$121+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
abr. 16 — abr. 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Dominican Republic with Cheapflights
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Cheapest flights from Chicago to Dominican RepublicExplore the most affordable flight options available from Chicago to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marzo 17, 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 marzo 17, 2026.
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.
sáb. 10/3111:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
dom. 11/86:10 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/14![Arajet logo]()
$292
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.
lun. 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/16![Arajet logo]()
$293
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/1112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/13![Arajet logo]()
$296
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
sáb. 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/12![Arajet logo]()
$299
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/176:04 pm
ORD
- PUJ
1 stop14h 53m
Multiple Airlines
sáb. 4/257:02 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$300
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.
sáb. 4/2512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$302
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.
sáb. 4/1812:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$303
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.
lun. 4/274:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
jue. 4/303:30 pm
SDQ
- ORD
1 stop9h 10m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$303
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
dom. 9/136:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/13![Arajet logo]()
$304
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/127:00 am
ORD
- PUJ
Nonstop4h 46m
Multiple Airlines
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$306
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/44:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
sáb. 5/97:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/14![Arajet logo]()
$307
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
sáb. 4/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/14![Arajet logo]()
$308
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 marzo 17, 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 marzo 17, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/87:17 am
ORD
- STI
1 stop6h 06m
Spirit Airlines
vie. 4/102:46 am
STI
- ORD
1 stop9h 31m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$390
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/33:05 pm
ORD
- SDQ
1 stop18h 49m
Copa Airlines
lun. 4/1312:38 pm
SDQ
- ORD
1 stop13h 35m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$419
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.
lun. 4/278:50 pm
ORD
- STI
2 stops14h 33m
American Airlines
lun. 5/41:32 pm
STI
- ORD
2 stops18h 57m
American Airlines
Deal found 3/13![American Airlines logo]()
$473
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/267:00 am
ORD
- STI
2 stops16h 59m
Delta
jue. 6/116:15 am
STI
- ORD
2 stops11h 21m
Delta
Deal found 3/15![Delta logo]()
$476
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.
mar. 5/125:00 am
ORD
- PUJ
1 stop7h 11m
United Airlines
mar. 5/191:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 3/12![United Airlines logo]()
$491
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/294:36 pm
ORD
- SDQ
1 stop8h 02m
Multiple Airlines
sáb. 4/411:40 am
SDQ
- ORD
1 stop25h 13m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$528
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.
sáb. 5/166:10 am
MDW
- PUJ
1 stop7h 05m
Southwest
sáb. 5/2312:55 pm
PUJ
- MDW
Nonstop5h 00m
Southwest
Deal found 3/12![Southwest logo]()
$551
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.
sáb. 4/188:31 am
ORD
- POP
1 stop27h 16m
JetBlue
jue. 4/233:21 pm
POP
- ORD
1 stop17h 20m
JetBlue
Deal found 3/15![JetBlue logo]()
$604
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/148:06 am
ORD
- SDQ
1 stop13h 41m
Copa Airlines
mié. 4/298:43 am
SDQ
- ORD
1 stop17h 30m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$419
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.
lun. 4/63:05 pm
ORD
- SDQ
1 stop10h 15m
Copa Airlines
lun. 4/1312:08 pm
SDQ
- ORD
1 stop14h 05m
Copa Airlines
Deal found 3/13![Copa Airlines logo]()
$419
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.
lun. 4/276:00 am
MDW
- PUJ
1 stop7h 32m
Delta
jue. 4/302:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 3/12![Delta logo]()
$479
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/235:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
dom. 5/313:07 pm
STI
- ORD
1 stop10h 20m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$483
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/99:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
mié. 5/131:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 3/13![United Airlines logo]()
$506
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/193:21 pm
ORD
- SDQ
1 stop19h 21m
Copa Airlines
dom. 5/248:45 am
SDQ
- ORD
1 stop17h 30m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$419
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.
vie. 4/176:00 am
MDW
- SDQ
1 stop6h 12m
Delta
sáb. 4/252:37 pm
SDQ
- MDW
1 stop8h 51m
Delta
Deal found 3/12![Delta logo]()
$479
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.
