$148+ Cheap flights from Chicago (CHI) to Punta Cana (PUJ)
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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Punta Cana 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 Punta Cana are usually found in September or January, booked 67 days in advance, depart on a Monday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Punta Cana
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Cheapest flights from Chicago to Punta CanaExplore the most affordable flight options available from Chicago to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Chicago to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:24 pm -
1 stop14h 47m
Tue 11/34:31 pm -
1 stop9h 26m
Deal found 9/22![JetBlue logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sat 11/145:54 pm -
1 stop16h 04m
Sat 11/215:21 pm -
1 stop16h 04m
Deal found 9/21![American Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/1411:10 am -
Nonstop4h 45m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 9/19![Arajet logo]()
$361
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:00 am -
1 stop6h 25m
Tue 11/34:31 pm -
1 stop9h 26m
Deal found 9/23![JetBlue logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sun 10/258:55 pm -
1 stop12h 44m
Sun 11/15:33 pm -
1 stop17h 34m
Deal found 9/21![American Airlines logo]()
$365
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:00 am -
1 stop6h 25m
Sun 11/13:00 pm -
1 stop10h 57m
Deal found 9/23![JetBlue logo]()
$369
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
1 stop6h 26m
Fri 11/202:39 pm -
1 stop10h 59m
Deal found 9/22![JetBlue logo]()
$370
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop6h 25m
Fri 11/62:50 pm -
1 stop10h 46m
Deal found 9/22![JetBlue logo]()
$375
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 12/121:55 pm -
1 stop26h 50m
Sat 12/197:00 am -
Nonstop5h 10m
Deal found 9/18![Multiple Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/176:00 am -
1 stop7h 30m
Wed 11/184:55 pm -
1 stop7h 59m
Deal found 9/20![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/289:30 am -
2 stops24h 58m
Thu 12/33:53 pm -
1 stop9h 01m
Deal found 9/20![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/265:00 am -
1 stop6h 25m
Mon 11/24:50 pm -
2 stops18h 10m
Deal found 9/22![Southwest logo]()
$440
Best flights from Chicago to Punta CanaDiscover carefully curated flight deals from Chicago to Punta Cana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Chicago to Punta Cana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/169:17 am -
Nonstop4h 40m
Fri 11/202:55 pm -
Nonstop5h 15m
Deal found 9/21![United Airlines logo]()
$365
This Arajet deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:20 am -
Nonstop4h 45m
Sat 11/77:00 am -
Nonstop5h 10m
Deal found 9/18![Arajet logo]()
$385
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/1411:18 am -
2 stops23h 10m
Thu 11/194:55 pm -
1 stop8h 59m
Deal found 9/19![Delta logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/308:44 am -
1 stop10h 41m
Tue 11/32:21 pm -
2 stops44h 19m
Deal found 9/22![Multiple Airlines logo]()
$509
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:25 pm -
2 stops17h 25m
Thu 11/124:50 pm -
1 stop8h 10m
Deal found 9/21![Southwest logo]()
$555
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Wed 10/286:04 am -
1 stop9h 24m
Wed 11/42:55 pm -
Nonstop5h 15m
Deal found 9/22![United Airlines logo]()
$420
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/256:00 am -
1 stop8h 04m
Sun 11/15:10 pm -
1 stop8h 51m
Deal found 9/19![United Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 26m
Tue 11/35:05 pm -
1 stop7h 28m
Deal found 9/21![Delta logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1910:39 am -
1 stop29h 01m
Tue 10/278:14 am -
2 stops49h 36m
Deal found 9/23![Multiple Airlines logo]()
$563
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/317:38 am -
Nonstop4h 37m
Sat 11/74:25 pm -
Nonstop5h 16m
Deal found 9/21![United Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/286:49 am -
1 stop6h 41m
Wed 12/94:55 pm -
2 stops23h 01m
Deal found 9/19![Delta logo]()
$560
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/298:45 pm -
2 stops16h 25m
Sun 12/64:05 pm -
1 stop9h 00m
Deal found 9/19![Southwest logo]()
$645
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/168:49 am -
1 stop10h 36m
Tue 10/209:25 am -
1 stop24h 19m
Deal found 9/20![Multiple Airlines logo]()
$643
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/306:04 am -
1 stop7h 36m
Tue 11/35:05 pm -
1 stop7h 28m
Deal found 9/22![Delta logo]()
$595
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/318:42 am -
Nonstop4h 37m
Tue 11/32:55 pm -
Nonstop5h 15m
Deal found 9/21![United Airlines logo]()
$546
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:55 pm -
2 stops15h 05m
Tue 11/32:40 pm -
2 stops10h 00m
Deal found 9/22![Southwest logo]()
$690
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/96:00 am -
1 stop7h 29m
Wed 12/164:55 pm -
1 stop7h 59m
Deal found 9/22![Delta logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1910:39 am -
1 stop29h 01m
Sun 10/2512:35 pm -
1 stop22h 19m
Deal found 9/23![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:20 am -
1 stop7h 20m
Fri 12/114:05 pm -
1 stop9h 00m
Deal found 9/22![Southwest logo]()
$700
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Fri 10/237:55 pm -
1 stop15h 20m
Mon 10/264:10 pm -
1 stop8h 52m
Deal found 9/21![United Airlines logo]()
$612
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/69:28 am -
1 stop8h 57m
Fri 11/132:21 pm -
