$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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Apr 16 — Apr 231
Round-trip
1 adult, Economy
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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 März 17, 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 März 17, 2026.
This eDestinos deal was found by Cheapflights users on 3/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/167:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Mo 5/184:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/13![Arajet logo]()
$261
This Arajet deal was found by Cheapflights users on 3/14. 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.
Do 4/163:30 pm
SDQ
- ORD
1 stop9h 10m
Multiple Airlines
Mo 4/274:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$290
This Arajet deal was found by Cheapflights users on 3/13. 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.
Do 4/161:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Mo 4/204:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 10/107:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Fr 10/166:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/14![Arajet logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/237:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Fr 5/16:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/17![Arajet logo]()
$309
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/153:35 pm
PUJ
- ORD
1 stop19h 03m
United Airlines
So 5/109:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Deal found 3/12![United Airlines logo]()
$322
This Arajet deal was found by Cheapflights users on 3/13. 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.
Fr 5/151:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Mo 5/184:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 3/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/112:06 pm
PUJ
- ORD
Nonstop5h 19m
American Airlines
Di 5/56:57 am
ORD
- PUJ
1 stop8h 28m
American Airlines
Deal found 3/13![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 3/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/112:06 pm
PUJ
- ORD
Nonstop5h 19m
American Airlines
Mo 5/49:45 am
ORD
- PUJ
Nonstop4h 39m
American Airlines
Deal found 3/15![American Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/98:30 am
PUJ
- ORD
2 stops16h 06m
Multiple Airlines
Mo 4/274:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/77:00 am
PUJ
- ORD
1 stop23h 45m
Multiple Airlines
Mo 4/274:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/14:40 pm
PUJ
- ORD
1 stop15h 46m
United Airlines
Mo 5/411:00 pm
ORD
- PUJ
1 stop15h 30m
United Airlines
Deal found 3/15![United Airlines logo]()
$338
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 März 17, 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 März 17, 2026.
This Arajet deal was found by Cheapflights users on 3/13. 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.
Do 4/161:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Mo 4/204:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$301
This FlightHub deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/167:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Mo 5/184:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/17![Arajet logo]()
$315
This American Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/15:25 pm
PUJ
- ORD
1 stop8h 00m
American Airlines
Di 5/56:57 am
ORD
- PUJ
1 stop8h 28m
American Airlines
Deal found 3/17![American Airlines logo]()
$340
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/83:28 pm
STI
- ORD
1 stop8h 49m
Spirit Airlines
Mo 4/135:05 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/11:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Di 5/59:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Deal found 3/15![United Airlines logo]()
$397
This Frontier deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/21:37 pm
PUJ
- MDW
2 stops9h 37m
Frontier
Mi 5/66:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 3/16![Frontier logo]()
$442
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/18:59 pm
STI
- ORD
2 stops16h 50m
Delta
Mi 5/611:19 am
ORD
- STI
2 stops12h 03m
Delta
Deal found 3/12![Delta logo]()
$498
This Copa Airlines deal was found by Cheapflights users on 3/13. 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.
Fr 7/316:42 pm
SDQ
- ORD
1 stop10h 18m
Copa Airlines
Sa 8/88:02 am
ORD
- SDQ
1 stop17h 23m
Copa Airlines
Deal found 3/13![Copa Airlines logo]()
$508
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 6/265:05 pm
PUJ
- ORD
2 stops22h 50m
Air Canada
Sa 7/118:45 am
ORD
- PUJ
1 stop30h 20m
Air Canada
Deal found 3/13![Air Canada logo]()
$541
This Southwest deal was found by Cheapflights users on 3/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/1612:55 pm
PUJ
- MDW
Nonstop5h 00m
Southwest
Mo 5/185:35 am
MDW
- PUJ
1 stop6h 30m
Southwest
Deal found 3/13![Southwest logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 8/2612:41 pm
SDQ
- ORD
1 stop12h 44m
Multiple Airlines
Sa 8/2912:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$375
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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.
Fr 5/13:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
Mi 5/67:15 pm
ORD
- STI
1 stop17h 47m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$426
This Arajet deal was found by Cheapflights users on 3/12. 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.
