$212+ Cheap flights from Punta Cana (PUJ) to Chicago (CHI)
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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Oct 6 — Oct 131
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Punta Cana to Chicago 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.Cheap flight deals from Punta Cana to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Punta Cana to ChicagoExplore the most affordable flight options available from Punta Cana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
Explore the most affordable flight options available from Punta Cana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 6, 2026.
This Expedia deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:30 pm -
Nonstop5h 10m
Sun 11/153:20 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$286
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:47 am -
Nonstop5h 10m
Sat 11/2810:27 am -
Nonstop4h 45m
Deal found 9/2![Arajet logo]()
$310
This Booking.com deal was found by Cheapflights users on 9/1. 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 10/247:02 am -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$313
This Booking.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 am -
Nonstop5h 10m
Fri 11/65:45 am -
Nonstop4h 45m
Deal found 9/5![Arajet logo]()
$321
This Booking.com deal was found by Cheapflights users on 9/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:47 am -
Nonstop5h 10m
Sat 11/1410:27 am -
Nonstop4h 45m
Deal found 9/4![Arajet logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Sat 9/197:02 am -
Nonstop5h 10m
Sat 9/2612:12 pm -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$361
This Booking.com deal was found by Cheapflights users on 9/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 am -
Nonstop5h 10m
Sat 11/710:27 am -
Nonstop4h 45m
Deal found 9/4![Arajet logo]()
$363
This Booking.com deal was found by Cheapflights users on 9/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
Nonstop5h 10m
Sat 10/1712:12 pm -
Nonstop4h 45m
Deal found 9/2![Arajet logo]()
$364
This Arajet deal was found by Cheapflights users on 9/1. 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.
Thu 10/297:30 pm -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$366
This Expedia deal was found by Cheapflights users on 9/4. 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 11/215:47 am -
Nonstop5h 10m
Sat 11/282:00 pm -
2 stops21h 45m
Deal found 9/4![Multiple Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/243:40 pm -
1 stop8h 42m
Fri 1/16:00 am -
1 stop8h 41m
Deal found 9/2![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 9/1. 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.
Sat 12/194:45 pm -
1 stop7h 37m
Mon 1/46:00 am -
1 stop8h 42m
Deal found 9/1![Delta logo]()
$510
Best flights from Punta Cana to ChicagoDiscover carefully curated flight deals from Punta Cana to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Punta Cana to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This Arajet deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/5![Arajet logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
Nonstop5h 15m
Thu 11/59:41 pm -
1 stop13h 27m
Deal found 9/5![United Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/243:40 pm -
1 stop8h 42m
Fri 1/16:00 am -
1 stop8h 41m
Deal found 9/2![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 9/1. 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.
Thu 11/54:50 pm -
1 stop8h 05m
Sun 11/85:05 am -
1 stop6h 40m
Deal found 9/1![Southwest logo]()
$536
This Arajet deal was found by Cheapflights users on 9/1. 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.
Sat 12/195:47 am -
Nonstop5h 10m
Sun 1/33:20 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:25 pm -
Nonstop5h 16m
Mon 1/49:17 am -
Nonstop4h 40m
Deal found 9/5![United Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 9/1. 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.