2 stops45h 19m
Deal found 9/22![Multiple Airlines logo]()
$685
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:25 pm -
2 stops17h 25m
Tue 11/173:35 pm -
1 stop7h 55m
Deal found 9/20![Southwest logo]()
$725
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop6h 28m
Wed 12/94:55 pm -
1 stop7h 59m
Deal found 9/19![Delta logo]()
$660
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Thu 12/177:38 am -
Nonstop4h 37m
Tue 12/222:55 pm -
Nonstop5h 15m
Deal found 9/21![United Airlines logo]()
$616
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/238:44 am -
1 stop10h 41m
Tue 10/272:21 pm -
2 stops43h 29m
Deal found 9/18![Multiple Airlines logo]()
$709
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/269:17 am -
Nonstop4h 40m
Mon 11/22:55 pm -
Nonstop5h 15m
Deal found 9/22![United Airlines logo]()
$624
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/135:45 am -
1 stop7h 00m
Tue 10/202:45 pm -
2 stops18h 40m
Deal found 9/22![Southwest logo]()
$757
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/298:51 am -
1 stop7h 59m
Sun 12/611:35 am -
1 stop24h 52m
Deal found 9/22![Multiple Airlines logo]()
$759
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/17:38 am -
Nonstop4h 37m
Wed 11/42:55 pm -
Nonstop5h 15m
Deal found 9/22![United Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/105:20 am -
1 stop7h 20m
Tue 11/172:40 pm -
2 stops10h 05m
Deal found 9/22![Southwest logo]()
$819
Last-minute flights from Chicago to Punta CanaDiscover last-minute flight deals from Chicago to Punta Cana. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Punta Cana. Data last updated September 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Mon 9/286:29 am -
1 stop7h 43m
Mon 10/54:12 pm -
1 stop17h 48m
Deal found 9/21![American Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/246:25 am -
1 stop8h 05m
Sat 10/313:25 pm -
Nonstop5h 16m
Deal found 9/21![United Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sun 10/258:55 pm -
1 stop12h 44m
Sun 11/15:33 pm -
1 stop17h 34m
Deal found 9/21![American Airlines logo]()
$365
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:00 am -
1 stop6h 25m
Sun 11/13:00 pm -
1 stop10h 57m
Deal found 9/23![JetBlue logo]()
$369
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:00 am -
1 stop6h 25m
Tue 11/34:31 pm -
1 stop9h 26m
Deal found 9/23![JetBlue logo]()
$364
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:24 pm -
1 stop14h 47m
Mon 11/22:50 pm -
1 stop11h 07m
Deal found 9/22![JetBlue logo]()
$383
This Expedia deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/265:20 am -
Nonstop4h 45m
Sun 11/13:15 pm -
1 stop30h 37m
Deal found 9/22![Multiple Airlines logo]()
$393
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:24 pm -
1 stop14h 47m
Tue 11/34:31 pm -
1 stop9h 26m
Deal found 9/22![JetBlue logo]()
$359
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:24 pm -
1 stop14h 47m
Wed 11/42:50 pm -
1 stop11h 07m
Deal found 9/22![JetBlue logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Fri 10/309:29 pm -
1 stop16h 06m
Wed 11/44:51 pm -
1 stop9h 53m
Deal found 9/21![American Airlines logo]()
$360
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop6h 25m
Fri 11/62:50 pm -
1 stop10h 46m
Deal found 9/22![JetBlue logo]()
$375
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/317:38 am -
Nonstop4h 37m
Tue 11/1012:56 pm -
1 stop7h 58m
Deal found 9/21![United Airlines logo]()
$391
One-way flights from Chicago to Punta CanaSearch for one-way flight options from Chicago to Punta Cana. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Chicago to Punta Cana. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This CheapOair deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Sun 11/14:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Arajet logo]()
$148
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Fri 12/45:45 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Arajet logo]()
$154
This Booking.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 11/711:10 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Arajet logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/154:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Arajet logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/195:30 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Arajet logo]()
$157
This JetBlue deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![JetBlue logo]()
$158
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/317:38 am -
Nonstop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Mon 11/25:19 am -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/49:51 am -
2 stops29h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Multiple Airlines logo]()
$164
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sat 11/79:06 pm -
1 stop16h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$170
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/165:13 pm -
1 stop17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$198
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/159:30 am -
2 stops24h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$204
Find flight deals from Chicago to Punta Cana
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Punta Cana (PUJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (JetBlue) |
One-way from | $148 (CheapOair) |
Popular in | June |
Cheapest in | September |
Average price | $407 |
Good round-trip deal | $447 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Punta Cana 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 September 23, 2026.
