$155+ Cheap flights from Chicago (CHI) to the Dominican Republic
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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Dominican Republic 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 Chicago to Dominican Republic
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Cheapest flights from Chicago to Dominican RepublicExplore the most affordable flight options available from Chicago to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Chicago to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:24 pm -
1 stop17h 46m
Sun 12/131:27 pm -
1 stop8h 57m
Deal found 11/3![Frontier logo]()
$359
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$380
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop7h 58m
Tue 11/107:00 am -
1 stop14h 49m
Deal found 11/2![American Airlines logo]()
$380
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:53 pm -
1 stop7h 13m
Tue 11/244:28 pm -
1 stop8h 50m
Deal found 11/1![Frontier logo]()
$381
This JetBlue deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:00 am -
1 stop7h 18m
Thu 12/32:37 pm -
1 stop10h 56m
Deal found 10/30![JetBlue logo]()
$382
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$385
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/57:00 am -
Nonstop5h 10m
Deal found 10/30![Arajet logo]()
$388
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:50 pm -
1 stop18h 08m
Tue 11/107:00 am -
1 stop13h 23m
Deal found 11/2![American Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:57 am -
2 stops10h 56m
Wed 11/113:55 pm -
1 stop8h 12m
Deal found 10/30![American Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:55 am -
2 stops27h 16m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 11/2![Multiple Airlines logo]()
$392
This Expedia deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/197:15 pm -
1 stop8h 18m
Deal found 10/30![Multiple Airlines logo]()
$394
Best flights from Chicago to Dominican RepublicDiscover carefully curated flight deals from Chicago to Dominican Republic that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Chicago to Dominican Republic that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:45 pm -
1 stop16h 58m
Thu 1/286:15 pm -
1 stop7h 40m
Deal found 10/31![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/188:59 pm -
2 stops14h 57m
Thu 1/282:36 pm -
1 stop9h 18m
Deal found 11/3![American Airlines logo]()
$425
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:00 am -
1 stop6h 58m
Tue 12/222:50 pm -
1 stop10h 43m
Deal found 11/3![JetBlue logo]()
$439
This Copa Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/132:13 pm -
1 stop9h 51m
Mon 2/2212:42 pm -
1 stop26h 04m
Deal found 11/1![Copa Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:05 am -
1 stop6h 40m
Thu 12/174:50 pm -
1 stop8h 10m
Deal found 11/1![Southwest logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/810:45 am -
1 stop7h 50m
Wed 1/136:42 pm -
2 stops23h 09m
Deal found 11/2![Multiple Airlines logo]()
$654
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
1 stop6h 58m
Fri 12/44:55 pm -
2 stops25h 22m
Deal found 10/30![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:59 pm -
1 stop17h 57m
Thu 1/212:36 pm -
2 stops18h 23m
Deal found 11/3![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/87:30 pm -
1 stop14h 15m
Deal found 11/2![United Airlines logo]()
$426
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:00 am -
1 stop6h 48m
Tue 1/125:20 pm -
1 stop8h 27m
Deal found 11/2![JetBlue logo]()
$461
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:55 pm -
2 stops20h 33m
Tue 11/174:55 pm -
1 stop8h 59m
Deal found 10/30![Delta logo]()
$445
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/79:17 am -
Nonstop4h 40m
Tue 1/1212:56 pm -
1 stop12h 48m
Deal found 11/2![United Airlines logo]()
$466
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/47:00 am -
1 stop7h 18m
Sat 1/93:00 pm -
1 stop10h 47m
Deal found 11/2![JetBlue logo]()
$474
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:27 pm -
2 stops21h 01m
Wed 11/183:53 pm -
2 stops19h 53m
Deal found 10/30![Delta logo]()
$445
This Copa Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:17 pm -
1 stop19h 25m
Mon 12/77:03 pm -
1 stop19h 43m
Deal found 10/31![Copa Airlines logo]()
$546
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:50 am -
1 stop6h 38m
Sat 11/1412:56 pm -
1 stop7h 59m
Deal found 11/2![United Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:00 am -
1 stop7h 19m
Fri 1/292:44 pm -
1 stop11h 03m
Deal found 10/31![JetBlue logo]()
$491
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/307:10 am -
1 stop7h 40m
Tue 2/24:58 pm -
1 stop7h 22m
Deal found 11/2![Delta logo]()
$480
This Copa Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/117:35 am -
1 stop27h 31m
Sun 2/215:53 am -
1 stop20h 18m
Deal found 11/3![Copa Airlines logo]()
$598
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:46 pm -
1 stop8h 10m
Mon 12/76:01 am -
1 stop9h 29m
Deal found 11/1![JetBlue logo]()
$510
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/105:25 am -
1 stop7h 05m
Fri 1/154:35 pm -
1 stop8h 25m
Deal found 11/3![Southwest logo]()
$683
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:28 am -
1 stop9h 07m
Sun 11/1511:35 am -
1 stop24h 13m
Deal found 11/3![Multiple Airlines logo]()
$686
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/256:00 am -
1 stop7h 33m
Tue 2/24:58 pm -
1 stop8h 57m
Deal found 10/31![Delta logo]()
$480
This Copa Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/122:13 pm -
1 stop19h 07m
Sun 1/1712:35 pm -
1 stop13h 32m
Deal found 11/3![Copa Airlines logo]()
$628
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:00 am -
1 stop7h 18m
Thu 11/262:39 pm -
1 stop10h 59m
Deal found 11/1![JetBlue logo]()
$522
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop8h 48m
Wed 1/134:55 pm -
1 stop7h 22m
Deal found 11/3![Delta logo]()
$480
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:17 am -
1 stop7h 18m
Mon 12/287:15 pm -
2 stops15h 10m
Deal found 11/2![Multiple Airlines logo]()
$721
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:55 am -
1 stop9h 51m
Sun 12/202:50 am -
1 stop10h 25m
Deal found 11/1![United Airlines logo]()
$615
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/125:00 am -
1 stop6h 56m
Sun 1/172:36 pm -
2 stops18h 51m
Deal found 10/31![American Airlines logo]()
$747
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated November 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop7h 58m
Tue 11/107:00 am -
1 stop14h 49m
Deal found 11/2![American Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:57 am -
2 stops10h 56m
Wed 11/113:55 pm -
1 stop8h 12m
Deal found 10/30![American Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:50 pm -
1 stop18h 08m
Tue 11/107:00 am -
1 stop13h 23m
Deal found 11/2![American Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:55 am -
2 stops27h 16m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 11/2![Multiple Airlines logo]()
$392
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:53 pm -
1 stop7h 13m
Tue 11/244:28 pm -
1 stop8h 50m
Deal found 11/1![Frontier logo]()
$381
This JetBlue deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:00 am -
1 stop7h 18m
Fri 12/42:37 pm -
1 stop10h 56m
Deal found 10/30![JetBlue logo]()
$382
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$380
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/57:00 am -
Nonstop5h 10m
Deal found 10/30![Arajet logo]()
$388
This Expedia deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:10 am -
Nonstop4h 45m
Sat 12/197:15 pm -
1 stop8h 18m
Deal found 10/30![Multiple Airlines logo]()
$394
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 11/1![JetBlue logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:24 pm -
1 stop17h 46m
Sun 12/131:27 pm -
1 stop8h 57m
Deal found 11/3![Frontier logo]()
$359
One-way flights from Chicago to Dominican RepublicSearch for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:50 pm -
1 stop17h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![American Airlines logo]()
$155
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:00 pm -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![JetBlue logo]()
$169
This Arajet deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/34:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Arajet logo]()
$174
This FlightHub deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/135:16 pm -
1 stop18h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/128:25 am -
2 stops25h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$177
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/287:00 am -
1 stop7h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![JetBlue logo]()
$178
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:38 am -
Nonstop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/57:00 am -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![JetBlue logo]()
$182
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:00 pm -
1 stop16h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![American Airlines logo]()
$183
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/56:00 am -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$183
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/36:00 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$183
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$184
Find flight deals from Chicago to Dominican Republic
Keep the following information in mind while searching for Chicago to Dominican Republic flight deals. Data was last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $356 (Priceline) |
One-way from | $155 (American Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $591 |
Good round-trip deal | $446 or less |
Good one-way deal | $283 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Dominican Republic that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Thu 11/12
7:50 pm-2:55 pm
1 stop17h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$155
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Thu 11/12
1:00 pm-3:05 am
1 stop12h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$169
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 1/2
7:00 am-4:22 pm
1 stop7h 22m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$178
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 1/5
7:00 am-3:48 pm
1 stop6h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$179
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 12/1
5:55 am-5:28 pm
1 stop9h 33m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sun 1/17
6:00 am-4:55 pm
1 stop8h 55m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 1/4
5:05 am-1:45 pm
1 stop6h 40m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoLa Romana
ORD Chicago O'Hare Intl - LRM La Romana
ORDLRM
Chicago O'Hare Intl
Thu 12/31
8:00 pm-2:28 pm
1 stop16h 28m
La Romana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 11/22
8:40 pm-11:45 am
1 stop13h 05m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 1/11
6:00 am-4:48 pm
1 stop8h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Dominican Republic
Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Chicago with our price prediction graph.
ORD-SDQ
ORD-PUJ
ORD-LRM
MDW-PUJ
RFD-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Dominican Republic
CHI-DO0
ORD-SDQ
ORD-PUJ
ORD-LRM
MDW-PUJ
What is the cheapest month to book a flight from Chicago to Dominican Republic?
Currently, January is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $455). Flying from Chicago to Dominican Republic in June is currently the most expensive (average of $685). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to DO?
Find hourly flight availability from Chicago to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
When flying from Chicago to Dominican Republic, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Dominican Republic
Explore weekly flight availability from Chicago to Dominican Republic. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2026.
The most flights from CHI to DO0 are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How often are flights from Chicago to the Dominican Republic delayed?
About 22% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 145 minutes.
What is the most punctual flight time for Chicago to the Dominican Republic flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to the Dominican Republic flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago to Dominican Republic?
The price you pay for your flight from Chicago to Dominican Republic may vary depending on when you book. For the best chance of a lower fare, look to book 17 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Dominican Republic
Get insights into the airlines that provide service to Dominican Republic. 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 Dominican Republic. Reviews last updated November 4, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to the Dominican Republic 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.
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Dominican Republic. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Dominican Republic
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Dominican Republic by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Dominican Republic by cabin class
Find flights from Chicago to Dominican Republic, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Dominican Republic flights
Browse other Chicago and Dominican Republic flight options. Last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Dominican Republic regions
Consider these flights traveling to Dominican Republic regions.
Top 9 airlines flying from Chicago to Dominican Republic
Discover the top 9 airlines that operate flights from Chicago to Dominican Republic. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$454 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$510 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$246 | Average$771 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$255 | Average$479 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$633 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$401 | Average$672 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$511 | Average$726 | FlexibilityNo cancel fee | On-time63% |