$154+ Cheap flights from Chicago (CHI) to the Dominican Republic
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Oct 21 — Oct 281
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Dominican Republic with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 September 21, 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 September 21, 2026.
This Booking.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 11/1411:10 am -
Nonstop4h 45m
Sat 11/217:00 am -
Nonstop5h 10m
Deal found 9/18![Arajet logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:55 pm -
1 stop12h 44m
Fri 10/234:12 pm -
1 stop17h 48m
Deal found 9/21![American Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/166:45 am -
Nonstop4h 45m
Sun 10/186:00 pm -
Nonstop5h 10m
Deal found 9/18![Arajet logo]()
$363
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:45 am -
Nonstop4h 45m
Sat 12/57:00 am -
Nonstop5h 10m
Deal found 9/17![Arajet logo]()
$364
This Arajet deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/711:10 am -
1 stop8h 30m
Fri 11/201:40 am -
1 stop10h 30m
Deal found 9/20![Multiple Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:29 pm -
1 stop16h 06m
Sun 11/15:33 pm -
1 stop7h 57m
Deal found 9/21![American Airlines logo]()
$365
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:20 am -
Nonstop4h 45m
Sat 11/77:00 am -
Nonstop5h 10m
Deal found 9/17![Arajet logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:20 am -
Nonstop4h 45m
Thu 11/197:30 pm -
Nonstop5h 10m
Deal found 9/19![Arajet logo]()
$369
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 am -
Nonstop4h 45m
Sat 10/317:00 am -
Nonstop5h 10m
Deal found 9/16![Arajet logo]()
$375
This Arajet deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/711:10 am -
1 stop8h 30m
Fri 11/131:40 am -
1 stop10h 30m
Deal found 9/20![Multiple Airlines logo]()
$375
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:55 pm -
2 stops26h 50m
Thu 12/177:30 pm -
Nonstop5h 10m
Deal found 9/16![Multiple Airlines logo]()
$377
This Arajet deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/1411:10 am -
1 stop8h 30m
Fri 11/201:40 am -
1 stop10h 30m
Deal found 9/18![Multiple Airlines logo]()
$390
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 September 21, 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 September 21, 2026.
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Mon 11/169:17 am -
Nonstop4h 40m
Fri 11/202:55 pm -
Nonstop5h 15m
Deal found 9/21![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:10 am -
1 stop10h 23m
Tue 11/109:25 pm -
1 stop14h 02m
Deal found 9/20![Delta logo]()
$430
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Tue 11/106:29 am -
1 stop6h 47m
Wed 12/95:08 pm -
2 stops16h 52m
Deal found 9/21![American Airlines logo]()
$431
This JetBlue deal was found by Cheapflights users on 9/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 am -
1 stop6h 13m
Sun 11/84:33 pm -
1 stop9h 22m
Deal found 9/17![JetBlue logo]()
$476
This Copa Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:20 pm -
1 stop18h 34m
Sat 10/317:07 pm -
1 stop19h 39m
Deal found 9/21![Copa Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:05 am -
1 stop8h 05m
Fri 12/42:40 pm -
1 stop8h 35m
Deal found 9/16![Southwest logo]()
$565
This Mytrip deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Thu 10/294:30 pm -
1 stop17h 50m
Mon 11/21:50 pm -
1 stop8h 08m
Deal found 9/18![Multiple Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
1 stop8h 04m
Sun 11/15:10 pm -
1 stop8h 51m
Deal found 9/19![United Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/97:15 pm -
2 stops15h 13m
Sat 11/143:45 pm -
2 stops18h 04m
Deal found 9/21![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sat 10/318:42 am -
Nonstop4h 37m
Tue 11/37:30 pm -
1 stop14h 17m
Deal found 9/21![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:04 am -
2 stops10h 29m
Tue 11/107:00 am -
2 stops11h 18m
Deal found 9/20![Delta logo]()
$435
This Copa Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/62:13 pm -
1 stop18h 48m
Fri 3/58:40 am -
1 stop17h 04m
Deal found 9/21![Copa Airlines logo]()
$483
This JetBlue deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop6h 58m
Fri 12/182:50 pm -
1 stop10h 59m
Deal found 9/19![JetBlue logo]()
$487
This Copa Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/17:35 am -
1 stop13h 21m
Fri 2/262:19 pm -
1 stop11h 52m
Deal found 9/21![Copa Airlines logo]()
$483
This JetBlue deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:30 pm -
1 stop9h 24m
Fri 11/276:35 am -
1 stop12h 05m
Deal found 9/21![JetBlue logo]()
$491
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 10/316:04 am -
1 stop6h 26m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 9/16![Delta logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 2/112:13 pm -
1 stop19h 29m
Sun 2/215:53 am -
1 stop20h 18m
