$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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Sep 5 — Sep 121
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
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.Cheap flight deals from Chicago to Los Cabos
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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 August 6, 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 August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/47:35 am -
1 stop13h 29m
Wed 10/147:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:35 am -
1 stop13h 29m
Sat 10/37:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/71:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$349
This Super.com deal was found by Cheapflights users on 8/1. 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 8/247:35 am -
1 stop13h 29m
Wed 8/2612:06 pm -
1 stop10h 49m
Deal found 8/1![Volaris logo]()
$350
This FlightHub deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/91:40 am -
1 stop10h 29m
Tue 9/1512:06 pm -
1 stop10h 49m
Deal found 8/4![Volaris logo]()
$351
This Justfly.com deal was found by Cheapflights users on 8/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/1![Volaris logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:40 am -
1 stop10h 29m
Sat 9/123:36 pm -
1 stop7h 19m
Deal found 8/3![Volaris logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$354
This Super.com deal was found by Cheapflights users on 8/1. 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 10/107:35 am -
1 stop13h 29m
Wed 10/147:47 pm -
1 stop8h 05m
Deal found 8/1![Volaris logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:35 am -
1 stop13h 29m
Sat 10/37:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$356
This Booking.com deal was found by Cheapflights users on 8/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:25 pm -
1 stop26h 00m
Wed 9/21:12 pm -
1 stop8h 47m
Deal found 8/3![Viva logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/26:17 pm -
1 stop22h 53m
Fri 11/67:27 am -
1 stop8h 20m
Deal found 8/1![Multiple Airlines logo]()
$529
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 August 6, 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 August 6, 2026.
This Volaris deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/241:40 am -
1 stop10h 29m
Thu 10/112:02 pm -
1 stop9h 45m
Deal found 8/4![Volaris logo]()
$428
This Alaska Airlines deal was found by Cheapflights users on 8/3. 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.
Sun 11/17:56 pm -
2 stops18h 48m
Thu 11/55:03 pm -
2 stops24h 57m
Deal found 8/3![Alaska Airlines logo]()
$586
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:03 am -
Nonstop5h 00m
Thu 11/512:55 pm -
Nonstop4h 16m
Deal found 8/3![United Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:15 am -
1 stop6h 40m
Thu 11/52:45 pm -
2 stops9h 20m
Deal found 8/3![Southwest logo]()
$607
This Delta deal was found by Cheapflights users on 8/2. 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 10/46:05 am -
2 stops13h 30m
Sat 10/106:15 am -
2 stops14h 18m
Deal found 8/2![Delta logo]()
$650
This Volaris deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Mon 11/21:24 am -
1 stop10h 11m
Tue 11/103:30 pm -
1 stop7h 14m
Deal found 8/4![Volaris logo]()
$434
This Volaris deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:40 am -
1 stop10h 29m
Sat 10/243:36 pm -
1 stop7h 19m
Deal found 8/4![Volaris logo]()
$465
This Volaris deal was found by Cheapflights users on 8/3. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:53 am -
1 stop10h 36m
Wed 11/43:30 pm -
1 stop7h 14m
Deal found 8/3![Volaris logo]()
$477
This United Airlines deal was found by Cheapflights users on 8/2. 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 10/48:52 am -
Nonstop4h 33m
Wed 10/711:52 am -
Nonstop4h 15m
Deal found 8/2![United Airlines logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 8/2. 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 10/297:49 pm -
1 stop18h 01m
Thu 11/55:03 pm -
2 stops24h 57m
Deal found 8/2![Alaska Airlines logo]()
$611
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:05 am -
1 stop8h 00m
Tue 10/2011:05 am -
2 stops10h 40m
Deal found 8/3![Southwest logo]()
$612
This Delta deal was found by Cheapflights users on 8/1. 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 9/116:05 am -
1 stop7h 02m
Tue 9/1512:12 pm -
1 stop8h 32m
Deal found 8/1![Delta logo]()
$668
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/75:40 am -
1 stop7h 05m
Thu 9/1011:40 am -
2 stops10h 10m
Deal found 8/5![Southwest logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 8/1. 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.
