$202+ Cheap flights from the Dominican Republic to Chicago (CHI)
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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Dec 4 — Dec 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Dominican Republic to Chicago
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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 November 4, 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 November 4, 2026.
This eDestinos deal was found by Cheapflights users on 10/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:10 pm -
Nonstop5h 10m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$308
This eDestinos deal was found by Cheapflights users on 10/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:30 pm -
Nonstop5h 10m
Sat 11/2811:10 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$324
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
Nonstop5h 10m
Sun 1/34:20 am -
Nonstop4h 45m
Deal found 11/3![Arajet logo]()
$336
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/217:00 am -
Nonstop5h 10m
Sat 11/2811:10 am -
Nonstop4h 45m
Deal found 10/30![Arajet logo]()
$349
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
Nonstop5h 10m
Sat 1/211:10 am -
Nonstop4h 45m
Deal found 11/1![Arajet logo]()
$371
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/204:07 pm -
1 stop11h 26m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 10/31![Multiple Airlines logo]()
$379
This FlightHub deal was found by Cheapflights users on 11/4. 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 12/247:30 pm -
Nonstop5h 10m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 11/4![Arajet logo]()
$381
This Booking.com deal was found by Cheapflights users on 10/31. 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 12/267:00 am -
Nonstop5h 10m
Sat 1/211:10 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$387
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/131:27 pm -
1 stop8h 57m
Sun 1/1010:31 pm -
1 stop16h 49m
Deal found 11/4![Frontier logo]()
$397
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 12/204:49 pm -
1 stop7h 33m
Fri 1/16:00 am -
1 stop8h 49m
Deal found 10/31![Delta logo]()
$416
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 12/251:59 pm -
1 stop10h 23m
Mon 1/46:00 am -
1 stop6h 23m
Deal found 11/4![Delta logo]()
$439
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:25 pm -
1 stop28h 51m
Sun 1/108:30 pm -
1 stop14h 51m
Deal found 11/4![Frontier logo]()
$460
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 November 4, 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 November 4, 2026.
This Arajet deal was found by Cheapflights users on 11/3. 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.
Sat 2/67:00 am -
Nonstop5h 10m
Sun 2/74:20 am -
Nonstop4h 45m
Deal found 11/3![Arajet logo]()
$398
This Delta deal was found by Cheapflights users on 10/31. 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 1/146:13 pm -
1 stop7h 44m
Fri 1/295:30 am -
1 stop9h 20m
Deal found 10/31![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/246:35 pm -
1 stop27h 26m
Mon 1/45:30 am -
1 stop8h 34m
Deal found 11/3![United Airlines logo]()
$423
This Copa Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 1/2112:06 pm -
1 stop14h 01m
Mon 1/252:13 pm -
1 stop18h 48m
Deal found 11/3![Copa Airlines logo]()
$515
This Booking.com deal was found by Cheapflights users on 11/1. 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.