vie. 4/106:10 pm
ORD
- STI
1 stop6h 39m
Spirit Airlines
lun. 4/133:28 pm
STI
- ORD
1 stop8h 49m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$485
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/258:35 pm
MDW
- PUJ
2 stops16h 40m
Southwest
jue. 5/282:05 pm
PUJ
- MDW
2 stops18h 05m
Southwest
Deal found 3/15![Southwest logo]()
$563
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/135:00 am
ORD
- PUJ
1 stop7h 11m
United Airlines
jue. 5/211:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 3/13![United Airlines logo]()
$532
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/171:06 pm
ORD
- STI
1 stop10h 16m
Delta
mar. 4/286:00 am
STI
- ORD
1 stop16h 57m
Delta
Deal found 3/15![Delta logo]()
$489
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/128:46 pm
ORD
- POP
2 stops16h 44m
American Airlines
vie. 5/153:30 pm
POP
- ORD
2 stops16h 59m
American Airlines
Deal found 3/12![American Airlines logo]()
$605
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/26:00 am
ORD
- POP
2 stops29h 47m
JetBlue
sáb. 5/93:12 pm
POP
- ORD
1 stop17h 29m
JetBlue
Deal found 3/12![JetBlue logo]()
$635
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.
dom. 4/266:35 pm
MDW
- PUJ
2 stops17h 05m
Southwest
dom. 5/104:15 pm
PUJ
- MDW
1 stop8h 25m
Southwest
Deal found 3/12![Southwest logo]()
$580
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.
mié. 4/1510:41 am
MDW
- STI
2 stops12h 41m
Delta
mié. 4/226:00 am
STI
- MDW
2 stops11h 26m
Delta
Deal found 3/14![Delta logo]()
$493
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.
vie. 5/89:30 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
mié. 5/131:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Deal found 3/12![United Airlines logo]()
$571
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/165:00 am
ORD
- POP
1 stop8h 30m
American Airlines
mié. 5/203:30 pm
POP
- ORD
1 stop8h 27m
American Airlines
Deal found 3/12![American Airlines logo]()
$631
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/13:21 pm
ORD
- POP
1 stop19h 12m
Copa Airlines
dom. 6/712:40 pm
POP
- ORD
1 stop16h 20m
Copa Airlines
Deal found 3/12![Copa Airlines logo]()
$539
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/181:11 pm
ORD
- STI
1 stop10h 11m
Delta
mar. 4/286:00 am
STI
- ORD
2 stops17h 21m
Delta
Deal found 3/15![Delta logo]()
$493
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.
lun. 4/135:00 am
ORD
- SDQ
1 stop8h 10m
United Airlines
vie. 4/173:20 pm
SDQ
- ORD
1 stop9h 17m
United Airlines
Deal found 3/12![United Airlines logo]()
$571
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.
dom. 4/265:15 am
MDW
- PUJ
1 stop9h 00m
Southwest
dom. 5/34:15 pm
PUJ
- MDW
1 stop8h 25m
Southwest
Deal found 3/12![Southwest logo]()
$629
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.
mié. 4/1511:19 am
ORD
- STI
2 stops12h 03m
Delta
mié. 4/226:00 am
STI
- ORD
2 stops11h 42m
Delta
Deal found 3/14![Delta logo]()
$493
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated marzo 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated marzo 17, 2026 and is based on user searches.
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.
jue. 4/24:51 pm
ORD
- SDQ
1 stop20h 05m
Multiple Airlines
mié. 4/83:01 pm
SDQ
- ORD
1 stop24h 41m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$322
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/1112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
sáb. 4/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/12![Arajet logo]()
$292
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/1112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/13![Arajet logo]()
$296
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/127:00 am
ORD
- PUJ
Nonstop4h 46m
Multiple Airlines
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$306
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.
lun. 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/16![Arajet logo]()
$293
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
sáb. 4/187:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/14![Arajet logo]()
$308
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/176:04 pm
ORD
- PUJ
1 stop14h 53m
Multiple Airlines
sáb. 4/257:02 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$300
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.
vie. 4/176:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$311
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.
sáb. 4/1812:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$303
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.
sáb. 4/2512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
jue. 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/15![Arajet logo]()
$302
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.
lun. 4/274:30 am
ORD
- SDQ
1 stop11h 25m
Multiple Airlines
jue. 4/303:30 pm
SDQ
- ORD
1 stop9h 10m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$303
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/274:30 am
ORD
- PUJ
Nonstop4h 45m
Multiple Airlines
lun. 5/49:13 pm
PUJ
- ORD
2 stops27h 00m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$307
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 marzo 17, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated marzo 17, 2026.
