$222+ Cheap flights from Punta Cana (PUJ) to Chicago (CHI)
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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 August 24, 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 August 24, 2026.
This Expedia deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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 8/23![Arajet logo]()
$346
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 8/24![Arajet logo]()
$348
This Booking.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/21![Arajet logo]()
$350
This Arajet deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/20![Arajet logo]()
$354
This Booking.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.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 8/21![Arajet logo]()
$368
This Booking.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/23![Arajet logo]()
$370
This FlightHub deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 pm -
Nonstop5h 10m
Mon 9/285:30 am -
Nonstop4h 45m
Deal found 8/21![Arajet logo]()
$374
This Travelocity deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:02 am -
Nonstop5h 10m
Sat 10/172:00 pm -
2 stops25h 05m
Deal found 8/20![Multiple Airlines logo]()
$378
This Trip.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:15 pm -
1 stop25h 37m
Sun 11/13:20 am -
Nonstop4h 45m
Deal found 8/23![Multiple Airlines logo]()
$390
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:05 pm -
1 stop9h 00m
Mon 11/95:05 am -
1 stop8h 05m
Deal found 8/22![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:45 pm -
1 stop7h 25m
Sat 1/26:00 am -
1 stop8h 41m
Deal found 8/19![Delta logo]()
$510
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:25 pm -
1 stop7h 20m
Sat 10/315:55 am -
1 stop6h 05m
Deal found 8/23![Southwest logo]()
$558
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 August 24, 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 August 24, 2026.
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1412:56 pm -
1 stop24h 17m
Mon 2/19:30 am -
Nonstop4h 32m
Deal found 8/23![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:06 pm -
1 stop7h 44m
Fri 2/55:30 am -
1 stop9h 12m
Deal found 8/22![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:40 pm -
2 stops10h 00m
Mon 11/95:05 am -
1 stop8h 05m
Deal found 8/22![Southwest logo]()
$498
This Mytrip deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:35 pm -
2 stops16h 25m
Sun 10/1111:45 am -
2 stops22h 55m
Deal found 8/21![Multiple Airlines logo]()
$756
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:39 am -
2 stops24h 11m
Fri 9/411:50 am -
1 stop25h 37m
Deal found 8/20![Frontier logo]()
$794
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:06 pm -
1 stop7h 44m
Sun 1/317:10 am -
1 stop6h 20m
Deal found 8/23![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
1 stop25h 06m
Thu 12/317:38 am -
Nonstop4h 37m
Deal found 8/23![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:06 pm -
1 stop7h 44m
Fri 1/17:05 am -
1 stop6h 25m
Deal found 8/20![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:56 pm -
1 stop13h 05m
Mon 11/99:41 pm -
1 stop17h 47m
Deal found 8/22![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:06 pm -
1 stop7h 44m
Fri 1/295:30 am -
1 stop9h 12m
Deal found 8/22![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:35 pm -
1 stop16h 50m
Mon 9/289:52 pm -
1 stop13h 48m
Deal found 8/21![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:25 pm -
1 stop7h 20m
Sat 10/315:55 am -
1 stop6h 05m
Deal found 8/23![Southwest logo]()
$558
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:45 pm -
1 stop8h 54m
Sat 1/26:25 am -
1 stop7h 55m
Deal found 8/22![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:45 pm -
2 stops18h 40m
Sat 10/315:55 am -
1 stop6h 05m
Deal found 8/19![Southwest logo]()
$626
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:35 pm -
1 stop7h 25m
Mon 9/287:55 pm -
2 stops16h 25m
Deal found 8/23![Southwest logo]()
$738
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:45 pm -
1 stop8h 15m
Sun 10/185:10 am -
1 stop7h 40m
Deal found 8/20![Southwest logo]()
$789
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:25 pm -
2 stops11h 30m
Sun 11/18:40 pm -
2 stops16h 30m
Deal found 8/19![Southwest logo]()
$807
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:50 pm -
1 stop8h 54m
Mon 9/286:05 am -
1 stop6h 20m
Deal found 8/23![Delta logo]()
$840
Last-minute flights from Punta Cana to ChicagoDiscover last-minute flight deals from Punta Cana to Chicago. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Punta Cana to Chicago. Data last updated August 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:29 pm -
1 stop10h 58m
Tue 9/112:44 am -
1 stop15h 21m
Deal found 8/22![Multiple Airlines logo]()
$417
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:37 pm -
1 stop8h 10m
Sat 9/56:05 am -
1 stop7h 22m
Deal found 8/21![Frontier logo]()
$612
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:01 pm -
2 stops10h 46m
Thu 9/103:20 pm -
1 stop18h 40m
Deal found 8/19![Multiple Airlines logo]()
$644
This Trip.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:15 pm -
1 stop9h 12m
Fri 9/116:45 am -
Nonstop4h 45m
Deal found 8/21![Multiple Airlines logo]()
$412
This Booking.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:02 am -
Nonstop5h 10m
Sat 9/1212:12 pm -
Nonstop4h 45m
Deal found 8/20![Arajet logo]()
$413
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/127:02 am -
Nonstop5h 10m
Sat 9/1912:12 pm -
Nonstop4h 45m
Deal found 8/24![Arajet logo]()
$391
This Booking.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/197:02 am -
Nonstop5h 10m
Sat 9/2612:12 pm -
Nonstop4h 45m
Deal found 8/24![Arajet logo]()
$348
This Mytrip deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:02 am -
Nonstop5h 10m
Sat 9/263:40 pm -
1 stop23h 25m
Deal found 8/22![Multiple Airlines logo]()
$414
This FlightHub deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 pm -
Nonstop5h 10m
Mon 9/285:30 am -
Nonstop4h 45m
Deal found 8/21![Arajet logo]()
$374
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/247:30 pm -
Nonstop5h 10m
Thu 10/18:45 am -
1 stop30h 20m
Deal found 8/24![Multiple Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:35 pm -
1 stop7h 25m
Mon 9/287:55 pm -
2 stops16h 25m
Deal found 8/23![Southwest logo]()
$738
This Booking.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:02 am -
Nonstop5h 10m
Sat 10/312:12 pm -
Nonstop4h 45m
Deal found 8/20![Arajet logo]()
$401
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 August 24, 2026.
