$155+ 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
Sep 7 — Sep 141
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Dominican Republic with Cheapflights
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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 August 8, 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 August 8, 2026.
This Arajet deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
1 stop8h 35m
Fri 11/131:40 am -
1 stop9h 17m
Deal found 8/4![Multiple Airlines logo]()
$341
This Arajet deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop8h 28m
Fri 9/181:40 am -
1 stop10h 32m
Deal found 8/4![Multiple Airlines logo]()
$371
This FlightHub deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Sat 10/243:40 pm -
1 stop25h 05m
Sun 11/16:10 pm -
Nonstop5h 10m
Deal found 8/7![Multiple Airlines logo]()
$375
This Orbitz deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Wed 10/284:30 pm -
2 stops19h 15m
Sun 11/16:10 pm -
Nonstop5h 10m
Deal found 8/7![Multiple Airlines logo]()
$376
This Gotogate deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:05 am -
1 stop14h 30m
Sun 11/86:10 pm -
Nonstop5h 10m
Deal found 8/7![Multiple Airlines logo]()
$377
This Travelocity deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Sat 8/2912:12 pm -
Nonstop4h 45m
Wed 9/25:05 pm -
1 stop22h 50m
Deal found 8/7![Multiple Airlines logo]()
$379
This Arajet deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/1712:12 pm -
1 stop8h 28m
Sun 10/251:55 pm -
1 stop9h 15m
Deal found 8/8![Multiple Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 8/285:49 pm -
1 stop17h 12m
Thu 9/33:05 pm -
Nonstop5h 20m
Deal found 8/7![American Airlines logo]()
$380
This Expedia deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:40 pm -
1 stop25h 05m
Mon 11/23:15 pm -
1 stop25h 37m
Deal found 8/7![Air Canada logo]()
$381
This Arajet deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/1912:12 pm -
1 stop8h 28m
Fri 9/251:40 am -
1 stop10h 32m
Deal found 8/8![Multiple Airlines logo]()
$381
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/253:45 pm -
1 stop25h 00m
Sun 11/17:45 pm -
1 stop17h 22m
Deal found 8/7![Air Canada logo]()
$382
This Orbitz deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 am -
Nonstop4h 45m
Tue 10/272:15 pm -
1 stop21h 52m
Deal found 8/4![Multiple Airlines logo]()
$383
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 August 8, 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 August 8, 2026.
This Arajet deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/1212:12 pm -
1 stop8h 28m
Fri 9/181:40 am -
1 stop10h 32m
Deal found 8/6![Multiple Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/135:00 am -
1 stop9h 30m
Wed 9/163:35 pm -
1 stop9h 05m
Deal found 8/7![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/15:30 am -
1 stop9h 12m
Mon 2/86:06 pm -
1 stop7h 44m
Deal found 8/5![Delta logo]()
$390
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/105:00 am -
1 stop9h 08m
Wed 12/97:00 am -
1 stop14h 56m
Deal found 8/8![American Airlines logo]()
$428
This Arajet deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm -
Nonstop4h 45m
Sat 8/297:02 am -
Nonstop5h 10m
Deal found 8/4![Arajet logo]()
$455
This Copa Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 stop10h 05m
Sat 10/312:25 pm -
1 stop11h 46m
Deal found 8/6![Copa Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:00 am -
1 stop7h 55m
Wed 9/161:45 pm -
1 stop8h 15m
Deal found 8/7![Southwest logo]()
$568
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 1/305:30 am -
1 stop9h 12m
Sat 2/66:06 pm -
1 stop7h 44m
Deal found 8/6![Delta logo]()
$390
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am -
1 stop7h 27m
Sat 9/266:45 pm -
1 stop13h 57m
Deal found 8/5![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/196:00 pm -
1 stop17h 42m
Thu 10/14:00 pm -
2 stops16h 56m
Deal found 8/8![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:56 am -
2 stops9h 07m
Wed 9/93:15 pm -
1 stop10h 18m
Deal found 8/3![American Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/189:23 am -
Nonstop4h 37m
Sun 10/251:55 pm -
Nonstop5h 15m
Deal found 8/8![United Airlines logo]()
$444
This Copa Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 stop20h 57m
Sun 11/158:55 am -
1 stop17h 16m
Deal found 8/6![Copa Airlines logo]()
$492
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/108:59 pm -
1 stop14h 36m
Mon 10/121:35 pm -
1 stop9h 55m
