$159+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Jun 4 — Jun 111
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Dominican Republic
Cheapest
Best
Last-minute
One-way
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 May 5, 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 May 5, 2026.
This Gotogate deal was found by Cheapflights users on 5/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 10/247:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/1![Arajet logo]()
$344
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Sat 5/165:30 pm
ORD
- PUJ
2 stops16h 05m
Frontier
Sat 5/234:37 pm
PUJ
- ORD
1 stop7h 49m
Frontier
Deal found 4/29![Frontier logo]()
$345
This Arajet deal was found by Cheapflights users on 5/2. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 10/17:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/2![Arajet logo]()
$347
This Orbitz deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Fri 7/312:44 am
ORD
- PUJ
1 stop18h 34m
Multiple Airlines
Sat 7/117:02 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$351
This Gotogate deal was found by Cheapflights users on 5/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 9/267:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/2![Arajet logo]()
$354
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/30![Arajet logo]()
$355
This Expedia deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:05 pm
ORD
- PUJ
1 stop14h 49m
Multiple Airlines
Sun 7/126:00 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Wed 5/209:29 pm
PUJ
- ORD
1 stop26h 17m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$361
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Wed 8/53:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 4/30![Frontier logo]()
$377
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Tue 8/1811:42 am
PUJ
- MDW
2 stops11h 29m
Frontier
Deal found 5/4![Frontier logo]()
$386
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Sat 6/133:40 pm
PUJ
- MDW
1 stop20h 32m
Frontier
Deal found 5/1![Frontier logo]()
$392
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Mon 8/103:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 4/30![Frontier logo]()
$393
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 May 5, 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 May 5, 2026.
This Arajet deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 5/221:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$419
This Air Canada deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:09 am
ORD
- PUJ
1 stop27h 46m
Air Canada
Sun 6/145:25 pm
PUJ
- ORD
2 stops20h 45m
Air Canada
Deal found 4/29![Air Canada logo]()
$445
This Copa Airlines deal was found by Cheapflights users on 5/2. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:02 am
ORD
- SDQ
1 stop25h 53m
Copa Airlines
Thu 7/1612:13 pm
SDQ
- ORD
1 stop16h 47m
Copa Airlines
Deal found 5/2![Copa Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 5/2612:59 pm
ORD
- STI
1 stop11h 00m
Delta
Thu 6/116:00 am
STI
- ORD
1 stop12h 11m
Delta
Deal found 4/30![Delta logo]()
$495
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Wed 5/271:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 5/4![United Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2310:31 am
ORD
- STI
2 stops9h 42m
American Airlines
Sun 5/311:21 pm
STI
- ORD
1 stop9h 18m
American Airlines
Deal found 5/5![American Airlines logo]()
$589
This Arajet deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 6/67:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/1![Arajet logo]()
$613
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:05 am
MDW
- PUJ
1 stop7h 20m
Southwest
Wed 10/211:25 pm
PUJ
- MDW
1 stop9h 50m
Southwest
Deal found 5/4![Southwest logo]()
$673
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:05 am
ORD
- SDQ
1 stop9h 56m
Delta
Mon 6/87:35 pm
SDQ
- ORD
1 stop13h 06m
Delta
Deal found 5/2![Delta logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 7/223:21 pm
ORD
- SDQ
1 stop19h 21m
Copa Airlines
Mon 7/2712:13 pm
SDQ
- ORD
1 stop16h 47m
Copa Airlines
Deal found 5/1![Copa Airlines logo]()
$515
This Arajet deal was found by Cheapflights users on 5/2. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Sun 5/241:55 pm
SDQ
- ORD
1 stop9h 15m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ORD
- SDQ
1 stop11h 01m
Delta
Tue 6/96:06 am
SDQ
- ORD
1 stop17h 28m
Delta
Deal found 5/2![Delta logo]()
$502
This United Airlines deal was found by Cheapflights users on 5/2. 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 7/308:45 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Thu 8/61:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$585
This Copa Airlines deal was found by Cheapflights users on 4/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:00 am
ORD
- POP
1 stop9h 33m
Copa Airlines
Sun 6/2112:40 pm
POP
- ORD
1 stop16h 20m
Copa Airlines
Deal found 4/30![Copa Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 5/3. 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.