Do 7/231:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Mo 7/275:30 am
ORD
- SDQ
1 stop10h 25m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$393
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/21:37 pm
PUJ
- MDW
2 stops9h 37m
Frontier
Di 5/56:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 3/13![Frontier logo]()
$443
This Copa Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/1312:08 pm
SDQ
- ORD
1 stop14h 05m
Copa Airlines
Fr 4/178:06 am
ORD
- SDQ
1 stop13h 41m
Copa Airlines
Deal found 3/16![Copa Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/149:38 am
PUJ
- MDW
2 stops10h 53m
Multiple Airlines
Di 4/217:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/286:00 am
STI
- ORD
1 stop12h 41m
Delta
Di 5/56:04 am
ORD
- STI
1 stop12h 29m
Delta
Deal found 3/13![Delta logo]()
$522
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/222:20 pm
PUJ
- ORD
1 stop11h 25m
United Airlines
Mi 5/209:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Deal found 3/12![United Airlines logo]()
$527
This Spirit Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/12:52 am
SDQ
- ORD
1 stop9h 25m
Spirit Airlines
Mo 4/67:17 am
ORD
- SDQ
1 stop28h 58m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$481
This eDestinos deal was found by Cheapflights users on 3/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/142:20 pm
PUJ
- MDW
2 stops30h 11m
Frontier
Di 4/212:15 pm
MDW
- PUJ
2 stops22h 05m
Frontier
Deal found 3/15![Frontier logo]()
$494
This Copa Airlines deal was found by Cheapflights users on 3/13. 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.
Di 5/122:14 pm
SDQ
- ORD
1 stop12h 01m
Copa Airlines
Do 9/108:01 am
ORD
- SDQ
1 stop13h 55m
Copa Airlines
Deal found 3/13![Copa Airlines logo]()
$508
This Gotogate deal was found by Cheapflights users on 3/14. 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.
Di 3/317:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sa 4/412:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/14![Arajet logo]()
$571
This Delta deal was found by Cheapflights users on 3/14. 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.
Sa 5/166:00 am
STI
- ORD
1 stop16h 56m
Delta
Di 5/198:10 am
ORD
- STI
2 stops15h 49m
Delta
Deal found 3/14![Delta logo]()
$522
This Priceline deal was found by Cheapflights users on 3/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 4/263:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
So 5/35:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$500
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/158:59 pm
STI
- ORD
2 stops14h 30m
Delta
Di 5/198:10 am
ORD
- STI
2 stops15h 49m
Delta
Deal found 3/16![Delta logo]()
$522
This Copa Airlines deal was found by Cheapflights users on 3/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/156:39 pm
SDQ
- ORD
1 stop20h 27m
Copa Airlines
Di 5/198:02 am
ORD
- SDQ
1 stop13h 54m
Copa Airlines
Deal found 3/15![Copa Airlines logo]()
$539
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
So 4/266:00 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
So 5/312:38 pm
ORD
- PUJ
2 stops30h 30m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$496
This CheapOair deal was found by Cheapflights users on 3/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/163:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Mo 5/184:52 pm
MDW
- PUJ
2 stops26h 27m
Frontier
Deal found 3/15![Frontier logo]()
$562
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/21:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Di 5/59:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Deal found 3/15![United Airlines logo]()
$638
This Southwest deal was found by Cheapflights users on 3/12. 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.
Mo 4/272:05 pm
PUJ
- MDW
1 stop11h 00m
Southwest
Mo 5/47:30 am
MDW
- PUJ
1 stop6h 30m
Southwest
Deal found 3/12![Southwest logo]()
$705
Last-minute flights from Dominican Republic to ChicagoDiscover last-minute flight deals from Dominican Republic to Chicago. Data last updated März 17, 2026 and is based on user searches.
Discover last-minute flight deals from Dominican Republic to Chicago. Data last updated März 17, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 3/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 3/319:40 pm
PUJ
- ORD
1 stop21h 10m
Multiple Airlines
Mo 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$365
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/77:00 am
PUJ
- ORD
1 stop23h 45m
Multiple Airlines
Mo 4/274:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$336
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/83:28 pm
STI
- ORD
1 stop8h 49m
Spirit Airlines
Mo 4/135:05 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/98:30 am
PUJ
- ORD
2 stops16h 06m
Multiple Airlines
Mo 4/274:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/154:40 pm
PUJ
- ORD
1 stop15h 46m
United Airlines
So 5/108:45 am
ORD
- PUJ
1 stop26h 55m
United Airlines
Deal found 3/12![United Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 4/152:35 pm
SDQ
- ORD
1 stop10h 49m
Multiple Airlines
Mi 4/226:08 pm
ORD
- SDQ
2 stops45h 21m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$369
This Arajet deal was found by Cheapflights users on 3/14. 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.
Do 4/163:30 pm
SDQ
- ORD
1 stop9h 10m
Multiple Airlines
Mo 4/274:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$290
This Arajet deal was found by Cheapflights users on 3/13. 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.
