$167+ Cheap flights from the Dominican Republic to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Dominican Republic to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Dominican Republic to Chicago
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Cheapest flights from Dominican Republic to ChicagoExplore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
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 5/234:37 pm
PUJ
- ORD
1 stop7h 49m
Frontier
Sat 5/307:52 pm
ORD
- PUJ
1 stop14h 05m
Frontier
Deal found 4/30![Frontier logo]()
$327
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.
Thu 12/247:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Fri 1/15:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/30![Arajet logo]()
$340
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Mon 9/75:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/30![Arajet logo]()
$353
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.
Thu 10/297:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 10/3111:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/29![Arajet logo]()
$359
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.
Sat 5/234:37 pm
PUJ
- ORD
1 stop7h 49m
Multiple Airlines
Sat 5/306:22 pm
ORD
- PUJ
2 stops20h 03m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$368
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.
Thu 9/37:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Sun 9/612:29 am
ORD
- PUJ
1 stop18h 49m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$392
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:44 pm
PUJ
- ORD
1 stop17h 09m
Frontier
Tue 8/41:50 pm
ORD
- PUJ
1 stop23h 44m
Frontier
Deal found 4/30![Frontier logo]()
$403
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 5/274:37 pm
PUJ
- ORD
1 stop7h 49m
Frontier
Fri 6/58:00 pm
ORD
- PUJ
1 stop13h 57m
Frontier
Deal found 4/30![Frontier logo]()
$405
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.
Wed 5/1312:41 pm
SDQ
- ORD
1 stop28h 08m
Multiple Airlines
Mon 9/75:30 am
ORD
- SDQ
1 stop10h 25m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$416
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:41 pm
SDQ
- ORD
1 stop11h 05m
Multiple Airlines
Sat 5/231:50 pm
ORD
- SDQ
2 stops22h 49m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$430
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.
Thu 7/93:30 pm
SDQ
- ORD
1 stop9h 10m
Multiple Airlines
Mon 8/315:30 am
ORD
- SDQ
1 stop10h 25m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$448
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.
Fri 6/193:52 pm
STI
- ORD
1 stop9h 07m
Multiple Airlines
Sat 6/208:00 pm
ORD
- STI
1 stop12h 54m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$458
Best flights from Dominican Republic to ChicagoDiscover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
Discover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
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.
Thu 10/297:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 10/3111:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/29![Arajet logo]()
$359
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:37 pm
PUJ
- ORD
1 stop7h 49m
Multiple Airlines
Sat 5/305:35 pm
ORD
- PUJ
2 stops19h 20m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$372
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 8/2911:42 am
PUJ
- MDW
2 stops11h 29m
Frontier
Tue 9/16:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Deal found 4/29![Frontier logo]()
$475
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/144:01 pm
SDQ
- ORD
1 stop17h 21m
Spirit Airlines
Fri 6/267:07 pm
ORD
- SDQ
1 stop17h 02m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$522
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.
Fri 10/98:31 pm
STI
- ORD
2 stops16h 35m
Delta
Tue 10/137:10 am
ORD
- STI
2 stops10h 56m
Delta
Deal found 5/3![Delta logo]()
$547
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.
Thu 9/242:16 pm
SDQ
- ORD
1 stop11h 46m
Copa Airlines
Sun 9/278:01 am
ORD
- SDQ
1 stop25h 54m
Copa Airlines
Deal found 5/3![Copa Airlines logo]()
$592
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:45 pm
PUJ
- MDW
2 stops9h 10m
Southwest
Mon 9/77:55 pm
MDW
- PUJ
2 stops16h 25m
Southwest
Deal found 4/30![Southwest logo]()
$648
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:32 pm
STI
- ORD
1 stop11h 02m
American Airlines
Tue 10/138:34 pm
ORD
- STI
2 stops14h 36m
American Airlines
Deal found 5/3![American Airlines logo]()
$651
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 8/2212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/3![Arajet logo]()
$425
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:29 pm
PUJ
- MDW
2 stops38h 38m
Frontier
Sat 8/226:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Deal found 5/4![Frontier logo]()
$486
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 11/710:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 5/4![Arajet logo]()
$483
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:07 pm
PUJ
- ORD
2 stops44h 48m
Multiple Airlines
Sat 6/135:29 pm
ORD
- PUJ
2 stops51h 00m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$551
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
STI
- ORD
1 stop12h 11m
Delta
Thu 7/309:45 am
ORD
- STI
2 stops15h 10m
Delta
Deal found 4/29![Delta logo]()
$570
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.