Search for one-way flight options from Punta Cana to Chicago. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:18 pm -
1 stop8h 34m
Deal found 8/21![American Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:29 pm -
1 stop27h 58m
Deal found 8/23![Frontier logo]()
$223
This Booking.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:02 am -
Nonstop5h 10m
Deal found 8/21![Arajet logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:29 pm -
1 stop27h 58m
Deal found 8/21![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 pm -
Nonstop5h 10m
Deal found 8/22![Arajet logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:30 pm -
Nonstop5h 10m
Deal found 8/22![Arajet logo]()
$227
This Faresmojo deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:06 pm -
1 stop7h 44m
Deal found 8/21![JetBlue logo]()
$228
This Trip.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:40 pm -
1 stop23h 18m
Deal found 8/20![Air Canada logo]()
$229
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:10 pm -
Nonstop5h 05m
Deal found 8/22![Southwest logo]()
$230
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:55 pm -
Nonstop5h 15m
Deal found 8/20![United Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:49 pm -
1 stop19h 27m
Deal found 8/23![Multiple Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:34 pm -
Nonstop5h 34m
Deal found 8/19![American Airlines logo]()
$233
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 August 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $346 (Expedia) |
One-way from | $222 (American Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $425 |
Good round-trip deal | $490 or less |
Good one-way deal | $273 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 August 24, 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
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 1/14
12:56 pm-11:13 am
1 stop24h 17m
Chicago O'Hare Intl
Mon 2/1
9:30 am-4:02 pm
Nonstop4h 32m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 1/29
6:06 pm-11:50 pm
1 stop7h 44m
Chicago O'Hare Intl
Fri 2/5
5:30 am-4:42 pm
1 stop9h 12m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 1/14
6:06 pm-11:50 pm
1 stop7h 44m
Chicago O'Hare Intl
Sun 1/31
7:10 am-3:30 pm
1 stop6h 20m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 12/24
7:30 pm-6:36 pm
1 stop25h 06m
Chicago O'Hare Intl
Thu 12/31
7:38 am-2:15 pm
Nonstop4h 37m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 12/24
6:06 pm-11:50 pm
1 stop7h 44m
Chicago O'Hare Intl
Fri 1/1
7:05 am-3:30 pm
1 stop6h 25m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 1/14
6:06 pm-11:50 pm
1 stop7h 44m
Chicago O'Hare Intl
Fri 1/29
5:30 am-4:42 pm
1 stop9h 12m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 12/24
2:45 pm-9:39 pm
1 stop8h 54m
Chicago O'Hare Intl
Sat 1/2
6:25 am-4:20 pm
1 stop7h 55m
$427
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 11/6
12:56 pm-12:01 am
1 stop13h 05m
Chicago O'Hare Intl
Mon 11/9
9:41 pm-5:28 pm
1 stop17h 47m
$428
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 9/24
3:35 pm-7:25 am
1 stop16h 50m
Chicago O'Hare Intl
Mon 9/28
9:52 pm-12:40 pm
1 stop13h 48m
$446
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Fri 11/6
2:40 pm-10:40 pm
2 stops10h 00m
Chicago Midway
Mon 11/9
5:05 am-3:10 pm
1 stop8h 05m
$498
Showing 1-10 of 34 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 August.
| 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, October is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $358). 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 August 24, 2026.
It’s typically best to fly out from Punta Cana to Chicago in the evening. Doing so could potentially save you 61% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Punta Cana to Chicago
Explore weekly flight availability from Punta Cana to Chicago. 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 24, 2026.
The most flights from PUJ to CHI are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Punta Cana to Chicago?
Airfare is below average for this route at the moment.
Punta Cana to Chicago flights typically cost between $461 and $506 in October.The cheapest round-trip price found within the last 5 days was $346 on Arajet (Oct 31-Nov 7).
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
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Porter
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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 August 24, 2026.
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Punta Cana and Chicago flights
Browse other Punta Cana and Chicago flight options. Last updated on August 24, 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 August 24, 2026.
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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 August 24, 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% |