$242+ Cheap flights from Chicago (CHI) to Barbados
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BGI
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Barbados 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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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 Barbados
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Cheapest flights from Chicago to BarbadosExplore the most affordable flight options available from Chicago to Barbados. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2026.
Explore the most affordable flight options available from Chicago to Barbados. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 1, 2026.
This Justfly.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:45 am -
1 stop27h 40m
Thu 11/54:50 pm -
1 stop24h 02m
Deal found 9/28![Air Canada logo]()
$531
This Trip.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:05 am -
1 stop29h 35m
Sun 12/63:45 pm -
1 stop21h 22m
Deal found 9/26![Air Canada logo]()
$534
This Trip.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:45 am -
1 stop27h 40m
Fri 10/303:00 pm -
1 stop27h 43m
Deal found 9/28![Air Canada logo]()
$543
This Travelocity deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:55 pm -
2 stops47h 50m
Mon 11/234:00 pm -
1 stop27h 43m
Deal found 9/29![Air Canada logo]()
$555
This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:40 pm -
2 stops17h 05m
Sun 11/14:00 pm -
1 stop19h 23m
Deal found 9/29![Air Canada logo]()
$563
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:05 am -
1 stop30h 40m
Wed 12/24:05 pm -
1 stop19h 03m
Deal found 9/28![Air Canada logo]()
$565
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:55 pm -
2 stops22h 30m
Fri 10/303:00 pm -
2 stops21h 07m
Deal found 9/28![Air Canada logo]()
$566
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
1 stop7h 20m
Thu 12/314:30 pm -
1 stop18h 43m
Deal found 9/29![Delta logo]()
$886
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop7h 20m
Tue 12/14:29 pm -
2 stops27h 32m
Deal found 9/29![Delta logo]()
$892
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
3 stops30h 10m
Fri 10/303:00 pm -
3 stops27h 47m
Deal found 9/29![Multiple Airlines logo]()
$940
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:44 pm -
2 stops18h 36m
Tue 12/14:29 pm -
2 stops22h 32m
Deal found 9/29![Delta logo]()
$977
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
3 stops41h 43m
Fri 11/134:00 pm -
2 stops33h 47m
Deal found 9/29![Multiple Airlines logo]()
$979
Best flights from Chicago to BarbadosDiscover carefully curated flight deals from Chicago to Barbados that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
Discover carefully curated flight deals from Chicago to Barbados that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
This Justfly.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:45 am -
1 stop27h 40m
Thu 11/54:50 pm -
2 stops25h 02m
Deal found 9/26![Air Canada logo]()
$539
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/35:30 am -
1 stop7h 50m
Wed 2/244:30 pm -
1 stop18h 04m
Deal found 9/27![Delta logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:15 am -
1 stop13h 44m
Wed 11/256:00 am -
2 stops13h 29m
Deal found 9/30![American Airlines logo]()
$660
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
3 stops30h 10m
Fri 10/303:00 pm -
3 stops27h 47m
Deal found 9/29![Multiple Airlines logo]()
$940
This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
1 stop26h 10m
Sun 11/14:50 pm -
1 stop24h 10m
Deal found 9/29![Air Canada logo]()
$565
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 3/245:30 am -
1 stop7h 50m
Wed 3/313:30 pm -
1 stop18h 04m
Deal found 9/26![Delta logo]()
$650
This Air Canada deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:30 pm -
1 stop19h 55m
Tue 11/174:00 pm -
2 stops21h 07m
Deal found 9/26![Air Canada logo]()
$613
This Air Canada deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:15 pm -
1 stop24h 10m
Wed 10/214:20 pm -
1 stop24h 31m
Deal found 9/27![Air Canada logo]()
$620
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 3/295:30 am -
1 stop7h 50m
Mon 4/53:30 pm -
1 stop9h 20m
Deal found 9/26![Delta logo]()
$690
This Justfly.com deal was found by Cheapflights users on 10/1. 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.
Tue 10/278:45 am -
1 stop27h 40m
Fri 10/303:00 pm -
1 stop25h 38m
Deal found 10/1![Air Canada logo]()
$620
This Air Canada deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:55 pm -
1 stop22h 45m
Sat 12/124:05 pm -
1 stop19h 03m
Deal found 9/30![Air Canada logo]()
$655
This Mytrip deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:16 am -
3 stops30h 09m
Tue 11/174:00 pm -
3 stops33h 47m
Deal found 9/26![Multiple Airlines logo]()
$1,061
This Air Canada deal was found by Cheapflights users on 10/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:21 pm -
1 stop15h 04m
Sun 11/224:50 pm -
1 stop24h 10m
Deal found 10/1![Air Canada logo]()
$660
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:00 am -
1 stop7h 20m
Thu 12/314:30 pm -
1 stop18h 43m
Deal found 9/27![Delta logo]()
$886
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:40 pm -
3 stops27h 15m
Fri 10/235:15 am -
3 stops19h 28m
Deal found 9/29![Multiple Airlines logo]()
$1,078
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop7h 20m
Tue 12/14:29 pm -
2 stops27h 32m
Deal found 9/27![Delta logo]()
$892
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:44 pm -
2 stops18h 36m
Tue 12/14:29 pm -
2 stops22h 32m
Deal found 9/29![Delta logo]()
$977
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/136:00 am -
1 stop7h 20m
Wed 3/173:30 pm -
2 stops22h 03m
Deal found 9/27![Delta logo]()
$986
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/146:00 am -
1 stop7h 20m
Wed 3/173:30 pm -
2 stops22h 03m
Deal found 9/27![Delta logo]()
$1,041
Last-minute flights from Chicago to BarbadosDiscover last-minute flight deals from Chicago to Barbados. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Barbados. Data last updated October 1, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/246:21 am -
3 stops30h 04m
Sat 10/313:00 pm -
3 stops34h 47m
Deal found 9/26![Multiple Airlines logo]()
$1,012
This Air Canada deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:40 pm -
2 stops17h 05m
Sun 11/14:00 pm -
1 stop19h 23m
Deal found 9/29![Air Canada logo]()
$563
This Trip.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:45 am -
1 stop27h 40m
Fri 10/303:00 pm -
1 stop27h 43m
Deal found 9/28![Air Canada logo]()
$543
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
3 stops30h 10m
Fri 10/303:00 pm -
3 stops27h 47m
Deal found 9/29![Multiple Airlines logo]()
$940
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:55 pm -
2 stops22h 30m
Fri 10/303:00 pm -
2 stops21h 07m
Deal found 9/28![Air Canada logo]()
