$183+ Cheap flights from the Dominican Republic to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Sep 4 — Sep 111
Round-trip
1 adult, Economy
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Find cheap flights from Dominican Republic to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Dominican Republic to ChicagoExplore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
Explore the most affordable flight options available from Dominican Republic to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/215:47 am -
Nonstop5h 10m
Sun 12/63:20 am -
Nonstop4h 45m
Deal found 7/31![Arajet logo]()
$300
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 pm -
Nonstop5h 10m
Fri 9/256:45 am -
Nonstop4h 45m
Deal found 8/3![Arajet logo]()
$301
This Booking.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/57:02 am -
Nonstop5h 10m
Fri 9/116:45 am -
Nonstop4h 45m
Deal found 7/31![Arajet logo]()
$302
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.
Sat 10/315:47 am -
Nonstop5h 10m
Sat 11/710:27 am -
Nonstop4h 45m
Deal found 8/4![Arajet logo]()
$321
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 9/181:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/4![Multiple Airlines logo]()
$327
This Arajet deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/1![Multiple Airlines logo]()
$332
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 pm -
Nonstop5h 10m
Mon 9/285:30 am -
Nonstop4h 45m
Deal found 8/3![Arajet logo]()
$338
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:45 pm -
1 stop10h 55m
Mon 9/215:30 am -
1 stop10h 25m
Deal found 8/3![Multiple Airlines logo]()
$353
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:30 pm -
Nonstop5h 10m
Mon 9/145:30 am -
Nonstop4h 45m
Deal found 8/2![Arajet logo]()
$354
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:02 am -
Nonstop5h 10m
Sat 9/1912:12 pm -
Nonstop4h 45m
Deal found 8/2![Arajet logo]()
$359
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 pm -
Nonstop5h 10m
Thu 9/243:40 pm -
1 stop23h 25m
Deal found 8/3![Multiple Airlines logo]()
$373
This Arajet deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:45 pm -
1 stop10h 55m
Mon 9/145:30 am -
1 stop10h 25m
Deal found 8/2![Multiple Airlines logo]()
$396
Best flights from Dominican Republic to ChicagoDiscover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
Discover carefully curated flight deals from Dominican Republic to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/3![Multiple Airlines logo]()
$327
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 10/315:47 am -
Nonstop5h 10m
Sat 11/710:27 am -
Nonstop4h 45m
Deal found 8/4![Arajet logo]()
$403
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
Nonstop5h 15m
Sun 11/15:30 am -
1 stop8h 34m
Deal found 8/1![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/194:45 pm -
1 stop7h 25m
Mon 1/46:00 am -
1 stop7h 30m
Deal found 8/1![Delta logo]()
$486
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 9/212:42 pm -
1 stop13h 20m
Sat 9/53:20 pm -
1 stop10h 05m
Deal found 8/3![Copa Airlines logo]()
$521
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/1810:21 am -
2 stops13h 10m
Sun 9/205:18 am -
2 stops8h 59m
Deal found 7/31![American Airlines logo]()
$543
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/194:10 pm -
Nonstop5h 05m
Mon 1/45:05 am -
1 stop6h 40m
Deal found 8/1![Southwest logo]()
$556
This JetBlue deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:01 am -
1 stop9h 19m
Sat 11/142:15 pm -
1 stop9h 36m
Deal found 8/1![JetBlue logo]()
$621
This Arajet deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/1![Multiple Airlines logo]()
$332
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:29 pm -
2 stops39h 21m
Fri 8/2811:50 am -
1 stop25h 37m
Deal found 8/4![Frontier logo]()
$715
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:50 pm -
1 stop10h 31m
Mon 9/289:52 pm -
1 stop13h 48m
Deal found 8/3![United Airlines logo]()
$422
This Booking.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:02 am -
Nonstop5h 10m
Sat 10/36:21 pm -
2 stops19h 59m
Deal found 8/2![Multiple Airlines logo]()
$388
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 9/1612:42 pm -
1 stop13h 20m
Wed 9/233:20 pm -
1 stop19h 22m
Deal found 8/3![Copa Airlines logo]()
$521
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.
Mon 9/142:53 pm -
1 stop10h 06m
Wed 9/165:30 am -
1 stop6h 57m
Deal found 8/4![Delta logo]()
$566
This Copa Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:06 pm -
1 stop19h 40m
Mon 11/302:13 pm -
1 stop9h 55m
Deal found 8/2![Copa Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop16h 32m
Sat 10/247:52 pm -
1 stop25h 54m
Deal found 8/2![United Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:12 pm -
1 stop9h 21m
Tue 10/135:05 am -
1 stop8h 07m
Deal found 8/2![American Airlines logo]()
$611
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:15 pm -
1 stop7h 35m
Tue 9/226:15 am -
1 stop6h 05m
Deal found 8/1![Southwest logo]()
$632
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:00 am -
1 stop18h 21m
Tue 10/206:00 pm -
1 stop16h 55m
Deal found 8/2![United Airlines logo]()
$538
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:49 pm -
1 stop8h 19m
Wed 9/166:00 am -
1 stop6h 27m
Deal found 7/31![JetBlue logo]()
$653
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.