Do 4/161:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Mo 4/204:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/217:00 am
PUJ
- ORD
3 stops28h 02m
Multiple Airlines
Sa 4/2512:12 pm
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/237:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Fr 5/16:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/17![Arajet logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/272:35 pm
SDQ
- ORD
1 stop20h 01m
Multiple Airlines
Mo 5/44:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$355
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Sa 5/3011:05 am
ORD
- PUJ
1 stop25h 50m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$368
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 März 17, 2026.
Search for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated März 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/97:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/13![Arajet logo]()
$167
This eDestinos deal was found by Cheapflights users on 3/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
So 5/106:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$169
This Booking.com deal was found by Cheapflights users on 3/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$175
This Arajet deal was found by Cheapflights users on 3/12. 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.
Do 4/301:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Mo 4/133:01 pm
SDQ
- MDW
2 stops29h 30m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 9/107:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/13![Arajet logo]()
$186
This eDestinos deal was found by Cheapflights users on 3/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 3/232:52 am
SDQ
- ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$188
This Booking.com deal was found by Cheapflights users on 3/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/257:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$191
This FlightHub deal was found by Cheapflights users on 3/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 8/137:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/142:20 pm
SDQ
- ORD
1 stop20h 16m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Mo 4/133:01 pm
SDQ
- ORD
2 stops44h 22m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 4/73:28 pm
STI
- ORD
1 stop27h 42m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$197
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 März 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (eDestinos) |
One-way from | $167 (Kiwi.com) |
Popular in | June |
Cheapest in | May |
Average price | $310 |
Good round-trip deal | $283 or less |
Good one-way deal | $211 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 März 17, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Do 4/16
1:45 pm-11:40 pm
1 stop10h 55m
Chicago O'Hare Intl
Mo 4/20
4:30 am-4:55 pm
1 stop11h 25m
$301
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sa 5/16
7:02 am-11:12 am
Nonstop5h 10m
Chicago O'Hare Intl
Mo 5/18
4:30 am-10:15 am
Nonstop4h 45m
$315
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Fr 5/1
5:25 pm-12:25 am
1 stop8h 00m
Chicago O'Hare Intl
Di 5/5
6:57 am-4:25 pm
1 stop8h 28m
$340
Santiago de los CaballerosChicago
STI - ORD
STIORD
Santiago de los Caballeros
Mi 4/8
3:28 pm-11:17 pm
1 stop8h 49m
Chicago O'Hare Intl
Mo 4/13
5:05 am-2:23 pm
1 stop8h 18m
$370
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Mi 8/26
12:41 pm-12:25 am
1 stop12h 44m
Chicago O'Hare Intl
Sa 8/29
12:12 pm-9:40 pm
1 stop8h 28m
$375
Santo DomingoChicago
SDQ - ORD
SDQORD
Santo Domingo Las Americas
Do 7/23
1:45 pm-11:40 pm
1 stop10h 55m
Chicago O'Hare Intl
Mo 7/27
5:30 am-4:55 pm
1 stop10h 25m
$393
Quickest round-trip
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Fr 5/1
1:50 pm-5:59 pm
Nonstop5h 09m
Chicago O'Hare Intl
Di 5/5
9:30 am-3:12 pm
Nonstop4h 42m
$397
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Di 4/14
9:38 am-7:31 pm
2 stops10h 53m
Chicago Midway
Di 4/21
7:30 am-4:19 pm
1 stop7h 49m
$420
Santiago de los CaballerosChicago
STI - ORD
STIORD
Santiago de los Caballeros
Fr 5/1
3:07 pm-12:24 am
1 stop10h 17m
Chicago O'Hare Intl
Mi 5/6
7:15 pm-2:02 pm
1 stop17h 47m
$426
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Sa 5/2
1:37 pm-10:14 pm
2 stops9h 37m
Chicago Midway
Mi 5/6
6:00 am-2:24 pm
1 stop7h 24m
$442
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
SDQ-MDW
STI-ORD
PUJ-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
SDQ-MDW
STI-ORD
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 June is currently the most expensive (average of $334). 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 März 17, 2026.
It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 54% 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 März 17, 2026.
The most flights from DO0 to CHI are scheduled on a Saturday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 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 März 17, 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.
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.9
Food
6.4
Boarding
7.5
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Comfort
7.2
Crew
7.9
Overall
7.1
Entertainment
6.9
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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Complete your trip
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Alternative routes for Dominican Republic to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on März 17, 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 März 17, 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 März 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$181 | Average$412 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$189 | Average$341 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$191 | Average$714 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$478 | FlexibilityNo cancel fee | On-time71% |