Sat 7/43:52 pm
STI
- ORD
1 stop18h 30m
Spirit Airlines
Mon 7/275:10 am
ORD
- STI
1 stop9h 05m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$573
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.
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 5/3012:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/29![Arajet logo]()
$511
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
STI
- ORD
1 stop12h 11m
Delta
Thu 7/309:45 am
ORD
- STI
2 stops15h 10m
Delta
Deal found 4/29![Delta logo]()
$570
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Sun 5/316:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 5/2![Frontier logo]()
$579
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.
Mon 6/154:15 pm
STI
- ORD
2 stops21h 08m
Spirit Airlines
Sat 6/205:10 am
ORD
- STI
1 stop8h 35m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$595
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:59 pm
STI
- ORD
1 stop13h 26m
Delta
Thu 7/309:45 am
ORD
- STI
2 stops15h 10m
Delta
Deal found 4/29![Delta logo]()
$570
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:44 pm
STI
- ORD
1 stop9h 42m
American Airlines
Mon 7/276:10 am
ORD
- STI
1 stop7h 34m
American Airlines
Deal found 5/3![American Airlines logo]()
$697
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.
Thu 9/31:05 pm
PUJ
- MDW
1 stop9h 41m
Delta
Mon 9/76:00 am
MDW
- PUJ
1 stop6h 27m
Delta
Deal found 4/30![Delta logo]()
$570
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 8/272:53 pm
SDQ
- ORD
1 stop10h 05m
Delta
Tue 9/17:10 am
ORD
- SDQ
2 stops9h 54m
Delta
Deal found 5/2![Delta logo]()
$585
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/233:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Sun 6/286:00 am
MDW
- PUJ
2 stops13h 18m
Frontier
Deal found 4/29![Frontier logo]()
$712
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.
Sun 7/262:42 pm
SDQ
- ORD
1 stop8h 26m
Delta
Mon 8/35:28 am
ORD
- SDQ
1 stop7h 00m
Delta
Deal found 5/4![Delta logo]()
$596
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:59 pm
STI
- ORD
2 stops15h 45m
Delta
Tue 7/289:45 am
ORD
- STI
2 stops15h 10m
Delta
Deal found 4/29![Delta logo]()
$600
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.
Fri 6/126:06 am
SDQ
- ORD
2 stops13h 23m
Delta
Tue 6/166:05 am
ORD
- SDQ
1 stop10h 59m
Delta
Deal found 5/4![Delta logo]()
$613
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.
Thu 6/116:06 am
SDQ
- ORD
2 stops15h 25m
Delta
Wed 6/175:30 am
ORD
- SDQ
1 stop6h 46m
Delta
Deal found 5/4![Delta logo]()
$613
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:56 pm
SDQ
- MDW
1 stop7h 49m
Delta
Tue 10/136:00 am
MDW
- SDQ
1 stop6h 41m
Delta
Deal found 5/1![Delta logo]()
$613
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 5/202:49 pm
SDQ
- ORD
1 stop8h 04m
Delta
Sun 5/2412:59 pm
ORD
- SDQ
1 stop10h 42m
Delta
Deal found 5/3![Delta logo]()
$614
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:48 pm
SDQ
- MDW
1 stop7h 21m
Delta
Tue 5/269:22 am
MDW
- SDQ
2 stops14h 19m
Delta
Deal found 5/1![Delta logo]()
$614
Last-minute flights from Dominican Republic to ChicagoDiscover last-minute flight deals from Dominican Republic to Chicago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Dominican Republic to Chicago. Data last updated May 4, 2026 and is based on user searches.