Deal found 8/8![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/107:00 am -
2 stops10h 35m
Wed 12/96:40 am -
2 stops11h 44m
Deal found 8/8![Delta logo]()
$445
This Copa Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:20 pm -
1 stop10h 05m
Sun 9/136:06 am -
1 stop19h 56m
Deal found 8/4![Copa Airlines logo]()
$492
This Copa Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Sun 9/63:20 pm -
1 stop19h 22m
Sun 9/136:06 am -
1 stop19h 56m
Deal found 8/7![Copa Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/257:38 am -
Nonstop4h 37m
Thu 10/291:55 pm -
Nonstop5h 15m
Deal found 8/7![United Airlines logo]()
$495
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:55 pm -
2 stops16h 30m
Thu 9/171:45 pm -
1 stop10h 00m
Deal found 8/5![Southwest logo]()
$608
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop7h 15m
Sat 10/33:15 pm -
1 stop7h 25m
Deal found 8/4![American Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/196:00 pm -
1 stop17h 42m
Tue 9/292:08 pm -
2 stops23h 33m
Deal found 8/8![Delta logo]()
$465
This Copa Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:20 pm -
1 stop23h 55m
Wed 9/98:47 am -
1 stop17h 15m
Deal found 8/3![Copa Airlines logo]()
$492
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 12/58:59 pm -
1 stop14h 23m
Tue 12/157:00 am -
2 stops11h 05m
Deal found 8/6![American Airlines logo]()
$526
This Copa Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm -
1 stop22h 38m
Sat 10/174:10 pm -
1 stop9h 47m
Deal found 8/4![Copa Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:05 am -
1 stop6h 22m
Sat 9/192:53 pm -
1 stop8h 51m
Deal found 8/4![Delta logo]()
$520
This Copa Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:01 am -
1 stop26h 41m
Tue 9/1512:12 pm -
1 stop26h 47m
Deal found 8/5![Copa Airlines logo]()
$505
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:40 pm -
2 stops16h 30m
Mon 11/94:50 pm -
1 stop8h 05m
Deal found 8/4![Southwest logo]()
$761
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/106:00 am -
1 stop16h 30m
Fri 1/228:45 pm -
1 stop14h 39m
Deal found 8/3![Delta logo]()
$520
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 1/246:15 pm -
1 stop16h 53m
Fri 1/292:15 pm -
1 stop9h 32m
Deal found 8/8![United Airlines logo]()
$678
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/291:00 pm -
2 stops9h 30m
Fri 2/57:30 am -
2 stops13h 07m
Deal found 8/8![Delta logo]()
$525
Last-minute flights from Chicago to Dominican RepublicDiscover last-minute flight deals from Chicago to Dominican Republic. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Dominican Republic. Data last updated August 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:49 pm -
1 stop17h 12m
Thu 9/33:05 pm -
Nonstop5h 20m
Deal found 8/5![American Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:49 pm -
1 stop17h 12m
Wed 9/24:14 pm -
1 stop16h 16m
Deal found 8/4![American Airlines logo]()
$390
This Travelocity deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Sat 8/2912:12 pm -
Nonstop4h 45m
Wed 9/25:05 pm -
1 stop22h 50m
Deal found 8/7![Multiple Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/296:49 am -
1 stop7h 17m
Sat 9/512:10 pm -
1 stop8h 36m
Deal found 8/6![American Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:23 am -
Nonstop4h 37m
Sat 9/52:20 pm -
1 stop11h 39m
Deal found 8/4![United Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:30 am -
Nonstop4h 45m
Sat 9/57:02 am -
Nonstop5h 10m
Deal found 8/4![Arajet logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:30 am -
Nonstop4h 45m
Thu 9/37:30 pm -
Nonstop5h 10m
Deal found 8/5![Arajet logo]()
$385
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop10h 00m
Deal found 8/4![Southwest logo]()
$390
This Expedia deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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.
Sun 9/67:25 am -
2 stops31h 40m
Sat 9/267:02 am -
Nonstop5h 10m
Deal found 8/8![Multiple Airlines logo]()
$392
This Arajet deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm -
1 stop8h 28m
Fri 9/181:40 am -
1 stop10h 32m
Deal found 8/4![Multiple Airlines logo]()
$371
This Arajet deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 am -
Nonstop4h 45m
Sun 9/206:00 pm -
Nonstop5h 10m
Deal found 8/7![Arajet logo]()
$375
This Arajet deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/1912:12 pm -
1 stop8h 28m
Fri 9/251:40 am -
1 stop10h 32m
Deal found 8/8![Multiple Airlines logo]()
$381
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 August 8, 2026.