Wed 10/282:21 pm -
1 stop28h 17m
Wed 11/45:03 pm -
2 stops24h 57m
Deal found 8/1![Alaska Airlines logo]()
$628
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/197:45 am -
Nonstop4h 33m
Thu 9/2411:52 am -
Nonstop4h 15m
Deal found 8/5![United Airlines logo]()
$636
This Alaska Airlines deal was found by Cheapflights users on 8/3. 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 10/307:20 am -
1 stop11h 18m
Fri 11/611:48 am -
2 stops16h 52m
Deal found 8/3![Alaska Airlines logo]()
$639
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/256:00 am -
1 stop9h 50m
Wed 12/22:45 pm -
1 stop7h 20m
Deal found 8/4![Southwest logo]()
$650
This Delta deal was found by Cheapflights users on 8/2. 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 8/246:05 am -
1 stop7h 02m
Mon 8/3112:12 pm -
1 stop8h 24m
Deal found 8/2![Delta logo]()
$755
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 1/235:10 am -
1 stop6h 55m
Tue 1/2612:35 pm -
2 stops9h 25m
Deal found 8/2![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 11/147:35 am -
1 stop7h 45m
Tue 11/172:05 pm -
1 stop9h 05m
Deal found 8/4![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 12/3010:45 pm -
2 stops14h 25m
Wed 1/61:05 pm -
1 stop8h 25m
Deal found 8/5![Southwest logo]()
$655
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:05 am -
2 stops9h 35m
Mon 10/1912:15 pm -
2 stops10h 50m
Deal found 8/3![Southwest logo]()
$682
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated August 6, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/102:53 am -
1 stop10h 36m
Tue 8/187:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:35 am -
1 stop13h 29m
Wed 8/1912:02 pm -
1 stop9h 45m
Deal found 8/5![Volaris logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:35 am -
1 stop13h 29m
Wed 8/197:47 pm -
2 stops50h 08m
Deal found 8/5![Multiple Airlines logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:35 am -
1 stop13h 29m
Tue 8/187:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:35 am -
1 stop13h 29m
Mon 8/177:47 pm -
2 stops22h 28m
Deal found 8/5![Volaris logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:35 am -
1 stop13h 29m
Sun 8/167:47 pm -
2 stops42h 08m
Deal found 8/4![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/137:35 am -
1 stop13h 29m
Tue 8/187:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/137:35 am -
1 stop13h 29m
Mon 8/177:47 pm -
2 stops22h 28m
Deal found 8/5![Volaris logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/142:53 am -
1 stop7h 23m
Sat 8/2212:06 pm -
2 stops33h 02m
Deal found 8/2![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/142:53 am -
1 stop7h 23m
Sat 8/227:47 pm -
1 stop8h 05m
Deal found 8/2![Volaris logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:30 pm -
2 stops21h 21m
Sun 9/61:12 pm -
1 stop27h 52m
Deal found 8/3![Multiple Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/48:23 pm -
1 stop18h 03m
Mon 9/78:05 am -
2 stops32h 00m
Deal found 8/5![Multiple Airlines logo]()
$547
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 August 6, 2026.
Search for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Viva deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Sat 10/32:40 pm -
1 stop19h 03m
Deal found 8/4![Viva logo]()
$118
This Viva deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/55:20 pm -
1 stop16h 23m
Deal found 8/5![Viva logo]()
$130
This Super.com deal was found by Cheapflights users on 8/1. 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 9/51:40 am -
1 stop10h 29m
Deal found 8/1![Volaris logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/51:40 am -
1 stop10h 29m
Deal found 8/5![Volaris logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 10/27:35 am -
1 stop13h 29m
Deal found 8/2![Volaris logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:35 am -
1 stop13h 29m
Deal found 8/3![Volaris logo]()
$139
This iWofly deal was found by Cheapflights users on 8/2. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:53 am -
1 stop10h 36m
Deal found 8/2![Volaris logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 9/281:40 am -
1 stop10h 29m
Deal found 8/1![Volaris logo]()
$143
This CheapOair deal was found by Cheapflights users on 8/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:53 am -
1 stop10h 36m
Deal found 8/2![Volaris logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/302:53 am -
1 stop10h 36m
Deal found 8/2![Volaris logo]()
$145
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/138:49 pm -
1 stop13h 27m
Deal found 8/5![Volaris logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:23 pm -
1 stop18h 03m
Deal found 8/4![Multiple Airlines logo]()
$216
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $347 (Kiwi.com) |
One-way from | $118 (Viva) |
Popular in | March |
Cheapest in | September |
Average price | $605 |
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 August 6, 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 Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Thu 9/24
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Thu 10/1
12:02 pm-11:47 pm
1 stop9h 45m
$428
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Mon 11/2
1:24 am-10:35 am
1 stop10h 11m
San José del Cabo Los Cabos
Tue 11/10
3:30 pm-11:44 pm
1 stop7h 14m
$434
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Fri 10/16
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sat 10/24
3:36 pm-12:55 am
1 stop7h 19m
$465
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Tue 10/27
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Wed 11/4
3:30 pm-11:44 pm
1 stop7h 14m
$477
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sun 11/1
7:56 pm-1:44 pm
2 stops18h 48m
San José del Cabo Los Cabos
Thu 11/5
5:03 pm-7:00 pm
2 stops24h 57m
$586
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sun 11/1
9:03 am-1:03 pm
Nonstop5h 00m
San José del Cabo Los Cabos
Thu 11/5
12:55 pm-6:11 pm
Nonstop4h 16m
$593
Quickest round-trip
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sun 10/4
8:52 am-11:25 am
Nonstop4h 33m
San José del Cabo Los Cabos
Wed 10/7
11:52 am-6:07 pm
Nonstop4h 15m
$593
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sun 11/1
5:15 am-10:55 am
1 stop6h 40m
San José del Cabo Los Cabos
Thu 11/5
2:45 pm-1:05 am
2 stops9h 20m
$607
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Thu 10/29
7:49 pm-11:50 am
1 stop18h 01m
San José del Cabo Los Cabos
Thu 11/5
5:03 pm-7:00 pm
2 stops24h 57m
$611
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 10/13
6:05 am-12:05 pm
1 stop8h 00m
San José del Cabo Los Cabos
Tue 10/20
11:05 am-11:45 pm
2 stops10h 40m
$612
Showing 1-10 of 39 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
What is the cheapest month to book a flight from Chicago to Los Cabos?
Currently, September is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $489). Flying from Chicago to Los Cabos in March is currently the most expensive (average of $693). 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 August 6, 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.
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 16 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.
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 August 6, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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.
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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Complete your trip
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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 August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Los Cabos
Discover the top 4 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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$394 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$417 | Average$648 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$443 | Average$658 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$718 | FlexibilityNo cancel fee | On-time63% |