$187+ Cheap flights from the Dominican Republic 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Dominican Republic 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
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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 Dominican Republic to Chicago
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Cheapest flights from Dominican Republic to ChicagoExplore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
This eDestinos deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:30 pm -
Nonstop5h 10m
Sun 11/84:20 am -
Nonstop4h 45m
Deal found 9/20![Arajet logo]()
$318
This Arajet deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:40 am -
1 stop10h 30m
Sun 1/34:20 am -
1 stop10h 25m
Deal found 9/18![Multiple Airlines logo]()
$354
This Arajet deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:40 am -
1 stop10h 30m
Fri 11/275:45 am -
1 stop8h 35m
Deal found 9/18![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/317:00 am -
Nonstop5h 10m
Sat 11/711:10 am -
Nonstop4h 45m
Deal found 9/16![Arajet logo]()
$357
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:55 pm -
Nonstop5h 15m
Fri 1/17:38 am -
Nonstop4h 37m
Deal found 9/18![United Airlines logo]()
$372
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:00 am -
Nonstop5h 10m
Sat 11/2811:10 am -
Nonstop4h 45m
Deal found 9/18![Arajet logo]()
$375
This Arajet deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:25 pm -
1 stop9h 15m
Sun 11/84:20 am -
1 stop10h 25m
Deal found 9/18![Multiple Airlines logo]()
$377
This Orbitz deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Sat 11/217:00 am -
Nonstop5h 10m
Sat 11/287:05 am -
1 stop14h 30m
Deal found 9/16![Multiple Airlines logo]()
$377
This Booking.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/77:00 am -
Nonstop5h 10m
Sat 11/1411:10 am -
Nonstop4h 45m
Deal found 9/17![Arajet logo]()
$381
This Travelocity deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Thu 11/197:30 pm -
Nonstop5h 10m
Wed 11/253:45 pm -
1 stop29h 50m
Deal found 9/16![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/317:00 am -
Nonstop5h 10m
Sat 11/76:30 am -
2 stops27h 06m
Deal found 9/16![Multiple Airlines logo]()
$391
This Orbitz deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Sat 11/147:00 am -
Nonstop5h 10m
Sat 11/215:58 pm -
2 stops51h 37m
Deal found 9/17![Multiple Airlines logo]()
$395
Best flights from Dominican Republic to ChicagoDiscover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Arajet deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:40 am -
1 stop10h 30m
Sun 1/34:20 am -
1 stop10h 25m
Deal found 9/19![Multiple Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
Nonstop5h 15m
Sat 10/318:42 am -
Nonstop4h 37m
Deal found 9/19![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/224:45 pm -
1 stop7h 37m
Mon 1/46:00 am -
1 stop8h 42m
Deal found 9/17![Delta logo]()
$451
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:12 pm -
1 stop17h 35m
Tue 10/275:05 am -
1 stop8h 07m
Deal found 9/20![American Airlines logo]()
$510
This Copa Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/21:59 pm -
1 stop12h 09m
Tue 3/92:13 pm -
1 stop24h 59m
Deal found 9/20![Copa Airlines logo]()
$514
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:40 pm -
2 stops21h 00m
Mon 11/95:05 am -
1 stop8h 05m
Deal found 9/20![Southwest logo]()
$521
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:57 pm -
1 stop8h 33m
Mon 10/267:00 am -
1 stop6h 34m
Deal found 9/18![JetBlue logo]()
$550
