
Delta
Deal found 5/7![Delta logo]()
$629
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/277:20 am
MDW
- SJD
1 stop8h 10m
Southwest
Sat 7/411:35 am
SJD
- MDW
2 stops15h 50m
Southwest
Deal found 5/6![Southwest logo]()
$735
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/248:45 pm
MDW
- SJD
2 stops16h 00m
Southwest
Sat 5/301:35 pm
SJD
- MDW
2 stops13h 25m
Southwest
Deal found 5/10![Southwest logo]()
$753
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/106:00 am
MDW
- SJD
1 stop7h 11m
Delta
Mon 7/1312:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 5/7![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 8/46:05 am
MDW
- SJD
1 stop7h 02m
Delta
Mon 8/1012:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/9![Delta logo]()
$733
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated May 11, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/151:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 5/1812:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/8![Volaris logo]()
$473
This Gotogate deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/197:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/11![Volaris logo]()
$410
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/167:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/2312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/11![Volaris logo]()
$425
This Mytrip deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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
Mon 5/187:37 pm
SJD
- MDW
2 stops17h 14m
Volaris
Deal found 5/8![Volaris logo]()
$635
This Super.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/177:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/2012:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/8![Volaris logo]()
$432
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/176:55 am
MDW
- SJD
1 stop8h 45m
Southwest
Wed 5/201:05 pm
SJD
- MDW
1 stop8h 00m
Southwest
Deal found 5/8![Southwest logo]()
$658
This FlightHub deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Wed 5/277:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/10![Volaris logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/197:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/274:49 pm
SJD
- ORD
2 stops17h 20m
Volaris
Deal found 5/10![Volaris logo]()
$445
This FlightHub deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 5/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 5/2412:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/9![Volaris logo]()
$489
This FlightHub deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/217:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/2612:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/8![Volaris logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
Tue 5/267:47 pm
SJD
- MDW
2 stops21h 17m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$610
This Mytrip deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/218:48 pm
MDW
- SJD
2 stops18h 32m
Volaris
Tue 5/267:47 pm
SJD
- MDW
2 stops21h 17m
Volaris
Deal found 5/7![Volaris logo]()
$640
One-way flights from Chicago to Los CabosSearch for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
Search for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
This Super.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/36:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 5/8![Volaris logo]()
$118
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/11![Volaris logo]()
$121
This Super.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/32:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/9![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 5/11![Volaris logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/301:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/8![Volaris logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/202:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/10![Volaris logo]()
$130
This FlightHub deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 10/111:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/8![Volaris logo]()
$131
This Super.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/122:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/7![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/151:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/11![Volaris logo]()
$138
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/167:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/11![Volaris logo]()
$139
This Mytrip deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/88:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/7![Volaris logo]()
$205
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 8/35:10 pm
MDW
- SJD
2 stops21h 24m
Delta
Deal found 5/8![Delta logo]()
$238
Find flight deals from Chicago to Los Cabos
Keep the following information in mind while searching for Chicago to Los Cabos flight deals. Data was last updated May 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $383 (Super.com) |
One-way from | $118 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $616 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Los Cabos 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 11, 2026.
Use the filters below to find and compare flights from Chicago to Los Cabos 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
Wed 6/3
12:30 pm-6:20 am
1 stop19h 50m
San José del Cabo Los Cabos
Wed 6/10
8:20 am-11:55 pm
1 stop13h 35m
$396
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
7:47 pm-5:52 am
1 stop8h 05m
$478
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/28
6:00 am-1:32 pm
1 stop9h 32m
San José del Cabo Los Cabos
Fri 5/29
11:20 am-6:20 am
1 stop17h 00m
$486
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 7/19
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Mon 7/27
12:02 pm-11:47 pm
1 stop9h 45m
$513
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 6/11
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Mon 6/15
12:02 pm-11:47 pm
1 stop9h 45m
$514
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 8/5
6:40 am-10:30 pm
2 stops17h 50m
San José del Cabo Los Cabos
Wed 8/12
6:04 am-11:58 pm
2 stops15h 54m
$519
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 8/4
6:05 am-11:07 am
1 stop7h 02m
San José del Cabo Los Cabos
Tue 8/11
10:05 am-9:59 am
2 stops21h 54m
$519
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 8/9
6:05 am-11:07 am
1 stop7h 02m
San José del Cabo Los Cabos
Thu 8/13
12:12 pm-10:36 pm
1 stop8h 24m
$519
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 6/3
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 6/7
7:47 pm-5:52 am
1 stop8h 05m
$544
Quickest round-trip
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 7/10
6:00 am-11:11 am
1 stop7h 11m
San José del Cabo Los Cabos
Wed 7/15
12:16 pm-10:15 pm
1 stop7h 59m
$564
Showing 1-10 of 44 resultsSorted by cheapest first
Best time to book a flight from Chicago to Los Cabos
Have a flexible travel schedule? Discover the best time to fly to Los Cabos 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 Los Cabos
CHI-zzKPG
ORD-SJD
MDW-SJD
How far ahead should I book a flight from Chicago to Los Cabos?
The best time to book flights from Chicago to Los Cabos is 32 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Los Cabos?
Currently, February is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $131). Flying from Chicago to Los Cabos in March is currently the most expensive (average of $1,110). 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 KPG?
Find hourly flight availability from Chicago to Los Cabos. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 11, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Los Cabos as you normally would.
Weekly flight availability from Chicago to Los Cabos
Explore weekly flight availability from Chicago to Los Cabos. 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 11, 2026.
The most flights from CHI to zzKPG 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).
Reviews of airlines servicing Los Cabos
Get insights into the airlines that provide service to Los Cabos. 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 Los Cabos. Reviews last updated May 11, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Los Cabos to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
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 Los Cabos. 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 Los Cabos
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Los Cabos by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Los Cabos by cabin class
Find flights from Chicago to Los Cabos, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Los Cabos flights
Browse other Chicago and Los Cabos flight options. Last updated on May 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Los Cabos
Discover the top 6 airlines that operate flights from Chicago to Los Cabos. 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 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$543 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$390 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$318 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$413 | Average$624 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$415 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |