$138+ Cheap flights from Chicago (CHI) to the Dominican Republic
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Jul 15 — Jul 221
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 June 15, 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 June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/2812:29 am
ORD
- SDQ
1 stop17h 49m
Multiple Airlines
Sat 9/53:30 pm
SDQ
- ORD
1 stop7h 56m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$330
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Tue 8/187:00 am
ORD
- SDQ
1 stop7h 21m
JetBlue
Sat 8/291:34 pm
SDQ
- ORD
1 stop11h 10m
JetBlue
Deal found 6/10![JetBlue logo]()
$357
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Fri 8/142:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Tue 8/184:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/10![JetBlue logo]()
$358
This SmartFares deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Sat 8/291:34 pm
SDQ
- ORD
1 stop11h 10m
JetBlue
Deal found 6/14![JetBlue logo]()
$363
This Arajet deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 10/301:40 am
SDQ
- ORD
1 stop9h 17m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:29 am
ORD
- SDQ
1 stop15h 00m
Multiple Airlines
Mon 8/3112:41 pm
SDQ
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$372
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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.
Thu 8/132:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 8/205:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/12![JetBlue logo]()
$373
This Arajet deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 10/91:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 10/317:00 am
ORD
- SDQ
1 stop7h 16m
JetBlue
Thu 11/126:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$378
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 10/215:00 am
ORD
- SDQ
1 stop7h 00m
American Airlines
Sat 10/315:20 pm
SDQ
- ORD
1 stop7h 22m
American Airlines
Deal found 6/11![American Airlines logo]()
$380
This FlightHub deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/207:00 am
ORD
- SDQ
1 stop7h 21m
JetBlue
Tue 8/255:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/14![JetBlue logo]()
$381
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:45 am
ORD
- SDQ
2 stops10h 59m
American Airlines
Tue 9/82:00 pm
SDQ
- ORD
1 stop9h 30m
American Airlines
Deal found 6/11![American Airlines logo]()
$385
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 June 15, 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 June 15, 2026.
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/286:00 am
ORD
- STI
1 stop6h 27m
JetBlue
Fri 10/23:49 pm
STI
- ORD
1 stop8h 42m
JetBlue
Deal found 6/10![JetBlue logo]()
$426
This Arajet deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/10![Arajet logo]()
$430
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:05 am
ORD
- STI
2 stops9h 41m
Delta
Tue 11/106:40 am
STI
- ORD
1 stop12h 54m
Delta
Deal found 6/15![Delta logo]()
$431
This Copa Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/43:21 pm
ORD
- SDQ
1 stop10h 04m
Copa Airlines
Sun 7/126:42 pm
SDQ
- ORD
1 stop20h 15m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/25:00 am
ORD
- PUJ
1 stop9h 30m
United Airlines
Thu 9/103:35 pm
PUJ
- ORD
1 stop17h 09m
United Airlines
Deal found 6/11![United Airlines logo]()
$540
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:59 am
ORD
- STI
1 stop13h 30m
American Airlines
Sun 8/97:00 am
STI
- ORD
1 stop17h 30m
American Airlines
Deal found 6/14![American Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/48:40 am
MDW
- PUJ
Nonstop4h 25m
Southwest
Wed 7/812:35 pm
PUJ
- MDW
1 stop8h 35m
Southwest
Deal found 6/11![Southwest logo]()
$579
This Arajet deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Mon 8/35:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/14![Arajet logo]()
$439
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/37:00 am
ORD
- SDQ
1 stop7h 23m
JetBlue
Tue 8/115:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/14![JetBlue logo]()
$468
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/136:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Mon 8/242:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/10![Delta logo]()
$512
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Wed 8/57:00 am
ORD
- SDQ
1 stop7h 23m
JetBlue
Wed 8/124:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/14![JetBlue logo]()
$468
This Copa Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/43:21 pm
ORD
- SDQ
1 stop20h 52m
Copa Airlines
Sat 7/1112:13 pm
SDQ
- ORD
1 stop16h 47m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$515
This Arajet deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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 7/246:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 7/266:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/13![Arajet logo]()
$484
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/48:40 am
MDW
- PUJ
Nonstop4h 25m
Southwest
Thu 7/94:55 pm
PUJ
- MDW
1 stop8h 15m
Southwest
Deal found 6/12![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Tue 9/152:56 pm