Thu 11/53:57 pm -
1 stop8h 36m
Mon 11/96:00 am -
1 stop6h 40m
Deal found 8/5![Delta logo]()
$604
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:45 pm -
1 stop7h 35m
Mon 10/195:00 am -
1 stop6h 25m
Deal found 8/2![Southwest logo]()
$638
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/142:53 pm -
1 stop8h 51m
Mon 9/216:05 am -
1 stop6h 22m
Deal found 7/31![Delta logo]()
$604
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 9/192:53 pm -
1 stop8h 51m
Mon 9/286:05 am -
1 stop6h 22m
Deal found 8/4![Delta logo]()
$628
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:07 pm -
1 stop11h 21m
Wed 9/237:05 am -
1 stop14h 47m
Deal found 8/3![United Airlines logo]()
$629
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Thu 9/177:35 pm -
2 stops16h 25m
Fri 9/253:20 pm -
1 stop21h 05m
Deal found 7/31![Multiple Airlines logo]()
$704
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:45 pm -
1 stop10h 00m
Mon 9/147:55 pm -
2 stops16h 25m
Deal found 8/2![Southwest logo]()
$725
This United Airlines deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop28h 13m
Mon 9/219:35 pm -
1 stop24h 17m
Deal found 8/1![United Airlines logo]()
$632
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:45 pm -
1 stop7h 25m
Fri 1/16:00 am -
1 stop9h 05m
Deal found 7/31![Delta logo]()
$657
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:30 pm -
2 stops22h 07m
Mon 9/216:00 am -
1 stop10h 59m
Deal found 8/1![Delta logo]()
$697
Last-minute flights from Dominican Republic to ChicagoDiscover last-minute flight deals from Dominican Republic to Chicago. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Dominican Republic to Chicago. Data last updated August 5, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:02 am -
Nonstop5h 10m
Fri 9/116:45 am -
Nonstop4h 45m
Deal found 8/1![Arajet logo]()
$308
This Mytrip deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:02 am -
Nonstop5h 10m
Fri 9/113:40 pm -
1 stop23h 25m
Deal found 8/2![Multiple Airlines logo]()
$381
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:30 pm -
Nonstop5h 10m
Mon 9/145:30 am -
Nonstop4h 45m
Deal found 8/2![Arajet logo]()
$354
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:02 am -
Nonstop5h 10m
Sat 9/1912:12 pm -
Nonstop4h 45m
Deal found 8/2![Arajet logo]()
$359
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 pm -
Nonstop5h 10m
Fri 9/256:45 am -
Nonstop4h 45m
Deal found 8/3![Arajet logo]()
$301
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:45 pm -
1 stop10h 55m
Mon 9/215:30 am -
1 stop10h 25m
Deal found 8/3![Multiple Airlines logo]()
$353
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 pm -
Nonstop5h 10m
Thu 9/243:40 pm -
1 stop23h 25m
Deal found 8/3![Multiple Airlines logo]()
$373
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 pm -
Nonstop5h 10m
Fri 9/253:40 pm -
1 stop23h 25m
Deal found 8/3![Multiple Airlines logo]()
$383
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 9/181:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/4![Multiple Airlines logo]()
$327
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 pm -
Nonstop5h 10m
Mon 9/285:30 am -
Nonstop4h 45m
Deal found 8/3![Arajet logo]()
$338
This Travelocity deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:30 pm -
Nonstop5h 10m
Sat 10/32:00 pm -
2 stops25h 05m
Deal found 8/2![Multiple Airlines logo]()
$379
This Arajet deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:40 am -
1 stop10h 32m
Mon 9/285:30 am -
1 stop10h 25m
Deal found 8/1![Multiple Airlines logo]()
$332
One-way flights from Dominican Republic to ChicagoSearch for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
Search for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:40 am -
1 stop9h 17m
Deal found 8/3![Multiple Airlines logo]()
$183
This Arajet deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/251:40 am -
1 stop10h 32m
Deal found 7/31![Multiple Airlines logo]()
$188
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 2/16:06 pm -
1 stop17h 46m
Deal found 8/5![Delta logo]()
$226
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.