Search for one-way flight options from Chicago to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This Arajet deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/2912:12 pm -
1 stop8h 28m
Deal found 8/8![Multiple Airlines logo]()
$155
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:41 am -
1 stop7h 40m
Deal found 8/4![American Airlines logo]()
$163
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Mon 9/75:30 am -
Nonstop4h 45m
Deal found 8/7![Arajet logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
1 stop17h 35m
Deal found 8/4![Frontier logo]()
$167
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:45 am -
Nonstop4h 45m
Deal found 8/5![Arajet logo]()
$168
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:45 am -
Nonstop4h 45m
Deal found 8/7![Arajet logo]()
$169
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/156:59 pm -
1 stop16h 48m
Deal found 8/8![American Airlines logo]()
$173
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:21 am -
Nonstop4h 44m
Deal found 8/4![American Airlines logo]()
$174
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:20 am -
2 stops8h 42m
Deal found 8/4![American Airlines logo]()
$178
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/34:30 pm -
2 stops19h 12m
Deal found 8/7![Delta logo]()
$178
This Arajet deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/1012:12 pm -
Nonstop4h 45m
Deal found 8/7![Arajet logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:01 pm -
2 stops12h 57m
Deal found 8/5![American Airlines logo]()
$180
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 August 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (Arajet) |
One-way from | $155 (Arajet) |
Popular in | June |
Cheapest in | September |
Average price | $544 |
Good round-trip deal | $522 or less |
Good one-way deal | $217 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 August 8, 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
Sat 9/12
12:12 pm-9:40 pm
1 stop8h 28m
Santo Domingo Las Americas
Fri 9/18
1:40 am-11:12 am
1 stop10h 32m
$389
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 9/13
5:00 am-3:30 pm
1 stop9h 30m
Punta Cana
Wed 9/16
3:35 pm-11:40 pm
1 stop9h 05m
$390
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 2/1
5:30 am-4:42 pm
1 stop9h 12m
Punta Cana
Mon 2/8
6:06 pm-11:50 pm
1 stop7h 44m
$390
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 1/30
5:30 am-4:42 pm
1 stop9h 12m
Punta Cana
Sat 2/6
6:06 pm-11:50 pm
1 stop7h 44m
$390
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 9/19
6:00 pm-12:42 pm
1 stop17h 42m
Punta Cana
Thu 10/1
4:00 pm-7:56 am
2 stops16h 56m
$395
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 9/12
6:00 am-2:27 pm
1 stop7h 27m
Punta Cana
Sat 9/26
6:45 pm-7:42 am
1 stop13h 57m
$414
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Tue 11/10
5:00 am-4:08 pm
1 stop9h 08m
Santiago de los Caballeros
Wed 12/9
7:00 am-7:56 pm
1 stop14h 56m
$428
Quickest round-trip
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 10/18
9:23 am-3:00 pm
Nonstop4h 37m
Punta Cana
Sun 10/25
1:55 pm-6:10 pm
Nonstop5h 15m
$444
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Tue 11/10
7:00 am-7:35 pm
2 stops10h 35m
Santiago de los Caballeros
Wed 12/9
6:40 am-4:24 pm
2 stops11h 44m
$445
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 8/22
12:12 pm-5:57 pm
Nonstop4h 45m
Punta Cana
Sat 8/29
7:02 am-11:12 am
Nonstop5h 10m
$455
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Dominican Republic
Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Chicago with our price prediction graph.
ORD-SDQ
ORD-PUJ
MDW-PUJ
ORD-STI
MDW-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to the Dominican Republic
CHI-DO0
ORD-SDQ
ORD-PUJ
MDW-PUJ
ORD-STI
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 $436). Flying from Chicago to Dominican Republic in June is currently the most expensive (average of $681). 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 August 8, 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 August 8, 2026.
The most flights from CHI to DO0 are scheduled on a Friday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
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 140 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 18% 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 19 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 August 8, 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.
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 August 8, 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 August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$222 | Average$372 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$223 | Average$755 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$231 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$517 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$239 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$445 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$349 | Average$622 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$383 | Average$605 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$503 | Average$816 | FlexibilityNo cancel fee | On-time63% |