This Arajet deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:40 am -
1 stop10h 30m
Sat 11/1411:10 am -
1 stop8h 30m
Deal found 9/19![Multiple Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:10 pm -
1 stop8h 49m
Mon 2/19:17 am -
Nonstop4h 40m
Deal found 9/19![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:06 pm -
1 stop7h 53m
Tue 1/56:00 am -
1 stop8h 20m
Deal found 9/18![Delta logo]()
$451
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:10 pm -
1 stop8h 49m
Fri 1/299:17 am -
Nonstop4h 40m
Deal found 9/20![United Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/186:06 pm -
1 stop7h 44m
Tue 2/236:00 am -
1 stop8h 20m
Deal found 9/16![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/252:55 pm -
Nonstop5h 15m
Mon 2/19:17 am -
Nonstop4h 40m
Deal found 9/18![United Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/186:06 pm -
1 stop7h 44m
Mon 2/227:00 pm -
2 stops19h 20m
Deal found 9/16![Delta logo]()
$452
This Copa Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:10 pm -
1 stop14h 01m
Wed 11/182:13 pm -
1 stop19h 32m
Deal found 9/20![Copa Airlines logo]()
$547
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:01 am -
1 stop9h 49m
Thu 10/152:55 pm -
1 stop10h 09m
Deal found 9/18![JetBlue logo]()
$565
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1412:56 pm -
1 stop13h 03m
Sat 1/308:42 am -
Nonstop4h 37m
Deal found 9/19![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/182:30 pm -
1 stop10h 25m
Mon 2/225:10 am -
1 stop8h 25m
Deal found 9/16![Southwest logo]()
$597
This Copa Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:10 pm -
1 stop14h 01m
Wed 11/252:13 pm -
1 stop19h 32m
Deal found 9/16![Copa Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:10 pm -
2 stops18h 49m
Tue 11/106:00 am -
1 stop11h 59m
Deal found 9/19![Delta logo]()
$471
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:12 pm -
1 stop9h 21m
Tue 10/137:00 am -
1 stop6h 12m
Deal found 9/18![American Airlines logo]()
$628
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/183:57 pm -
1 stop8h 33m
Wed 10/217:00 am -
1 stop6h 47m
Deal found 9/20![JetBlue logo]()
$574
This Copa Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:10 pm -
1 stop14h 01m
Sat 11/212:13 pm -
1 stop9h 55m
Deal found 9/16![Copa Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 2/32:30 pm -
2 stops10h 30m
Sun 2/77:20 pm -
2 stops18h 15m
Deal found 9/17![Southwest logo]()
$654
This Copa Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:55 am -
1 stop17h 16m
Mon 11/92:13 pm -
1 stop19h 32m
Deal found 9/16![Copa Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:49 pm -
1 stop7h 33m
Fri 1/16:00 am -
1 stop8h 49m
Deal found 9/19![Delta logo]()
$498
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/112:55 pm -
Nonstop5h 15m
Mon 1/259:17 am -
Nonstop4h 40m
Deal found 9/19![United Airlines logo]()
$555
This Copa Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/298:52 am -
1 stop17h 15m
Fri 2/52:13 pm -
1 stop20h 53m
Deal found 9/18![Copa Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:50 pm -
2 stops17h 50m
Mon 11/303:40 pm -
2 stops20h 05m
Deal found 9/20![Southwest logo]()
$703
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:57 pm -
2 stops17h 44m
Sun 11/85:27 am -
1 stop7h 05m
Deal found 9/20![Delta logo]()
$557
Last-minute flights from Dominican Republic to ChicagoDiscover last-minute flight deals from Dominican Republic to Chicago. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Dominican Republic to Chicago. Data last updated September 21, 2026 and is based on user searches.
