$163+ Cheap flights from Chicago (CHI) to Punta Cana (PUJ)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Sep 4 — Sep 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 Wednesday and return on a Friday
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 August 5, 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 August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm -
Nonstop4h 45m
Sat 9/197:02 am -
Nonstop5h 10m
Deal found 7/31![Arajet logo]()
$382
This Expedia deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm -
Nonstop4h 45m
Tue 10/272:15 pm -
1 stop21h 52m
Deal found 8/4![Multiple Airlines logo]()
$383
This Booking.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:57 am -
2 stops29h 48m
Sat 11/75:47 am -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$384
This Mytrip deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:40 pm -
1 stop23h 25m
Thu 9/247:30 pm -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$385
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:21 pm -
2 stops20h 44m
Thu 9/177:30 pm -
Nonstop5h 10m
Deal found 7/31![Multiple Airlines logo]()
$386
This Expedia deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 pm -
2 stops42h 25m
Sat 9/57:02 am -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$387
This Gotogate deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm -
Nonstop4h 45m
Mon 11/23:15 pm -
1 stop21h 52m
Deal found 8/1![Multiple Airlines logo]()
$388
This Travelocity deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:40 pm -
1 stop17h 45m
Sun 10/46:00 pm -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:53 pm -
1 stop17h 13m
Fri 9/44:14 pm -
1 stop8h 30m
Deal found 7/31![American Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop10h 00m
Deal found 8/4![Southwest logo]()
$390
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:12 pm -
Nonstop4h 45m
Sat 9/267:02 am -
Nonstop5h 10m
Deal found 8/1![Arajet logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:44 am -
1 stop17h 35m
Thu 9/177:30 pm -
Nonstop5h 10m
Deal found 8/1![Multiple Airlines logo]()
$392
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 August 5, 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 August 5, 2026.
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop8h 45m
Deal found 7/31![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:30 am -
1 stop7h 10m
Thu 11/53:55 pm -
1 stop9h 57m
Deal found 8/2![Delta logo]()
$390
This Arajet deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm -
Nonstop4h 45m
Sat 8/297:02 am -
Nonstop5h 10m
Deal found 8/4![Arajet logo]()
$455
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:41 pm -
1 stop13h 27m
Sat 11/212:55 pm -
Nonstop5h 15m
Deal found 8/3![United Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:30 pm -
2 stops20h 13m
Thu 9/174:00 pm -
2 stops16h 56m
Deal found 7/31![Delta logo]()
$395
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:30 pm -
2 stops16h 55m
Fri 9/182:08 pm -
2 stops23h 50m
Deal found 8/1![Delta logo]()
$395
This Arajet deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am -
Nonstop4h 45m
Sun 9/136:00 pm -
Nonstop5h 10m
Deal found 8/1![Arajet logo]()
$455
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:38 am -
Nonstop4h 37m
Sat 11/212:55 pm -
Nonstop5h 15m
Deal found 8/3![United Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:30 pm -
1 stop16h 29m
Thu 9/174:00 pm -
2 stops16h 56m
Deal found 7/31![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:55 pm -
2 stops16h 30m
Thu 9/171:45 pm -
1 stop10h 00m
Deal found 7/31![Southwest logo]()
$608
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop6h 05m
Tue 9/222:15 pm -
1 stop7h 35m
Deal found 8/1![Southwest logo]()
$609
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:30 am -
Nonstop4h 32m
Sat 12/124:25 pm -
Nonstop5h 13m
Deal found 8/4![United Airlines logo]()
$638
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
1 stop6h 25m
Sat 12/55:05 pm -
1 stop7h 51m
Deal found 8/4![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 pm -
2 stops16h 25m
Thu 9/241:45 pm -
2 stops18h 45m
Deal found 7/31![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:22 pm -
2 stops17h 03m
Mon 11/232:40 pm -
1 stop8h 08m
Deal found 8/3![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:22 pm -
2 stops17h 03m
Sun 11/222:40 pm -
1 stop8h 08m
Deal found 8/3![Delta logo]()
$538
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:55 pm -
2 stops16h 30m
Sun 10/42:50 pm -
1 stop9h 45m
Deal found 8/2![Southwest logo]()
$708
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:22 pm -
2 stops17h 03m
Wed 11/253:50 pm -
1 stop10h 09m
Deal found 7/31![Delta logo]()
$608
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:40 pm -
2 stops16h 30m
Mon 11/94:50 pm -
1 stop8h 05m
Deal found 8/4![Southwest logo]()
$761
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am -
1 stop7h 27m
Thu 9/174:00 pm -
1 stop7h 45m
Deal found 7/31![Delta logo]()
$648
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:00 am -
1 stop6h 25m
Thu 11/263:50 pm -
1 stop9h 06m
Deal found 7/31![Delta logo]()
$660
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:04 am -
1 stop6h 26m
Mon 11/95:05 pm -
1 stop7h 51m
Deal found 8/3![Delta logo]()
$678
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:00 am -
1 stop6h 25m
Sat 12/123:50 pm -
1 stop9h 06m
Deal found 8/4![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:00 am -
1 stop6h 25m
Sat 12/123:50 pm -
1 stop9h 06m
Deal found 8/4![Delta logo]()
$680
Last-minute flights from Chicago to Punta CanaDiscover last-minute flight deals from Chicago to Punta Cana. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Punta Cana. Data last updated August 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am -
1 stop8h 40m
Sat 9/197:02 am -
Nonstop5h 10m
Deal found 7/31![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:44 am -
1 stop17h 35m
Thu 9/177:30 pm -
Nonstop5h 10m
Deal found 8/1![Multiple Airlines logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm -
Nonstop4h 45m
Sat 9/197:02 am -
Nonstop5h 10m
Deal found 7/31![Arajet logo]()
$382
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:53 pm -
1 stop17h 13m
Fri 9/44:14 pm -
1 stop8h 30m
Deal found 7/31![American Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop10h 00m
Deal found 8/4![Southwest logo]()
$390
This Expedia deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:40 pm -