Use the filters below to find and compare flights from Chicago to Punta Cana that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 10/31
7:00 am-2:25 pm
1 stop6h 25m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$158
Quickest round-trip
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 10/31
7:38 am-1:15 pm
Nonstop4h 37m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$159
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 10/30
8:24 pm-12:11 pm
1 stop14h 47m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$163
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 11/16
7:00 am-3:26 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$194
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/16
1:31 pm-12:28 pm
2 stops20h 57m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 11/17
5:30 am-3:30 pm
1 stop8h 00m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 11/14
2:44 pm-12:28 pm
2 stops19h 44m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 11/15
7:00 am-3:26 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 11/16
2:44 pm-12:28 pm
2 stops19h 44m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 10/20
7:00 am-2:27 pm
1 stop6h 27m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$217
Showing 1-10 of 55 resultsSorted by cheapest first
Compare providers for flights from Chicago to Punta Cana
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Punta Cana in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Punta Cana flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Punta Cana flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Punta Cana flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Punta Cana flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Punta Cana flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Punta Cana
Have a flexible travel schedule? Discover the best time to fly to Punta Cana from Chicago with our price prediction graph.
CHI-PUJ
ORD-PUJ
RFD-PUJ
MDW-PUJ
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 Punta Cana
CHI-PUJ
ORD-PUJ
RFD-PUJ
MDW-PUJ
What is the cheapest month to book a flight from Chicago to Punta Cana?
Currently, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $441). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $677). 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 PUJ?
Find hourly flight availability from Chicago to Punta Cana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Punta Cana as you normally would.
How much does it cost to fly round-trip from Chicago to Punta Cana?
Airfare is below average for this route at the moment.
Chicago to Punta Cana flights typically cost between $360 and $638 in October.The cheapest round-trip price found within the last 5 days was $359 on JetBlue (Oct 27-Nov 3).
What’s the top layover airport for flights from Chicago to Punta Cana?
Share of 1-stop round-trip flights from Chicago to Punta Cana chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 71% of 1-stop itineraries from Chicago to Punta Cana on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Punta Cana?
Average round-trip fare for 1-stop flights from Chicago to Punta Cana, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $440.
What’s the fastest layover option from Chicago to Punta Cana?
Shortest average travel time for 1-stop one-way flights from Chicago to Punta Cana, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Charlotte (CLT) have the shortest average one-way travel time for 1-stop routes: 6h 33m.
Which airport typically offers the quickest layover for flights from Chicago to Punta Cana?
Average layover duration for 1-stop one-way flights from Chicago to Punta Cana, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 05m.
How often are flights from Chicago to Punta Cana delayed?
About 22% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 146 minutes.
What is the most punctual flight time for Chicago to Punta Cana flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Punta Cana flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago to Punta Cana?
To ensure you get the cheapest price possible for a flight from Chicago to Punta Cana, you should look to book at least 17 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
The best insider tips for Chicago to Punta Cana flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Punta Cana trip
Our travel experts
Reviews of airlines servicing Punta Cana
Get insights into the airlines that provide service to Punta Cana. 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 Punta Cana. Reviews last updated September 23, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Punta Cana by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Punta Cana. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Punta Cana?
Book flights to Punta Cana if you plan to visit one of these locationsBavaro
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Chicago and Punta Cana flights
Browse other Chicago and Punta Cana flight options. Last updated on September 23, 2026.
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Explore flights to Punta Cana departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Top 8 airlines flying from Chicago to Punta Cana
Discover the top 8 airlines that operate flights from Chicago to Punta Cana. 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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$774 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$231 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$511 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$263 | Average$434 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$355 | Average$714 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$394 | Average$605 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$503 | Average$755 | FlexibilityNo cancel fee | On-time63% |