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.
sáb. 8/2912:12 pm
ORD
- SDQ
1 stop8h 28m
Arajet
Deal found 3/16![Arajet logo]()
$121
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2912:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$122
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.
mar. 4/217:30 am
MDW
- SDQ
1 stop20h 59m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$129
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/126:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/13![Arajet logo]()
$131
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.
lun. 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/13![Arajet logo]()
$135
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/127:00 am
ORD
- PUJ
Nonstop4h 46m
Frontier
Deal found 3/13![Frontier logo]()
$137
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.
mar. 4/74:51 pm
ORD
- SDQ
1 stop20h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$139
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.
vie. 5/16:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/15![Arajet logo]()
$140
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.
jue. 4/24:51 pm
ORD
- SDQ
1 stop20h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$142
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.
sáb. 4/1112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 3/13![Arajet logo]()
$143
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.
mar. 3/314:51 pm
ORD
- SDQ
1 stop20h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$143
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/35:05 am
ORD
- SDQ
1 stop7h 10m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$146
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 marzo 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $292 (Booking.com) |
One-way from | $121 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $601 |
Good round-trip deal | $420 or less |
Good one-way deal | $177 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 marzo 17, 2026.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
mié. 4/8
7:17 am-2:23 pm
1 stop6h 06m
Santiago de los Caballeros
vie. 4/10
2:46 am-11:17 am
1 stop9h 31m
$390
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
vie. 4/3
3:05 pm-10:54 am
1 stop18h 49m
Santo Domingo Las Americas
lun. 4/13
12:38 pm-1:13 am
1 stop13h 35m
$419
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
mar. 4/14
8:06 am-10:47 pm
1 stop13h 41m
Santo Domingo Las Americas
mié. 4/29
8:43 am-1:13 am
1 stop17h 30m
$419
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
lun. 4/6
3:05 pm-2:20 am
1 stop10h 15m
Santo Domingo Las Americas
lun. 4/13
12:08 pm-1:13 am
1 stop14h 05m
$419
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
mar. 5/19
3:21 pm-11:42 am
1 stop19h 21m
Santo Domingo Las Americas
dom. 5/24
8:45 am-1:15 am
1 stop17h 30m
$419
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
lun. 4/27
8:50 pm-12:23 pm
2 stops14h 33m
Santiago de los Caballeros
lun. 5/4
1:32 pm-7:29 am
2 stops18h 57m
$473
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
mar. 5/26
7:00 am-12:59 am
2 stops16h 59m
Santiago de los Caballeros
jue. 6/11
6:15 am-4:36 pm
2 stops11h 21m
$476
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
lun. 4/27
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
jue. 4/30
2:46 pm-10:28 pm
1 stop8h 42m
$479
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
vie. 4/17
6:00 am-1:12 pm
1 stop6h 12m
Santo Domingo Las Americas
sáb. 4/25
2:37 pm-10:28 pm
1 stop8h 51m
$479
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
sáb. 5/23
5:05 am-2:02 pm
1 stop7h 57m
Santiago de los Caballeros
dom. 5/31
3:07 pm-12:27 am
1 stop10h 20m
$483
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-PUJ
ORD-SDQ
ORD-STI
MDW-SDQ
MDW-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Dominican Republic
CHI-DO0
ORD-PUJ
ORD-SDQ
ORD-STI
MDW-SDQ
What is the cheapest month to book a flight from Chicago to Dominican Republic?
Currently, December is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $195). Flying from Chicago to Dominican Republic in October is currently the most expensive (average of $289). 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 marzo 17, 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 marzo 17, 2026.
The most flights from CHI to DO0 are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (5 on average).
How often are flights from Chicago to the Dominican Republic delayed?
About 18% 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 at night are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday 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 16% 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 marzo 17, 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
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Dominican Republic. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Dominican Republic
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Dominican Republic by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Dominican Republic by cabin class
Find flights from Chicago to Dominican Republic, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Dominican Republic flights
Browse other Chicago and Dominican Republic flight options. Last updated on marzo 17, 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 marzo 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$398 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$188 | Average$458 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$191 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$511 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$221 | Average$433 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$245 | Average$527 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$491 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$274 | Average$569 | FlexibilityNo cancel fee | On-time71% |