Wed 5/2710:15 am
ORD
- SDQ
1 stop13h 26m
Delta
Tue 6/26:05 am
SDQ
- ORD
1 stop12h 44m
Delta
Deal found 5/3![Delta logo]()
$502
This FlightHub deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm
ORD
- PUJ
1 stop20h 12m
Multiple Airlines
Wed 9/95:05 pm
PUJ
- ORD
2 stops26h 41m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$577
This Arajet deal was found by Cheapflights users on 4/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 6/76:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/30![Arajet logo]()
$655
This Copa Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:35 am
ORD
- POP
1 stop25h 55m
Copa Airlines
Tue 11/1012:37 pm
POP
- ORD
1 stop13h 25m
Copa Airlines
Deal found 5/4![Copa Airlines logo]()
$555
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 6/18:52 pm
ORD
- POP
2 stops14h 44m
American Airlines
Fri 6/51:26 pm
POP
- ORD
2 stops12h 08m
American Airlines
Deal found 4/30![American Airlines logo]()
$673
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
ORD
- SDQ
2 stops10h 01m
Delta
Wed 6/106:06 am
SDQ
- ORD
2 stops13h 23m
Delta
Deal found 5/4![Delta logo]()
$507
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:55 pm
MDW
- PUJ
2 stops15h 50m
Southwest
Thu 10/221:25 pm
PUJ
- MDW
2 stops12h 20m
Southwest
Deal found 5/1![Southwest logo]()
$688
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/155:00 am
ORD
- PUJ
1 stop7h 11m
United Airlines
Thu 5/211:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 4/30![United Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 5/2. 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.
Wed 5/279:25 am
ORD
- SDQ
2 stops14h 16m
Delta
Mon 6/12:48 pm
SDQ
- ORD
1 stop10h 11m
Delta
Deal found 5/2![Delta logo]()
$507
This Arajet deal was found by Cheapflights users on 4/30. 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 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 4/30![Arajet logo]()
$677
This Copa Airlines deal was found by Cheapflights users on 5/3. 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 6/308:02 am
ORD
- POP
1 stop26h 29m
Copa Airlines
Tue 7/1412:37 pm
POP
- ORD
1 stop16h 23m
Copa Airlines
Deal found 5/3![Copa Airlines logo]()
$579
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:55 am
MDW
- PUJ
1 stop6h 10m
Southwest
Sun 9/132:50 pm
PUJ
- MDW
1 stop7h 30m
Southwest
Deal found 5/4![Southwest logo]()
$703
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:10 am
ORD
- POP
2 stops8h 33m
American Airlines
Tue 6/233:45 pm
POP
- ORD
1 stop8h 45m
American Airlines
Deal found 5/1![American Airlines logo]()
$713
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Sun 5/175:30 am
ORD
- PUJ
1 stop9h 00m
United Airlines
Thu 5/211:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 5/1![United Airlines logo]()
$680
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:10 am
ORD
- STI
2 stops15h 49m
Delta
Sun 6/148:59 pm
STI
- ORD
2 stops14h 51m
Delta
Deal found 5/5![Delta logo]()
$515
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 am
MDW
- PUJ
1 stop7h 40m
Southwest
Thu 9/241:45 pm
PUJ
- MDW
2 stops18h 45m
Southwest
Deal found 5/2![Southwest logo]()
$708
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated May 5, 2026 and is based on user searches.
This Arajet deal was found by Cheapflights users on 4/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 5/97:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/30![Arajet logo]()
$371
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Sat 5/1610:33 am
PUJ
- MDW
2 stops12h 29m
Frontier
Deal found 4/30![Frontier logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:56 pm
ORD
- PUJ
1 stop14h 01m
Multiple Airlines
Thu 5/212:40 pm
PUJ
- ORD
1 stop9h 35m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$369
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- PUJ
2 stops21h 38m
Frontier
Sun 5/173:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Deal found 4/30![Frontier logo]()
$414
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Sat 5/165:30 pm
ORD
- PUJ
2 stops16h 05m
Frontier
Sat 5/234:37 pm
PUJ
- ORD
1 stop7h 49m
Frontier
Deal found 4/29![Frontier logo]()
$345
This Flightnetwork deal was found by Cheapflights users on 5/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/1![Arajet logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Wed 5/209:29 pm
PUJ
- ORD
1 stop26h 17m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:52 pm
ORD
- PUJ
1 stop14h 05m
Multiple Airlines
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$367
This Frontier deal was found by Cheapflights users on 5/1. 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.