$566
This Justfly.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:45 am -
1 stop27h 40m
Thu 11/54:50 pm -
1 stop24h 02m
Deal found 9/28![Air Canada logo]()
$531
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
3 stops41h 43m
Fri 11/134:00 pm -
2 stops33h 47m
Deal found 9/29![Multiple Airlines logo]()
$979
This Travelocity deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:55 pm -
2 stops47h 50m
Mon 11/234:00 pm -
1 stop27h 43m
Deal found 9/29![Air Canada logo]()
$555
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:45 am -
1 stop27h 40m
Tue 12/14:00 pm -
1 stop19h 08m
Deal found 9/28![Air Canada logo]()
$570
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop7h 20m
Tue 12/14:29 pm -
2 stops27h 32m
Deal found 9/29![Delta logo]()
$892
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:44 pm -
2 stops18h 36m
Tue 12/14:29 pm -
2 stops22h 32m
Deal found 9/29![Delta logo]()
$977
This Air Canada deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:55 pm -
2 stops23h 50m
Wed 12/24:05 pm -
1 stop23h 08m
Deal found 9/28![Air Canada logo]()
$565
One-way flights from Chicago to BarbadosSearch for one-way flight options from Chicago to Barbados. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
Search for one-way flight options from Chicago to Barbados. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This Trip.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:05 am -
1 stop30h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$242
This Orbitz deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 am -
1 stop29h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$256
This Trip.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/18:45 am -
1 stop27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Air Canada logo]()
$276
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:56 pm -
2 stops18h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$296
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:30 pm -
1 stop19h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:42 pm -
3 stops43h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/16:00 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:42 pm -
3 stops42h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$318
This Expedia deal was found by Cheapflights users on 10/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2010:05 am -
2 stops26h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$335
This Mytrip deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:16 am -
3 stops30h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:16 am -
3 stops53h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/11:18 pm -
3 stops47h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$466
Find flight deals from Chicago to Barbados
Keep the following information in mind while searching for Chicago to Barbados flight deals. Data was last updated October 1, 2026.
Round-trip from | $531 (Justfly.com) |
|---|---|
One-way from | $242 (Trip.com) |
Popular in | November |
Cheapest in | May |
Average price | $717 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Barbados 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 7,457,451 searches. Data last updated October 1, 2026.
Use the filters below to find and compare flights from Chicago to Barbados that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Thu 10/29
7:03 am-1:25 pm
1 stop29h 22m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$256
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Mon 3/1
3:45 pm-2:25 pm
2 stops20h 40m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$283
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Mon 12/28
5:56 pm-2:40 pm
2 stops18h 44m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$296
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Mon 11/2
4:30 pm-2:25 pm
1 stop19h 55m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$301
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Thu 10/29
4:42 pm-1:26 pm
3 stops43h 44m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$311
Quickest round-trip
ChicagoBridgetown
MDW Chicago Midway - BGI Bridgetown Grantley Adams Intl
MDWBGI
Chicago Midway
Mon 3/1
6:00 am-3:20 pm
1 stop7h 20m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Sun 12/20
10:05 am-2:40 pm
2 stops26h 35m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$335
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Fri 11/27
11:00 am-3:45 pm
3 stops26h 45m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$370
ChicagoBridgetown
MDW Chicago Midway - BGI Bridgetown Grantley Adams Intl
MDWBGI
Chicago Midway
Mon 11/2
6:16 am-1:21 pm
3 stops53h 05m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$401
ChicagoBridgetown
ORD Chicago O'Hare Intl - BGI Bridgetown Grantley Adams Intl
ORDBGI
Chicago O'Hare Intl
Mon 3/1
5:32 pm-3:00 pm
3 stops43h 28m
Bridgetown Grantley Adams Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$439
Showing 1-10 of 34 resultsSorted by cheapest first
Best time to book a flight from Chicago to Barbados
Have a flexible travel schedule? Discover the best time to fly to Barbados from Chicago with our price prediction graph.
ORD-BGI
MDW-BGI
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 Barbados
CHI-BB0
ORD-BGI
MDW-BGI
What is the cheapest month to book a flight from Chicago to Barbados?
Currently, May is the cheapest month in which you can book a flight from Chicago to Barbados (average of $640). Flying from Chicago to Barbados in November is currently the most expensive (average of $1,125). 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.
Reviews of airlines servicing Barbados
Get insights into the airlines that provide service to Barbados. 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 Barbados. Reviews last updated October 1, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAir Canada from Chicago to Barbados to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Barbados. 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 Barbados
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Complete your trip
Complete your trip to Barbados by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Barbados by cabin class
Find flights from Chicago to Barbados, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Barbados flights
Browse other Chicago and Barbados flight options. Last updated on October 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Barbados
Discover the top 3 airlines that operate flights from Chicago to Barbados. 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 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$524 | Average$916 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$529 | Average$670 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$539 | Average$719 | FlexibilityNo cancel fee | On-time71% |