$174+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Dec 4 — Dec 111
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 17 days in advance, depart on a Monday or Saturday and return on a Sunday
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 November 4, 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 November 4, 2026.
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$380
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:53 pm -
1 stop7h 13m
Tue 11/244:28 pm -
1 stop8h 50m
Deal found 11/1![Frontier logo]()
$381
This JetBlue deal was found by Cheapflights users on 10/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:00 am -
1 stop7h 18m
Thu 12/32:37 pm -
1 stop10h 56m
Deal found 10/30![JetBlue logo]()
$382
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$385
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/57:00 am -
Nonstop5h 10m
Deal found 10/30![Arajet logo]()
$388
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 11/147:55 am -
2 stops27h 16m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 11/2![Multiple Airlines logo]()
$392
This Expedia deal was found by Cheapflights users on 10/30. 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.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/197:15 pm -
1 stop8h 18m
Deal found 10/30![Multiple Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:14 am -
Nonstop4h 54m
Sat 12/54:24 pm -
1 stop18h 41m
Deal found 11/1![American Airlines logo]()
$396
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.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 11/1![Arajet logo]()
$398
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop6h 28m
Thu 12/32:40 pm -
1 stop10h 14m
Deal found 11/1![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop6h 28m
Fri 12/44:55 pm -
2 stops18h 42m
Deal found 10/30![Delta logo]()
$405
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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:45 pm -
1 stop16h 58m
Thu 1/286:15 pm -
1 stop7h 40m
Deal found 10/31![Delta logo]()
$400
This JetBlue deal was found by Cheapflights users on 11/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:00 am -
1 stop6h 58m
Tue 12/222:50 pm -
1 stop10h 43m
Deal found 11/3![JetBlue logo]()
$439
This Southwest deal was found by Cheapflights users on 11/1. 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.
Sun 12/135:05 am -
1 stop6h 40m
Thu 12/174:50 pm -
1 stop8h 10m
Deal found 11/1![Southwest logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/810:45 am -
1 stop7h 50m
Wed 1/136:42 pm -
2 stops23h 09m
Deal found 11/2![Multiple Airlines logo]()
$654
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
1 stop6h 58m
Fri 12/44:55 pm -
2 stops25h 22m
Deal found 10/30![Delta logo]()
$405
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/87:30 pm -
1 stop14h 15m
Deal found 11/2![United Airlines logo]()
$426
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:00 am -
1 stop6h 48m
Tue 1/125:20 pm -
1 stop8h 27m
Deal found 11/2![JetBlue logo]()
$461
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:55 pm -
2 stops20h 33m
Tue 11/174:55 pm -
1 stop8h 59m
Deal found 10/30![Delta logo]()
$445
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 1/79:17 am -
Nonstop4h 40m
Tue 1/1212:56 pm -
1 stop12h 48m
Deal found 11/2![United Airlines logo]()
$466
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/47:00 am -
1 stop7h 18m
Sat 1/93:00 pm -
1 stop10h 47m
Deal found 11/2![JetBlue logo]()
$474
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:27 pm -
2 stops21h 01m
Wed 11/183:53 pm -
2 stops19h 53m
Deal found 10/30![Delta logo]()
$445
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/78:50 am -
1 stop6h 38m
Sat 11/1412:56 pm -
1 stop7h 59m
Deal found 11/2![United Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:00 am -
1 stop7h 18m
Thu 11/262:39 pm -
1 stop10h 59m
Deal found 11/1![JetBlue logo]()
$522
This Delta deal was found by Cheapflights users on 11/2. 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.