Deal found 9/21![Copa Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:55 pm -
2 stops15h 50m
Mon 11/24:50 pm -
1 stop8h 05m
Deal found 9/19![Southwest logo]()
$595
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Mon 11/2312:59 pm -
1 stop8h 52m
Fri 11/274:00 pm -
1 stop10h 01m
Deal found 9/18![United Airlines logo]()
$495
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop6h 47m
Fri 10/233:57 pm -
1 stop8h 33m
Deal found 9/18![JetBlue logo]()
$498
This Copa Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:20 pm -
1 stop18h 34m
Mon 10/1912:42 pm -
1 stop13h 15m
Deal found 9/19![Copa Airlines logo]()
$489
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop7h 27m
Tue 10/134:40 pm -
1 stop17h 20m
Deal found 9/16![United Airlines logo]()
$497
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:55 pm -
1 stop10h 09m
Mon 10/125:01 am -
1 stop9h 49m
Deal found 9/18![JetBlue logo]()
$517
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:05 am -
1 stop14h 20m
Wed 12/167:00 am -
1 stop16h 36m
Deal found 9/20![Delta logo]()
$520
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/57:50 pm -
1 stop16h 35m
Tue 11/103:15 pm -
2 stops10h 46m
Deal found 9/21![American Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:45 pm -
2 stops16h 25m
Sun 12/64:05 pm -
1 stop9h 00m
Deal found 9/19![Southwest logo]()
$645
This Copa Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Fri 11/62:13 pm -
1 stop23h 59m
Sun 11/82:20 pm -
1 stop11h 51m
Deal found 9/18![Copa Airlines logo]()
$502
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/1811:27 am -
2 stops12h 47m
Thu 11/263:57 pm -
1 stop8h 57m
Deal found 9/19![Delta logo]()
$525
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 am -
1 stop8h 27m
Tue 10/63:35 pm -
1 stop8h 57m
Deal found 9/16![United Airlines logo]()
$527
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:00 pm -
2 stops14h 28m
Tue 11/103:15 pm -
2 stops10h 15m
Deal found 9/20![American Airlines logo]()
$705
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated September 21, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 9/268:50 am -
Nonstop4h 37m
Sat 10/31:50 pm -
Nonstop5h 04m
Deal found 9/18![United Airlines logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Mon 10/55:30 am -
Nonstop4h 45m
Sat 11/77:00 am -
Nonstop5h 10m
Deal found 9/17![Arajet logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/166:45 am -
Nonstop4h 45m
Sun 10/186:00 pm -
Nonstop5h 10m
Deal found 9/18![Arajet logo]()
$363
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:55 pm -
1 stop12h 44m
Fri 10/234:12 pm -
1 stop17h 48m
Deal found 9/21![American Airlines logo]()
$360
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:56 pm -
1 stop17h 49m
Sat 10/317:00 am -
Nonstop5h 10m
Deal found 9/16![Multiple Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sat 10/245:30 am -
1 stop9h 00m
Sat 10/313:25 pm -
Nonstop5h 16m
Deal found 9/21![United Airlines logo]()
$404
This Travelocity deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:55 pm -
2 stops21h 50m
Sun 11/112:35 pm -
1 stop9h 17m
Deal found 9/21![Air Canada logo]()
$407
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 am -
Nonstop4h 45m
Sat 10/317:00 am -
Nonstop5h 10m
Deal found 9/16![Arajet logo]()
$375
This Arajet deal was found by Cheapflights users on 9/17. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:20 am -
Nonstop4h 45m
Sun 11/17:10 pm -
Nonstop5h 10m
Deal found 9/17![Arajet logo]()
$395
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Tue 10/273:45 pm -
1 stop25h 00m
Tue 11/33:15 pm -
1 stop25h 37m
Deal found 9/18![Air Canada logo]()
$406
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:29 pm -
1 stop16h 06m
Sun 11/15:33 pm -
1 stop7h 57m
Deal found 9/21![American Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sat 10/317:38 am -
Nonstop4h 37m
Tue 11/1012:56 pm -
1 stop7h 58m
Deal found 9/21![United Airlines logo]()
$391
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 September 21, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:45 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Arajet logo]()
$154
This Booking.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 11/711:10 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Arajet logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Arajet logo]()
$156
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sat 10/317:38 am -
Nonstop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$159
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/1612:17 am -
1 stop15h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$160
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 11/25:19 am -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$163
This Booking.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Sun 12/64:20 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Arajet logo]()
