$118+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Sep 4 — Sep 111
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 June, booked 11 days in advance, depart on a Tuesday or Friday and return on a Thursday
Cheap flight deals from Chicago to Cabo San Lucas
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Cheapest flights from Chicago to Cabo San LucasExplore the most affordable flight options available from Chicago to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 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 August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Thu 9/247:47 pm -
1 stop8h 05m
Deal found 7/31![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 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 9/91:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$351
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 Justfly.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.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
Mon 8/317:47 pm -
1 stop8h 05m
Deal found 7/31![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 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.
Tue 8/252:53 am -
1 stop10h 36m
Sun 9/67:47 pm -
1 stop8h 05m
Deal found 8/2![Volaris logo]()
$357
This FlightHub 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 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 8/1![Volaris logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Mon 11/97:27 am -
1 stop8h 20m
Deal found 7/31![Multiple Airlines logo]()
$526
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 August 5, 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 August 5, 2026.
This Viva 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:40 pm -
1 stop19h 03m
Wed 10/287:54 pm -
1 stop13h 06m
Deal found 8/3![Viva logo]()
$354
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 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 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 1/246:00 am -
2 stops12h 51m
Wed 1/271:30 pm -
1 stop7h 40m
Deal found 8/2![Delta logo]()
$607
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 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:55 am -
2 stops9h 20m
Wed 11/411:50 am -
2 stops8h 40m
Deal found 7/31![Southwest logo]()
$612
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 10/227:35 am -
1 stop13h 29m
Mon 10/263:38 pm -
1 stop12h 05m
Deal found 8/4![Volaris logo]()
$473
This Volaris deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 7/31![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 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 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.
Fri 9/117:20 am -
2 stops28h 51m
Mon 9/144:34 pm -
1 stop17h 33m
Deal found 8/1![Alaska Airlines logo]()
$618
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 United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Wed 11/412:55 pm -
Nonstop4h 16m
Deal found 7/31![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.
Fri 10/307:20 am -
1 stop11h 18m
Fri 11/611:48 am -
2 stops16h 52m
Deal found 8/2![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.
Sat 11/147:35 am -
1 stop7h 45m
Tue 11/172:05 pm -
1 stop9h 05m
Deal found 8/4![Southwest logo]()
$650
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.
Sun 8/92:53 am -
1 stop7h 23m
Fri 8/1412:43 pm -
1 stop9h 23m
Deal found 8/3![Volaris logo]()
$631
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:52 am -
Nonstop4h 33m
Mon 10/2611:55 am -
Nonstop4h 13m
Deal found 8/4![United Airlines logo]()
$636
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:00 am -
1 stop7h 25m
Thu 12/31:25 pm -
1 stop8h 31m
Deal found 8/4![Delta logo]()
$715
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:30 am -
1 stop9h 00m
Sat 10/1011:20 am -
2 stops16h 20m
Deal found 7/31![Southwest logo]()
$655
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:45 am -
1 stop7h 35m
Fri 10/911:05 am -
1 stop8h 45m
Deal found 7/31![Southwest logo]()
$678
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:55 am -
1 stop8h 45m
Sat 10/319:40 am -
1 stop7h 05m
Deal found 8/1![Southwest logo]()
$687
Last-minute flights from Chicago to Cabo San LucasDiscover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cabo San Lucas. Data last updated August 5, 2026 and is based on user searches.
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 Justfly.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.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
Mon 8/317:47 pm -
1 stop8h 05m
Deal found 7/31![Volaris logo]()
$354
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.
Tue 8/252:53 am -
1 stop10h 36m
Sun 9/67:47 pm -
1 stop8h 05m
Deal found 8/2![Volaris logo]()
$357
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 8/3. 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.
Sun 9/61:40 am -
1 stop10h 29m
Sat 9/123:36 pm -
1 stop7h 19m
Deal found 8/3![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.
Mon 9/71:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$349
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 8/5. 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 9/91:40 am -
1 stop10h 29m
Sun 9/137:47 pm -
1 stop8h 05m
Deal found 8/5![Volaris logo]()
$351
This FlightHub 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 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 8/1![Volaris logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Thu 9/247:47 pm -
1 stop8h 05m
Deal found 7/31![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.
Sat 9/197:35 am -
1 stop13h 29m
Sat 10/37:47 pm -
1 stop8h 05m
Deal found 8/3![Volaris logo]()
$356
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
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 August 5, 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 August 5, 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 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:40 pm -
1 stop18h 51m
Deal found 7/31![Viva logo]()
$120
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 am -
1 stop13h 29m
Deal found 8/3![Volaris logo]()
$130
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.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 7/31![Volaris logo]()
$135
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 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 8/137:35 am -
1 stop13h 29m
Deal found 8/5![Volaris logo]()
$138
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 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am -
1 stop13h 29m
Deal found 7/31![Volaris logo]()
$141
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:53 am -
1 stop10h 36m
Deal found 7/31![Volaris logo]()
$142
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 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 Cabo San Lucas
Keep the following information in mind while searching for Chicago to Cabo San Lucas flight deals. Data was last updated August 5, 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 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 August 5, 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 10/24
2:40 pm-7:43 am
1 stop19h 03m
San José del Cabo Los Cabos
Wed 10/28
7:54 pm-11:00 am
1 stop13h 06m
$354
ChicagoSan José del Cabo
ORD - SJD
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 - SJD
ORDSJD
Chicago O'Hare Intl
Thu 10/22
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 10/26
3:38 pm-5:43 am
1 stop12h 05m
$473
ChicagoSan José del Cabo
ORD - SJD
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 - SJD
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
ChicagoSan José del Cabo
ORD - SJD
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
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 11/1
9:03 am-1:03 pm
Nonstop5h 00m
San José del Cabo Los Cabos
Wed 11/4
12:55 pm-6:11 pm
Nonstop4h 16m
$593
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 1/24
6:00 am-5:51 pm
2 stops12h 51m
San José del Cabo Los Cabos
Wed 1/27
1:30 pm-10:10 pm
1 stop7h 40m
$607
ChicagoSan José del Cabo
ORD - SJD
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 - SJD
MDWSJD
Chicago Midway
Sun 11/1
5:55 am-2:15 pm
2 stops9h 20m
San José del Cabo Los Cabos
Wed 11/4
11:50 am-9:30 pm
2 stops8h 40m
$612
Showing 1-10 of 39 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 August 5, 2026.
When flying from Chicago to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago to Cabo San Lucas?
Airfare is below average for this route at the moment.
Chicago to Cabo San Lucas flights typically cost between $472 and $713 in September.The cheapest round-trip price found within the last 5 days was $347 on Volaris (Sep 19-Sep 24).
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 August 5, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to Cabo San Lucas to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Comfort
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 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
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Chicago and Cabo San Lucas flights
Browse other Chicago and Cabo San Lucas flight options. Last updated on August 5, 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 August 5, 2026.
Popular flight searches
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Chicago to Cabo San Lucas flights
Consider these flights traveling from Chicago to Cabo San Lucas.
Top 4 airlines flying from Chicago to Cabo San Lucas
Discover the top 4 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 August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$390 | 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% |