Fri 9/43:35 pm -
1 stop28h 02m
Deal found 8/5![United Airlines logo]()
$226
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.
Wed 9/24:04 pm -
2 stops22h 04m
Deal found 8/4![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 1/296:06 pm -
2 stops20h 27m
Deal found 7/31![Delta logo]()
$228
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.
Wed 9/303:35 pm -
1 stop8h 57m
Deal found 8/5![United Airlines logo]()
$228
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.
Thu 10/14:00 pm -
2 stops16h 56m
Deal found 8/4![Delta logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:43 pm -
2 stops25h 41m
Deal found 8/1![Frontier logo]()
$231
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.
Thu 10/14:00 pm -
2 stops18h 07m
Deal found 8/4![Delta logo]()
$232
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.
Fri 10/22:08 pm -
2 stops25h 21m
Deal found 8/5![Delta logo]()
$232
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.
Tue 11/33:05 pm -
2 stops26h 12m
Deal found 8/3![Delta logo]()
$234
Find flight deals from Dominican Republic to Chicago
Keep the following information in mind while searching for Dominican Republic to Chicago flight deals. Data was last updated August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Booking.com) |
One-way from | $183 (Arajet) |
Popular in | June |
Cheapest in | December |
Average price | $425 |
Good round-trip deal | $484 or less |
Good one-way deal | $267 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Dominican Republic to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 5, 2026.
Use the filters below to find and compare flights from the Dominican Republic to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 9/18
1:40 am-11:12 am
1 stop10h 32m
Chicago O'Hare Intl
Mon 9/28
5:30 am-4:55 pm
1 stop10h 25m
$327
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 9/25
1:40 am-11:12 am
1 stop10h 32m
Chicago O'Hare Intl
Mon 9/28
5:30 am-4:55 pm
1 stop10h 25m
$332
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 9/19
7:02 am-11:12 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 10/3
6:21 pm-3:20 pm
2 stops19h 59m
$388
Quickest round-trip
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 10/31
5:47 am-9:57 am
Nonstop5h 10m
Chicago O'Hare Intl
Sat 11/7
10:27 am-5:12 pm
Nonstop4h 45m
$403
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 10/29
1:55 pm-6:10 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sun 11/1
5:30 am-4:04 pm
1 stop8h 34m
$412
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Thu 9/24
1:50 pm-11:21 pm
1 stop10h 31m
Chicago O'Hare Intl
Mon 9/28
9:52 pm-12:40 pm
1 stop13h 48m
$422
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Sat 12/19
4:45 pm-10:10 pm
1 stop7h 25m
Chicago Midway
Mon 1/4
6:00 am-3:30 pm
1 stop7h 30m
$486
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Wed 9/2
12:42 pm-1:02 am
1 stop13h 20m
Chicago O'Hare Intl
Sat 9/5
3:20 pm-2:25 am
1 stop10h 05m
$521
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Wed 9/16
12:42 pm-1:02 am
1 stop13h 20m
Chicago O'Hare Intl
Wed 9/23
3:20 pm-11:42 am
1 stop19h 22m
$521
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Tue 11/24
7:06 pm-12:46 pm
1 stop19h 40m
Chicago O'Hare Intl
Mon 11/30
2:13 pm-2:08 am
1 stop9h 55m
$521
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Dominican Republic to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
SDQ-ORD
PUJ-ORD
PUJ-MDW
SDQ-MDW
STI-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from the Dominican Republic to Chicago
DO0-CHI
SDQ-ORD
PUJ-ORD
PUJ-MDW
SDQ-MDW
What is the cheapest month to book a flight from Dominican Republic to Chicago?
Currently, February is the cheapest month in which you can book a flight from Dominican Republic to Chicago (average of $375). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $801). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from DO to CHI?
Find hourly flight availability from Dominican Republic to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 5, 2026.
It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Dominican Republic to Chicago
Explore weekly flight availability from Dominican Republic to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 5, 2026.
The most flights from DO0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 5, 2026.
Peruse reviews from past customers who have flown with American Airlines from the Dominican Republic to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Boarding
7.5
Comfort
7.2
Entertainment
6.8
Food
6.4
Overall
7.1
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Crew
7.9
Boarding
7.5
Comfort
7.2
Entertainment
6.8
Food
6.4
Overall
7.1
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Dominican Republic to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Dominican Republic to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Dominican Republic to Chicago by cabin class
Find flights from Dominican Republic to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Dominican Republic and Chicago flights
Browse other Dominican Republic and Chicago flight options. Last updated on August 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Dominican Republic to Chicago
Discover the top 3 airlines that operate flights from Dominican Republic to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$237 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$515 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$375 | Average$411 | FlexibilityNo cancel fee | On-time62% |