$164
This Arajet deal was found by Cheapflights users on 9/17. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:20 am -
1 stop10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$168
This Arajet deal was found by Cheapflights users on 9/16. 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.
Sun 11/154:20 am -
1 stop10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/79:06 pm -
1 stop16h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$170
This Booking.com deal was found by Cheapflights users on 9/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
Nonstop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Arajet logo]()
$174
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:16 am -
2 stops14h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$177
Find flight deals from Chicago to Dominican Republic
Keep the following information in mind while searching for Chicago to Dominican Republic flight deals. Data was last updated September 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (CheapOair) |
One-way from | $154 (Expedia) |
Popular in | June |
Cheapest in | September |
Average price | $407 |
Good round-trip deal | $447 or less |
Good one-way deal | $208 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 7,457,451 searches. Data last updated September 21, 2026.
Use the filters below to find and compare flights from Chicago to the Dominican Republic that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Mon 1/11
12:17 am-5:20 pm
1 stop15h 03m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$184
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 11/16
7:00 am-3:26 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$194
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Sat 11/14
11:10 am-9:40 pm
1 stop8h 30m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$195
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Wed 10/28
1:00 pm-12:51 am
1 stop10h 51m
Santiago de los Caballeros
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$196
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 11/16
2:44 pm-12:28 pm
2 stops19h 44m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 11/17
5:30 am-3:30 pm
1 stop8h 00m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 11/15
7:00 am-3:26 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 11/14
2:44 pm-12:28 pm
2 stops19h 44m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 11/13
8:34 pm-2:20 pm
1 stop15h 46m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/16
5:13 pm-12:28 pm
1 stop17h 15m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
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-STI
ORD-SDQ
MDW-PUJ
ORD-POP
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Dominican Republic
CHI-DO0
ORD-PUJ
ORD-STI
ORD-SDQ
MDW-PUJ
What is the cheapest month to book a flight from Chicago to Dominican Republic?
Currently, September is the cheapest month in which you can book a flight from Chicago to Dominican Republic (average of $450). Flying from Chicago to Dominican Republic in June is currently the most expensive (average of $683). 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 September 21, 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.
How often are flights from Chicago to the Dominican Republic delayed?
About 22% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 146 minutes.
What is the most punctual flight time for Chicago to the Dominican Republic flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to the Dominican Republic flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Chicago to Dominican Republic?
The price you pay for your flight from Chicago to Dominican Republic may vary depending on when you book. For the best chance of a lower fare, look to book 17 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Dominican Republic
Get insights into the airlines that provide service to Dominican Republic. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Dominican Republic. Reviews last updated September 21, 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.
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - 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 September 21, 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 7,457,451 searches. Data last updated September 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$774 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$231 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$511 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$255 | Average$453 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$355 | Average$622 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$389 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$503 | Average$755 | FlexibilityNo cancel fee | On-time63% |