Sat 1/307:10 am -
1 stop7h 40m
Tue 2/24:58 pm -
1 stop7h 22m
Deal found 11/2![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/105:25 am -
1 stop7h 05m
Fri 1/154:35 pm -
1 stop8h 25m
Deal found 11/3![Southwest logo]()
$683
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 11/139:28 am -
1 stop9h 07m
Sun 11/1511:35 am -
1 stop24h 13m
Deal found 11/3![Multiple Airlines logo]()
$686
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/256:00 am -
1 stop7h 33m
Tue 2/24:58 pm -
1 stop8h 57m
Deal found 10/31![Delta logo]()
$480
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop8h 48m
Wed 1/134:55 pm -
1 stop7h 22m
Deal found 11/3![Delta logo]()
$480
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/1111:17 am -
1 stop7h 18m
Mon 12/287:15 pm -
2 stops15h 10m
Deal found 11/2![Multiple Airlines logo]()
$721
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:44 pm -
2 stops15h 44m
Wed 12/24:55 pm -
1 stop7h 59m
Deal found 10/30![Delta logo]()
$485
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Fri 1/111:00 am -
1 stop7h 35m
Thu 1/76:58 pm -
2 stops16h 57m
Deal found 10/30![Multiple Airlines logo]()
$778
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:19 pm -
2 stops19h 21m
Sat 11/143:45 pm -
1 stop19h 05m
Deal found 10/30![Delta logo]()
$505
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/216:45 pm -
1 stop13h 09m
Sun 1/106:58 pm -
2 stops16h 57m
Deal found 10/30![Multiple Airlines logo]()
$840
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 12/46:00 am -
1 stop6h 28m
Wed 12/92:40 pm -
1 stop10h 14m
Deal found 11/2![Delta logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/236:42 pm -
2 stops15h 51m
Tue 12/2910:54 am -
1 stop25h 00m
Deal found 11/3![Multiple Airlines logo]()
$931
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop6h 28m
Thu 12/172:40 pm -
1 stop10h 14m
Deal found 10/30![Delta logo]()
$608
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop7h 29m
Tue 12/84:55 pm -
1 stop7h 59m
Deal found 11/1![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop6h 28m
Wed 11/254:55 pm -
2 stops20h 30m
Deal found 11/1![Delta logo]()
$662
Last-minute flights from Chicago to Punta CanaDiscover last-minute flight deals from Chicago to Punta Cana. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Punta Cana. Data last updated November 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 11/147:55 am -
2 stops27h 16m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 11/2![Multiple Airlines logo]()
$392
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.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 11/1![Arajet logo]()
$398
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:53 pm -
1 stop7h 13m
Tue 11/244:28 pm -
1 stop8h 50m
Deal found 11/1![Frontier logo]()
$381
This JetBlue deal was found by Cheapflights users on 10/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:00 am -
1 stop7h 18m
Fri 12/42:37 pm -
1 stop10h 56m
Deal found 10/30![JetBlue logo]()
$382
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$380
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/57:00 am -
Nonstop5h 10m
Deal found 10/30![Arajet logo]()
$388
This Expedia deal was found by Cheapflights users on 10/30. 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.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/197:15 pm -
1 stop8h 18m
Deal found 10/30![Multiple Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:14 am -
Nonstop4h 54m
Sat 12/54:24 pm -
1 stop18h 41m
Deal found 11/1![American Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop6h 28m
Thu 12/32:40 pm -
1 stop10h 14m
Deal found 11/1![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop6h 28m
Wed 12/24:55 pm -
2 stops18h 42m
Deal found 10/30![Delta logo]()
$405
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
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 November 4, 2026.
Search for one-way flight options from Chicago to Punta Cana. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Arajet deal was found by Cheapflights users on 10/31. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/34:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Arajet logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 1/128:25 am -
2 stops25h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$177
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![JetBlue logo]()
$178
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:38 am -
Nonstop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 10/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:00 am -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 11/2. 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.
Tue 1/56:00 am -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$183
This United Airlines deal was found by Cheapflights users on 11/3. 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 1/36:00 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$183
This JetBlue deal was found by Cheapflights users on 11/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$184
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:49 pm -
1 stop17h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$193
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:45 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Arajet logo]()
$194
This Super.com deal was found by Cheapflights users on 10/31. 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.
Thu 11/2611:53 pm -
1 stop7h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$196
This JetBlue deal was found by Cheapflights users on 11/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
1 stop6h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$198
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $380 (JetBlue) |
One-way from | $174 (Arajet) |
Popular in | June |
Cheapest in | September |
Average price | $591 |
Good round-trip deal | $446 or less |
Good one-way deal | $283 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 November 4, 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 1/2
7:00 am-4:22 pm
1 stop7h 22m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$178
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 1/5
7:00 am-3:48 pm
1 stop6h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$179
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sun 1/17
6:00 am-4:55 pm
1 stop8h 55m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 1/4
5:05 am-1:45 pm
1 stop6h 40m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 12/1
5:55 am-5:28 pm
1 stop9h 33m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 1/11
6:00 am-4:48 pm
1 stop8h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 11/22
8:40 pm-11:45 am
1 stop13h 05m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Thu 12/31
6:00 am-4:49 pm
1 stop8h 49m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 1/12
7:00 am-3:48 pm
1 stop6h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 12/6
8:52 am-5:28 pm
1 stop6h 36m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
Showing 1-10 of 59 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 November.
| 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 Accuracy2 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 | |
| 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
MDW-PUJ
RFD-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
MDW-PUJ
RFD-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 $438). 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 November 4, 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.
Weekly flight availability from Chicago to Punta Cana
Explore weekly flight availability from Chicago to Punta Cana. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2026.
The most flights from CHI to PUJ are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
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 $448 and $817 in January.The cheapest round-trip price found within the last 5 days was $380 on JetBlue (Jan 26-Feb 2).
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 145 minutes.
What is the most punctual flight time for Chicago to Punta Cana flights?
Historically, flights departing at night 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 November 4, 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.
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 November 4, 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 November 4, 2026.
Top 9 airlines flying from Chicago to Punta Cana
Discover the top 9 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$294 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$510 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$246 | Average$771 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$401 | Average$737 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$425 | Average$616 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$511 | Average$726 | FlexibilityNo cancel fee | On-time63% |