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.
Wed 5/1312:41 pm
SDQ
- ORD
1 stop28h 08m
Multiple Airlines
Mon 9/75:30 am
ORD
- SDQ
1 stop10h 25m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$416
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.
Wed 5/134:25 pm
PUJ
- ORD
1 stop17h 35m
Multiple Airlines
Sat 5/307:52 pm
ORD
- PUJ
1 stop14h 05m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$419
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/134:25 pm
PUJ
- ORD
1 stop17h 35m
Air Canada
Sat 5/306:22 pm
ORD
- PUJ
2 stops18h 33m
Air Canada
Deal found 5/4![Air Canada logo]()
$460
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.
Fri 5/1510:19 am
SDQ
- ORD
1 stop14h 37m
Multiple Airlines
Sat 5/3012:59 pm
ORD
- SDQ
2 stops14h 01m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$487
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.
Fri 5/1510:19 am
SDQ
- ORD
1 stop14h 37m
Multiple Airlines
Tue 5/193:55 pm
ORD
- SDQ
2 stops23h 34m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$488
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:41 pm
SDQ
- ORD
1 stop11h 05m
Multiple Airlines
Sat 5/231:50 pm
ORD
- SDQ
2 stops22h 49m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$430
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.
Wed 5/2712:41 pm
SDQ
- ORD
1 stop28h 08m
Multiple Airlines
Thu 6/41:49 pm
ORD
- SDQ
1 stop25h 41m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$460
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.
Thu 5/2811:45 am
PUJ
- MDW
2 stops11h 17m
Frontier
Sun 5/316:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 4/30![Frontier logo]()
$473
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.
Sat 5/303:17 pm
STI
- ORD
1 stop8h 58m
Spirit Airlines
Sat 6/65:05 am
ORD
- STI
1 stop8h 07m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$472
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:10 am
SDQ
- ORD
1 stop17h 24m
Multiple Airlines
Sat 6/138:00 pm
ORD
- SDQ
1 stop14h 06m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$485
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/123:35 pm
PUJ
- MDW
1 stop20h 29m
Frontier
Mon 6/156:00 am
MDW
- PUJ
1 stop7h 25m
Frontier
Deal found 4/30![Frontier logo]()
$462
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/263:35 pm
PUJ
- MDW
1 stop20h 29m
Frontier
Mon 6/296:00 am
MDW
- PUJ
1 stop7h 25m
Frontier
Deal found 5/1![Frontier logo]()
$488
One-way flights from Dominican Republic to ChicagoSearch for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
Search for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:30 pm
SDQ
- ORD
1 stop8h 56m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$167
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.
Fri 5/2911:45 am
PUJ
- MDW
2 stops35h 17m
Frontier
Deal found 5/4![Frontier logo]()
$196
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/2![Arajet logo]()
$196
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.
Tue 5/2611:45 am
PUJ
- MDW
2 stops35h 17m
Frontier
Deal found 5/4![Frontier logo]()
$198
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.
Tue 5/2611:45 am
PUJ
- ORD
2 stops32h 56m
Frontier
Deal found 4/29![Frontier logo]()
$204
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.
Fri 5/2911:45 am
PUJ
- ORD
2 stops31h 59m
Frontier
Deal found 5/2![Frontier logo]()
$205
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:40 am
SDQ
- ORD
1 stop9h 17m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$208
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.
Sat 5/2311:45 am
PUJ
- MDW
2 stops35h 17m
Frontier
Deal found 5/4![Frontier logo]()
$209
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.
Fri 5/229:29 pm
PUJ
- ORD
1 stop26h 57m
Frontier
Deal found 4/30![Frontier logo]()
$210
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.
Fri 5/292:40 pm
PUJ
- MDW
2 stops21h 24m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$212
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.