2 stops42h 25m
Sat 9/57:02 am -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$387
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:12 pm -
Nonstop4h 45m
Sat 9/267:02 am -
Nonstop5h 10m
Deal found 8/1![Arajet logo]()
$391
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:21 pm -
2 stops20h 44m
Thu 9/177:30 pm -
Nonstop5h 10m
Deal found 7/31![Multiple Airlines logo]()
$386
This Mytrip deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:40 pm -
1 stop23h 25m
Thu 9/247:30 pm -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$385
This Orbitz deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:35 pm -
1 stop20h 50m
Thu 9/247:30 pm -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$383
This Orbitz deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:00 pm -
2 stops49h 05m
Sat 10/37:02 am -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$384
This Travelocity deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:40 pm -
1 stop17h 45m
Sun 10/46:00 pm -
Nonstop5h 10m
Deal found 8/3![Multiple Airlines logo]()
$389
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 August 5, 2026.
Search for one-way flight options from Chicago to Punta Cana. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Deal found 7/31![American Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
1 stop17h 35m
Deal found 8/1![Frontier logo]()
$166
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:21 am -
Nonstop4h 44m
Deal found 7/31![American Airlines logo]()
$174
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:55 pm -
1 stop12h 44m
Deal found 7/31![American Airlines logo]()
$176
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:21 am -
Nonstop4h 44m
Deal found 8/1![American Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:30 pm -
2 stops19h 12m
Deal found 8/3![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:55 pm -
2 stops20h 50m
Deal found 8/3![Delta logo]()
$178
This eDestinos deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am -
Nonstop4h 45m
Deal found 8/1![Arajet logo]()
$180
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:05 am -
1 stop8h 01m
Deal found 8/2![American Airlines logo]()
$181
This American Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:00 pm -
1 stop18h 10m
Deal found 8/1![American Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:45 pm -
2 stops19h 54m
Deal found 8/4![Delta logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:25 am -
3 stops34h 06m
Deal found 8/4![Multiple Airlines logo]()
$216
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 August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $382 (Kiwi.com) |
One-way from | $163 (American Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $503 |
Good round-trip deal | $522 or less |
Good one-way deal | $217 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 2,558,603 searches. Data last updated August 5, 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
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 8/31
5:00 am-1:40 pm
1 stop7h 40m
Punta Cana
Thu 9/3
1:45 pm-9:30 pm
1 stop8h 45m
$390
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 10/30
6:30 am-2:40 pm
1 stop7h 10m
Punta Cana
Thu 11/5
3:55 pm-11:52 pm
1 stop9h 57m
$390
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 9/5
2:30 pm-11:43 am
2 stops20h 13m
Punta Cana
Thu 9/17
4:00 pm-7:56 am
2 stops16h 56m
$395
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 8/23
7:30 pm-1:25 pm
2 stops16h 55m
Punta Cana
Fri 9/18
2:08 pm-12:58 pm
2 stops23h 50m
$395
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 8/22
12:12 pm-5:57 pm
Nonstop4h 45m
Punta Cana
Sat 8/29
7:02 am-11:12 am
Nonstop5h 10m
$455
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 9/4
6:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Sun 9/13
6:00 pm-10:10 pm
Nonstop5h 10m
$455
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 9/4
7:30 pm-12:59 pm
1 stop16h 29m
Punta Cana
Thu 9/17
4:00 pm-7:56 am
2 stops16h 56m
$465
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 11/16
9:41 pm-1:08 pm
1 stop13h 27m
Punta Cana
Sat 11/21
2:55 pm-6:10 pm
Nonstop5h 15m
$500
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 11/15
7:38 am-2:15 pm
Nonstop4h 37m
Punta Cana
Sat 11/21
2:55 pm-6:10 pm
Nonstop5h 15m
$535
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 11/30
6:00 am-2:25 pm
1 stop6h 25m
Punta Cana
Sat 12/5
5:05 pm-10:56 pm
1 stop7h 51m
$535
Showing 1-10 of 42 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 August.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- 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
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
What is the cheapest month to book a flight from Chicago to Punta Cana?
Currently, September is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $418). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $676). 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 August 5, 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 August 5, 2026.
The most flights from CHI to PUJ are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, 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 $403 and $628 in August.The cheapest round-trip price found within the last 5 days was $382 on Arajet (Aug 22-Sep 19).
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 140 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 18% 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 16 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 August 5, 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.
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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
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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 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$218 | Average$369 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$223 | Average$756 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$517 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$245 | Average$247 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$263 | Average$434 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$349 | Average$688 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$385 | Average$592 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$503 | Average$816 | FlexibilityNo cancel fee | On-time63% |