SDQ
- MDW
1 stop8h 29m
Delta
Deal found 6/15![Delta logo]()
$530
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/317:00 am
ORD
- PUJ
1 stop7h 27m
JetBlue
Tue 9/111:06 am
PUJ
- ORD
1 stop9h 19m
JetBlue
Deal found 6/14![JetBlue logo]()
$486
This Arajet deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
Mon 7/205:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 7/257:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/14![Arajet logo]()
$498
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Sat 8/226:59 pm
ORD
- POP
1 stop16h 45m
American Airlines
Wed 8/261:34 pm
POP
- ORD
1 stop10h 56m
American Airlines
Deal found 6/10![American Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/228:02 am
ORD
- POP
1 stop26h 28m
Copa Airlines
Wed 8/2612:41 pm
POP
- ORD
1 stop13h 21m
Copa Airlines
Deal found 6/10![Copa Airlines logo]()
$575
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:30 am
ORD
- SDQ
1 stop6h 58m
Delta
Tue 8/112:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/14![Delta logo]()
$530
This JetBlue deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/107:00 am
ORD
- PUJ
1 stop7h 27m
JetBlue
Thu 8/202:05 pm
PUJ
- ORD
1 stop10h 39m
JetBlue
Deal found 6/12![JetBlue logo]()
$493
This Arajet deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 7/246:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/17:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/14![Arajet logo]()
$502
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/108:49 pm
ORD
- POP
2 stops14h 44m
American Airlines
Sun 8/161:36 pm
POP
- ORD
1 stop10h 54m
American Airlines
Deal found 6/14![American Airlines logo]()
$628
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/117:35 pm
MDW
- PUJ
2 stops18h 00m
Southwest
Tue 7/141:25 pm
PUJ
- MDW
2 stops10h 50m
Southwest
Deal found 6/11![Southwest logo]()
$639
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/285:30 am
ORD
- SDQ
1 stop6h 47m
Delta
Thu 8/62:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/11![Delta logo]()
$536
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Wed 8/127:00 am
ORD
- PUJ
1 stop7h 27m
JetBlue
Wed 8/1911:24 am
PUJ
- ORD
1 stop11h 31m
JetBlue
Deal found 6/11![JetBlue logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/43:21 pm
ORD
- POP
1 stop19h 09m
Copa Airlines
Sun 8/912:41 pm
POP
- ORD
1 stop13h 21m
Copa Airlines
Deal found 6/11![Copa Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/85:00 am
ORD
- POP
1 stop8h 45m
American Airlines
Wed 7/151:26 pm
POP
- ORD
2 stops11h 35m
American Airlines
Deal found 6/10![American Airlines logo]()
$628
This Arajet deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2012:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 6/277:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/15![Arajet logo]()
$545
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/45:30 am
ORD
- SDQ
2 stops18h 24m
Delta
Tue 8/112:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/14![Delta logo]()
$555
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated June 15, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Mon 7/64:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 7/117:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/11![Arajet logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/106:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 7/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/10![Arajet logo]()
$438
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:00 am
ORD
- SDQ
1 stop6h 57m
American Airlines
Fri 7/172:20 pm
SDQ
- ORD
1 stop8h 41m
American Airlines
Deal found 6/10![American Airlines logo]()
$380
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Mon 7/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 7/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/10![Arajet logo]()
$420
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Thu 7/162:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Wed 7/225:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$431
This Super.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Fri 7/172:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Tue 7/214:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 6/11![JetBlue logo]()
$435
This Gotogate deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 7/237:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/14![Arajet logo]()
$423
This Frontier deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/208:58 pm
ORD
- PUJ
1 stop12h 44m
Frontier
Tue 7/219:29 pm
PUJ
- ORD
2 stops15h 46m
Frontier
Deal found 6/12![Frontier logo]()
$421
This Cheapflightsfares deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
Tue 7/282:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 8/65:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/13![JetBlue logo]()
$434
This Faresmojo deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Wed 7/292:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 8/65:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$427
This CheapOair deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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.