Sat 12/194:45 pm -
1 stop9h 14m
Mon 1/45:30 am -
1 stop8h 00m
Deal found 9/1![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/316:06 pm -
1 stop7h 44m
Sun 2/77:10 am -
1 stop7h 32m
Deal found 9/5![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Thu 10/291:55 pm -
Nonstop5h 15m
Sat 10/315:30 am -
1 stop8h 34m
Deal found 9/3![United Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/243:40 pm -
1 stop9h 23m
Fri 1/16:25 am -
1 stop7h 55m
Deal found 9/2![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 12/247:30 pm -
1 stop18h 20m
Sat 1/27:38 am -
Nonstop4h 37m
Deal found 9/4![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 1/216:06 pm -
2 stops16h 39m
Sat 1/306:00 am -
1 stop7h 30m
Deal found 9/2![Delta logo]()
$428
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/115:10 pm -
1 stop8h 49m
Mon 1/259:17 am -
Nonstop4h 40m
Deal found 9/5![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:45 pm -
2 stops18h 40m
Tue 10/275:45 am -
1 stop7h 00m
Deal found 9/5![Southwest logo]()
$607
This Delta deal was found by Cheapflights users on 9/2. 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 1/226:06 pm -
2 stops16h 39m
Sat 1/306:00 am -
1 stop7h 30m
Deal found 9/2![Delta logo]()
$428
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 1/1412:56 pm -
1 stop13h 03m
Mon 2/18:40 am -
1 stop6h 48m
Deal found 9/4![United Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 1/216:06 pm -
1 stop16h 28m
Fri 1/297:10 am -
1 stop7h 32m
Deal found 9/2![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:10 pm -
2 stops18h 10m
Tue 1/55:20 am -
1 stop7h 20m
Deal found 9/5![Southwest logo]()
$628
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:10 pm -
2 stops18h 10m
Mon 1/45:05 am -
1 stop8h 05m
Deal found 9/5![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 9/1. 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.
Sat 12/194:45 pm -
1 stop7h 37m
Mon 1/46:00 am -
1 stop8h 42m
Deal found 9/1![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 9/3. 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.
Thu 12/243:40 pm -
1 stop8h 42m
Sat 1/26:00 am -
1 stop8h 41m
Deal found 9/3![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/222:05 pm -
1 stop10h 17m
Mon 1/46:00 am -
1 stop7h 30m
Deal found 9/5![Delta logo]()
$586
Last-minute flights from Punta Cana to ChicagoDiscover last-minute flight deals from Punta Cana to Chicago. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Punta Cana to Chicago. Data last updated September 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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 9/64:04 pm -
2 stops18h 13m
Mon 10/261:27 pm -
2 stops22h 13m
Deal found 9/3![Delta logo]()
$588
This Kiwi.com deal was found by Cheapflights users on 9/1. 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.
Sat 9/197:02 am -
Nonstop5h 10m
Sat 9/2612:12 pm -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$361
This eDestinos deal was found by Cheapflights users on 9/1. 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 9/267:02 am -
Nonstop5h 10m
Sat 10/312:12 pm -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$380
This Booking.com deal was found by Cheapflights users on 9/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
Nonstop5h 10m
Sat 10/1712:12 pm -
Nonstop4h 45m
Deal found 9/2![Arajet logo]()
$364
This Booking.com deal was found by Cheapflights users on 9/1. 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 10/177:02 am -
Nonstop5h 10m
Sat 10/2412:12 pm -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$370
This Trip.com deal was found by Cheapflights users on 9/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:05 pm -
1 stop28h 07m
Mon 10/264:30 am -
Nonstop4h 45m
Deal found 9/3![Multiple Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:45 pm -
2 stops18h 40m
Tue 10/275:45 am -
1 stop7h 00m
Deal found 9/5![Southwest logo]()
$607
This Trip.com deal was found by Cheapflights users on 9/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:05 pm -
1 stop28h 07m
Fri 10/306:45 am -
Nonstop4h 45m
Deal found 9/3![Multiple Airlines logo]()
$381
This Booking.com deal was found by Cheapflights users on 9/1. 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 10/247:02 am -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$313
This Arajet deal was found by Cheapflights users on 9/1. 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.
Thu 10/297:30 pm -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$366
This Booking.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 am -
Nonstop5h 10m
Fri 11/65:45 am -
Nonstop4h 45m
Deal found 9/5![Arajet logo]()
$321
This Booking.com deal was found by Cheapflights users on 9/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:47 am -
Nonstop5h 10m
Sat 11/710:27 am -
Nonstop4h 45m
Deal found 9/4![Arajet logo]()
$363
One-way flights from Punta Cana to ChicagoSearch for one-way flight options from Punta Cana to Chicago. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Punta Cana to Chicago. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:39 pm -
Nonstop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$212
This Mytrip deal was found by Cheapflights users on 9/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:02 am -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Arajet logo]()
$213
This Booking.com deal was found by Cheapflights users on 9/1. 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.