This Arajet deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:45 pm -
1 stop10h 55m
Sat 10/312:12 pm -
1 stop8h 28m
Deal found 9/20![Multiple Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:12 pm -
1 stop17h 35m
Tue 10/275:05 am -
1 stop8h 07m
Deal found 9/20![American Airlines logo]()
$510
This Trip.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:05 pm -
1 stop28h 07m
Wed 10/283:45 pm -
1 stop20h 00m
Deal found 9/20![Air Canada logo]()
$418
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Wed 10/2110:19 am -
2 stops14h 24m
Wed 10/286:42 pm -
2 stops27h 30m
Deal found 9/16![Multiple Airlines logo]()
$456
This Trip.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:05 pm -
1 stop28h 07m
Thu 10/297:05 am -
1 stop28h 40m
Deal found 9/19![Air Canada logo]()
$429
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:30 pm -
2 stops17h 01m
Sat 10/318:00 am -
2 stops34h 18m
Deal found 9/20![Multiple Airlines logo]()
$484
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Tue 10/273:35 pm -
2 stops27h 12m
Tue 11/36:42 pm -
2 stops19h 47m
Deal found 9/16![Multiple Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/297:30 pm -
Nonstop5h 10m
Thu 11/57:50 pm -
2 stops22h 24m
Deal found 9/16![Multiple Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
Nonstop5h 15m
Sat 10/318:42 am -
Nonstop4h 37m
Deal found 9/20![United Airlines logo]()
$414
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/295:02 pm -
2 stops25h 45m
Thu 11/56:16 am -
2 stops14h 56m
Deal found 9/16![Multiple Airlines logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/317:00 am -
Nonstop5h 10m
Sat 11/711:10 am -
Nonstop4h 45m
Deal found 9/16![Arajet logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/317:00 am -
Nonstop5h 10m
Sat 11/76:30 am -
2 stops27h 06m
Deal found 9/16![Multiple Airlines logo]()
$391
One-way flights from Dominican Republic to ChicagoSearch for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Arajet logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:00 am -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Arajet logo]()
$188
This Arajet deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:40 am -
1 stop10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$196
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Thu 1/147:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Arajet logo]()
$199
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Wed 1/205:39 pm -
Nonstop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/101:27 pm -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$202
This JetBlue deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/182:50 pm -
1 stop10h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![JetBlue logo]()
$205
This Super.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Arajet logo]()
$208
This Priceline deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/167:30 pm -
1 stop28h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$213
This Arajet deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:55 pm -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/183:50 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$221
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:44 pm -
1 stop8h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$222
Find flight deals from Dominican Republic to Chicago
Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (eDestinos) |
One-way from | $187 (Kiwi.com) |
Popular in | June |
Cheapest in | December |
Average price | $408 |
Good round-trip deal | $289 or less |
Good one-way deal | $312 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Dominican Republic 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 21, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 11/20
1:40 am-10:10 am
1 stop10h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$196
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Sun 10/4
1:55 pm-10:10 pm
1 stop9h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$219
Quickest round-trip
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 11/20
2:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$224
Santiago de los CaballerosChicago
STI Santiago de los Caballeros - ORD Chicago O'Hare Intl
STIORD
Santiago de los Caballeros
Fri 11/13
12:55 pm-5:20 pm
1 stop30h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$241
Santiago de los CaballerosChicago
STI Santiago de los Caballeros - ORD Chicago O'Hare Intl
STIORD
Santiago de los Caballeros
Fri 11/6
6:00 am-12:01 am
1 stop20h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$241
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 12/25
2:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$243
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
$243
Santiago de los CaballerosChicago
STI Santiago de los Caballeros - ORD Chicago O'Hare Intl
STIORD
Santiago de los Caballeros
Tue 11/10
5:08 pm-11:56 pm
1 stop8h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$245
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 11/21
2:39 pm-11:38 pm
1 stop10h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$246
Santiago de los CaballerosChicago
STI Santiago de los Caballeros - ORD Chicago O'Hare Intl
STIORD
Santiago de los Caballeros
Tue 11/10
7:00 am-7:05 pm
2 stops14h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Dominican Republic to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
PUJ-ORD
SDQ-ORD
STI-ORD
PUJ-MDW
SDQ-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 the Dominican Republic to Chicago
DO0-CHI
PUJ-ORD
SDQ-ORD
STI-ORD
PUJ-MDW
What is the cheapest month to book a flight from Dominican Republic to Chicago?
Currently, February is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $375). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $801). 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 DO to CHI?
Find hourly flight availability from Dominican Republic 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 21, 2026.
It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 59% on the cost of your flight, compared to a flight at noon.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 21, 2026.
Peruse reviews from past customers who have flown with American Airlines from the Dominican Republic to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Crew
7.9
Boarding
7.4
Overall
7.0
Comfort
7.2
Entertainment
6.8
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Related info for your journey
Find useful and relevant information for your journey from Dominican Republic 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
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Alternative routes for Dominican Republic 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 21, 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 Dominican Republic to Chicago by cabin class
Find flights from Dominican Republic to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Dominican Republic and Chicago flights
Browse other Dominican Republic and Chicago flight options. Last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Dominican Republic to Chicago
Discover the top 3 airlines that operate flights from Dominican Republic 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$237 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$656 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$375 | Average$411 | FlexibilityNo cancel fee | On-time62% |