Wed 7/297:00 am
ORD
- PUJ
1 stop7h 29m
Multiple Airlines
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$442
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/11![Arajet logo]()
$433
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 June 15, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/12![Arajet logo]()
$138
This eDestinos deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/11![Arajet logo]()
$141
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/1512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/10![Arajet logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/712:44 am
ORD
- PUJ
1 stop20h 17m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/11![Arajet logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/412:29 am
ORD
- PUJ
1 stop20h 32m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1012:44 am
ORD
- PUJ
1 stop15h 47m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/712:44 am
ORD
- SDQ
1 stop16h 59m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$163
This Trip.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 9/712:29 am
ORD
- PUJ
1 stop16h 02m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:29 am
ORD
- SDQ
1 stop15h 00m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Wed 9/96:00 am
ORD
- SDQ
1 stop6h 34m
JetBlue
Deal found 6/11![JetBlue logo]()
$172
This JetBlue deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/87:00 am
ORD
- SDQ
1 stop7h 21m
JetBlue
Deal found 6/15![JetBlue logo]()
$177
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 June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $330 (Kiwi.com) |
One-way from | $138 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $637 |
Good round-trip deal | $583 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 2,558,603 searches. Data last updated June 15, 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
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 9/28
6:00 am-1:27 pm
1 stop6h 27m
Santiago de los Caballeros
Fri 10/2
3:49 pm-11:31 pm
1 stop8h 42m
$426
Quickest round-trip
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 8/1
12:12 pm-5:57 pm
Nonstop4h 45m
Punta Cana
Sat 8/8
7:02 am-11:12 am
Nonstop5h 10m
$430
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Wed 10/28
7:05 am-5:46 pm
2 stops9h 41m
Santiago de los Caballeros
Tue 11/10
6:40 am-5:34 pm
1 stop12h 54m
$431
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 8/3
5:30 am-11:15 am
Nonstop4h 45m
Punta Cana
Sat 8/8
7:02 am-11:12 am
Nonstop5h 10m
$439
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Mon 8/3
7:00 am-3:23 pm
1 stop7h 23m
Santo Domingo Las Americas
Tue 8/11
5:01 am-1:39 pm
1 stop9h 38m
$468
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 8/5
7:00 am-3:23 pm
1 stop7h 23m
Santo Domingo Las Americas
Wed 8/12
4:44 pm-11:44 pm
1 stop8h 00m
$468
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 7/24
6:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Sun 7/26
6:00 pm-10:10 pm
Nonstop5h 10m
$484
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 8/31
7:00 am-3:27 pm
1 stop7h 27m
Punta Cana
Tue 9/1
11:06 am-7:25 pm
1 stop9h 19m
$486
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 8/10
7:00 am-3:27 pm
1 stop7h 27m
Punta Cana
Thu 8/20
2:05 pm-11:44 pm
1 stop10h 39m
$493
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 7/20
5:30 am-11:15 am
Nonstop4h 45m
Punta Cana
Sat 7/25
7:02 am-11:12 am
Nonstop5h 10m
$498
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-STI
MDW-PUJ
MDW-SDQ
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-STI
MDW-PUJ
What is the cheapest month to book a flight from Chicago to Dominican Republic?
Currently, September is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $110). Flying from Chicago to Dominican Republic in July is currently the most expensive (average of $808). 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 June 15, 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 June 15, 2026.
The most flights from CHI to DO0 are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
How often are flights from Chicago to the Dominican Republic delayed?
About 19% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 138 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 morning 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 June 15, 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
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.
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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 June 15, 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 2,558,603 searches. Data last updated June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$211 | Average$426 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$511 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$226 | Average$700 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$239 | Average$427 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$348 | Average$607 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$360 | Average$597 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$503 | Average$816 | FlexibilityNo cancel fee | On-time63% |