Thu 12/177:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Arajet logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Arajet logo]()
$215
This Mytrip deal was found by Cheapflights users on 9/3. 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.
Sat 1/305:47 am -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Arajet logo]()
$216
This Super.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/47:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Arajet logo]()
$221
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:33 pm -
1 stop15h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/221:59 pm -
2 stops26h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$224
This Orbitz deal was found by Cheapflights users on 9/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:30 pm -
1 stop29h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$225
This Booking.com deal was found by Cheapflights users on 9/3. 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.
Thu 9/177:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Arajet logo]()
$229
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Wed 11/42:55 pm -
Nonstop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:05 pm -
2 stops21h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$235
Find flight deals from Punta Cana to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Punta Cana (PUJ) to Chicago (CHI). 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 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $266 (eDestinos) |
One-way from | $212 (American Airlines) |
Popular in | June |
Cheapest in | December |
Average price | $511 |
Good round-trip deal | $496 or less |
Good one-way deal | $312 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Punta Cana to Chicago 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 6, 2026.
Use the filters below to find and compare flights from Punta Cana to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Wed 11/4
2:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Wed 12/2
4:55 pm-1:01 pm
2 stops22h 06m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$235
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Tue 10/6
3:35 pm-11:32 pm
1 stop8h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$235
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Wed 11/11
7:30 pm-12:01 am
1 stop30h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$235
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 11/12
12:56 pm-7:30 am
1 stop20h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$235
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Fri 10/2
2:08 pm-10:36 am
2 stops21h 28m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$236
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Thu 12/3
2:40 pm-10:55 pm
1 stop10h 15m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$236
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Thu 10/29
4:05 pm-10:33 pm
1 stop7h 28m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$236
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Fri 12/4
4:55 pm-10:55 pm
1 stop8h 00m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$236
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Wed 12/2
12:56 pm-5:00 pm
1 stop30h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$236
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Punta Cana to Chicago
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 Punta Cana to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Punta Cana-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Punta Cana-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Punta Cana-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Punta Cana-Chicago 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 Punta Cana-Chicago 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 Punta Cana to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Punta Cana with our price prediction graph.
PUJ-CHI
PUJ-ORD
PUJ-MDW
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 Punta Cana to Chicago
PUJ-CHI
PUJ-ORD
PUJ-MDW
What is the cheapest month to book a flight from Punta Cana to Chicago?
Currently, December is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $286). Flying from Punta Cana to Chicago in March is currently the most expensive (average of $821). 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 PUJ to CHI?
Find hourly flight availability from Punta Cana to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 6, 2026.
It’s typically best to fly out from Punta Cana to Chicago in the evening. Doing so could potentially save you 63% on the flight price compared to flying at noon, which is usually more expensive.
The best insider tips for Punta Cana to Chicago 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 Punta Cana to Chicago trip
Our travel experts
Related info for your journey
Find useful and relevant information for your journey from Punta Cana to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Punta Cana
Popular flights
Alternative routes for Punta Cana to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 6, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Punta Cana to Chicago by cabin class
Find flights from Punta Cana to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Punta Cana and Chicago flights
Browse other Punta Cana and Chicago flight options. Last updated on September 6, 2026.
Other flights from Punta Cana
Browse through other flights departing from Punta Cana. Flights are based on user searches made on Cheapflights and were last updated on September 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Punta Cana to Chicago
Discover the top 2 airlines that operate flights from Punta Cana to Chicago. 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$237 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$650 | FlexibilityNo cancel fee | On-time71% |