Mon 6/13:35 pm
PUJ
- ORD
1 stop17h 20m
Frontier
Deal found 4/30![Frontier logo]()
$212
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:35 pm
PUJ
- ORD
1 stop17h 20m
Frontier
Deal found 5/1![Frontier logo]()
$213
Find flight deals from Dominican Republic to Chicago
Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Frontier) |
One-way from | $167 (Trip.com) |
Popular in | March |
Cheapest in | November |
Average price | $400 |
Good round-trip deal | $445 or less |
Good one-way deal | $279 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Dominican Republic to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 4, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Thu 10/29
7:30 pm-11:40 pm
Nonstop5h 10m
Chicago O'Hare Intl
Sat 10/31
11:27 am-5:12 pm
Nonstop4h 45m
$359
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sat 5/23
4:37 pm-11:26 pm
1 stop7h 49m
Chicago O'Hare Intl
Sat 5/30
5:35 pm-1:55 pm
2 stops19h 20m
$372
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Thu 8/13
7:30 pm-11:40 pm
Nonstop5h 10m
Chicago O'Hare Intl
Sat 8/22
12:12 pm-5:57 pm
Nonstop4h 45m
$425
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Sat 8/29
11:42 am-10:11 pm
2 stops11h 29m
Chicago Midway
Tue 9/1
6:00 am-2:29 pm
1 stop7h 29m
$475
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Thu 10/29
7:30 pm-11:40 pm
Nonstop5h 10m
Chicago O'Hare Intl
Sat 11/7
10:27 am-5:12 pm
Nonstop4h 45m
$483
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Thu 8/13
9:29 pm-11:07 am
2 stops38h 38m
Chicago Midway
Sat 8/22
6:00 am-2:29 pm
1 stop7h 29m
$486
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sat 5/23
7:02 am-11:12 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 5/30
12:12 pm-5:57 pm
Nonstop4h 45m
$511
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Sun 6/14
4:01 pm-8:22 am
1 stop17h 21m
Chicago O'Hare Intl
Fri 6/26
7:07 pm-1:09 pm
1 stop17h 02m
$522
Santiago de los CaballerosChicago
STI - ORD
STIORD
Santiago de los Caballeros
Fri 10/9
8:31 pm-12:06 pm
2 stops16h 35m
Chicago O'Hare Intl
Tue 10/13
7:10 am-7:06 pm
2 stops10h 56m
$547
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sat 5/30
12:07 pm-7:55 am
2 stops44h 48m
Chicago O'Hare Intl
Sat 6/13
5:29 pm-9:29 pm
2 stops51h 00m
$551
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Dominican Republic to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
PUJ-ORD
SDQ-ORD
PUJ-MDW
STI-ORD
SDQ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from the Dominican Republic to Chicago
DO0-CHI
PUJ-ORD
SDQ-ORD
PUJ-MDW
STI-ORD
How far ahead should I book a flight from Dominican Republic to Chicago?
The best time to book flights from Dominican Republic to Chicago is 52 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Dominican Republic to Chicago?
Currently, August is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $139). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $224). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from DO to CHI?
Find hourly flight availability from Dominican Republic to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2026.
It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 53% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Dominican Republic to Chicago
Explore weekly flight availability from Dominican Republic to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 4, 2026.
The most flights from DO0 to CHI are scheduled on a Sunday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 4, 2026.
Peruse reviews from past customers who have flown with American Airlines from the Dominican Republic to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Comfort
7.2
Entertainment
6.9
Overall
7.1
Food
6.4
Boarding
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Crew
7.9
Comfort
7.2
Entertainment
6.9
Overall
7.1
Food
6.4
Boarding
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Dominican Republic to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Dominican Republic to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Dominican Republic to Chicago by cabin class
Find flights from Dominican Republic to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Dominican Republic and Chicago flights
Browse other Dominican Republic and Chicago flight options. Last updated on May 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Dominican Republic to Chicago
Discover the top 4 airlines that operate flights from Dominican Republic to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$189 | Average$330 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$195 | Average$380 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$527 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$449 | Average$714 | FlexibilityNo cancel fee | On-timeN/A |