Sat 5/1611:59 am
MDW
- PUJ
1 stop25h 25m
Frontier
Sat 5/2311:45 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 5/1![Frontier logo]()
$395
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:05 am
ORD
- PUJ
1 stop7h 25m
Spirit Airlines
Thu 5/212:40 pm
PUJ
- ORD
1 stop9h 35m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$374
This Priceline deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Sat 5/307:52 pm
ORD
- PUJ
1 stop14h 05m
Frontier
Sat 6/63:35 pm
PUJ
- ORD
1 stop17h 20m
Frontier
Deal found 4/29![Frontier logo]()
$370
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Sat 6/133:40 pm
PUJ
- MDW
1 stop20h 32m
Frontier
Deal found 5/1![Frontier logo]()
$392
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 May 5, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Mytrip deal was found by Cheapflights users on 5/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/2![Arajet logo]()
$159
This Mytrip deal was found by Cheapflights users on 5/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/2![Arajet logo]()
$161
This Frontier deal was found by Cheapflights users on 5/1. 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.
Fri 6/58:00 pm
ORD
- PUJ
1 stop13h 57m
Frontier
Deal found 5/1![Frontier logo]()
$164
This Arajet deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 10/264:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/29![Arajet logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:00 pm
ORD
- PUJ
1 stop13h 57m
Frontier
Deal found 5/4![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Deal found 4/30![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:52 pm
ORD
- PUJ
1 stop14h 05m
Frontier
Deal found 4/30![Frontier logo]()
$168
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:00 pm
ORD
- SDQ
1 stop14h 05m
Frontier
Deal found 5/4![Frontier logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:52 pm
ORD
- PUJ
1 stop14h 05m
Frontier
Deal found 4/30![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Mon 10/125:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/2![Arajet logo]()
$172
This Expedia deal was found by Cheapflights users on 4/30. 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.
Tue 5/2612:33 am
ORD
- PUJ
1 stop18h 46m
Frontier
Deal found 4/30![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/256:00 am
MDW
- PUJ
2 stops31h 17m
Frontier
Deal found 4/29![Frontier logo]()
$175
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $344 (Gotogate) |
One-way from | $159 (Mytrip) |
Popular in | March |
Cheapest in | September |
Average price | $498 |
Good round-trip deal | $455 or less |
Good one-way deal | $238 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 May 5, 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 - SDQ
ORDSDQ
Chicago O'Hare Intl
Sat 5/16
12:12 pm-9:40 pm
1 stop8h 28m
Santo Domingo Las Americas
Fri 5/22
1:40 am-11:12 am
1 stop10h 32m
$419
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 6/7
7:09 am-11:55 am
1 stop27h 46m
Punta Cana
Sun 6/14
5:25 pm-1:10 pm
2 stops20h 45m
$445
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 7/8
8:02 am-10:55 am
1 stop25h 53m
Santo Domingo Las Americas
Thu 7/16
12:13 pm-4:00 am
1 stop16h 47m
$490
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Tue 5/26
12:59 pm-12:59 am
1 stop11h 00m
Santiago de los Caballeros
Thu 6/11
6:00 am-5:11 pm
1 stop12h 11m
$495
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Thu 5/28
7:05 am-6:01 pm
1 stop9h 56m
Santo Domingo Las Americas
Mon 6/8
7:35 pm-7:41 am
1 stop13h 06m
$502
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Thu 5/28
6:00 am-6:01 pm
1 stop11h 01m
Santo Domingo Las Americas
Tue 6/9
6:06 am-10:34 pm
1 stop17h 28m
$502
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 5/27
10:15 am-12:41 am
1 stop13h 26m
Santo Domingo Las Americas
Tue 6/2
6:05 am-5:49 pm
1 stop12h 44m
$502
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 6/3
7:00 am-6:01 pm
2 stops10h 01m
Santo Domingo Las Americas
Wed 6/10
6:06 am-6:29 pm
2 stops13h 23m
$507
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 5/27
9:25 am-12:41 am
2 stops14h 16m
Santo Domingo Las Americas
Mon 6/1
2:48 pm-11:59 pm
1 stop10h 11m
$507
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 7/22
3:21 pm-11:42 am
1 stop19h 21m
Santo Domingo Las Americas
Mon 7/27
12:13 pm-4:00 am
1 stop16h 47m
$515
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-STI
ORD-PUJ
MDW-PUJ
ORD-POP
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-STI
ORD-PUJ
MDW-PUJ
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 19 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Dominican Republic?
Currently, August is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $109). Flying from Chicago to Dominican Republic in March is currently the most expensive (average of $668). 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 May 5, 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 May 5, 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 20% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 136 minutes.
What is the most punctual flight time for Chicago to the Dominican Republic flights?
Historically, flights departing in the early afternoon 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.
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 May 5, 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
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top regions
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 May 5, 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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$527 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$398 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$193 | Average$511 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$209 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$220 | Average$442 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$260 | Average$428 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$274 | Average$567 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$348 | Average$587 | FlexibilityNo cancel fee | On-time69% |