Wed 11/253:40 pm -
1 stop21h 27m
Sun 12/1311:05 am -
1 stop23h 25m
Deal found 11/1![Air Canada logo]()
$564
This Southwest deal was found by Cheapflights users on 11/2. 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 11/192:40 pm -
1 stop8h 40m
Sat 11/288:40 am -
Nonstop4h 35m
Deal found 11/2![Southwest logo]()
$601
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:26 pm -
1 stop27h 07m
Sat 1/212:26 am -
1 stop15h 07m
Deal found 11/1![Frontier logo]()
$603
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/294:15 pm -
1 stop9h 18m
Sun 1/32:47 pm -
1 stop8h 12m
Deal found 11/2![JetBlue logo]()
$614
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:02 pm -
3 stops28h 08m
Thu 12/316:43 am -
2 stops14h 29m
Deal found 11/4![Multiple Airlines logo]()
$761
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:00 am -
2 stops15h 59m
Sun 1/38:00 pm -
1 stop15h 25m
Deal found 11/1![American Airlines logo]()
$818
This Delta deal was found by Cheapflights users on 10/31. 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 1/146:13 pm -
1 stop7h 44m
Sat 1/305:30 am -
1 stop6h 53m
Deal found 10/31![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:35 pm -
1 stop18h 14m
Sat 1/29:17 am -
Nonstop4h 40m
Deal found 10/31![United Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 11/4. 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 1/133:48 pm -
1 stop8h 32m
Mon 2/15:30 am -
1 stop8h 03m
Deal found 11/4![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/247:30 pm -
1 stop16h 29m
Fri 1/19:17 am -
Nonstop4h 40m
Deal found 11/3![United Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 11/1. 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 1/145:10 pm -
1 stop8h 34m
Sat 1/307:38 am -
Nonstop4h 37m
Deal found 11/1![United Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 12/251:59 pm -
1 stop10h 23m
Mon 1/46:00 am -
1 stop6h 23m
Deal found 11/4![Delta logo]()
$439
This Copa Airlines deal was found by Cheapflights users on 10/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/37:02 pm -
1 stop19h 44m
Sun 2/72:13 pm -
1 stop23h 55m
Deal found 10/31![Copa Airlines logo]()
$538
This Copa Airlines deal was found by Cheapflights users on 10/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2012:43 pm -
1 stop13h 28m
Fri 1/12:13 pm -
1 stop19h 29m
Deal found 10/31![Copa Airlines logo]()
$557
This Expedia deal was found by Cheapflights users on 10/31. 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.
Fri 2/512:15 pm -
1 stop9h 37m
Fri 2/128:50 pm -
2 stops48h 30m
Deal found 10/31![Air Canada logo]()
$624
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/223:40 pm -
1 stop8h 42m
Fri 1/86:00 am -
1 stop8h 48m
Deal found 11/4![Delta logo]()
$510
This Copa Airlines deal was found by Cheapflights users on 10/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/52:19 pm -
1 stop11h 52m
Fri 2/122:13 pm -
1 stop18h 49m
Deal found 10/31![Copa Airlines logo]()
$610
This Delta deal was found by Cheapflights users on 10/31. 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 12/243:40 pm -
1 stop8h 42m
Fri 1/16:00 am -
1 stop7h 24m
Deal found 10/31![Delta logo]()
$510
This JetBlue deal was found by Cheapflights users on 11/1. 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.
Mon 1/112:42 pm -
1 stop11h 05m
Mon 2/82:55 pm -
1 stop10h 05m
Deal found 11/1![JetBlue logo]()
$760
This OneTravel deal was found by Cheapflights users on 11/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:26 pm -
2 stops10h 35m
Mon 1/48:35 pm -
2 stops42h 45m
Deal found 11/4![Frontier logo]()
$794
This Booking.com deal was found by Cheapflights users on 11/1. 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.
Wed 11/253:40 pm -
2 stops19h 43m
Sun 12/138:30 am -
3 stops26h 00m
Deal found 11/1![Multiple Airlines logo]()
$806
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 2/32:53 pm -
2 stops22h 22m
Sat 2/67:55 pm -
2 stops17h 11m
Deal found 10/30![United Airlines logo]()
$608
This Copa Airlines deal was found by Cheapflights users on 11/3. 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.
Sat 12/267:03 pm -
1 stop19h 43m
Sat 1/97:35 am -
1 stop16h 29m
Deal found 11/3![Copa Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 11/4. 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 12/243:40 pm -
1 stop8h 42m
Mon 1/46:00 am -
1 stop6h 23m
Deal found 11/4![Delta logo]()
$534
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 2/46:00 am -
1 stop18h 10m
Sat 2/67:05 am -
1 stop14h 41m
Deal found 11/2![United Airlines logo]()
$608
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/113:54 pm -
1 stop10h 13m
Mon 2/85:30 am -
2 stops17h 23m
Deal found 11/3![Multiple Airlines logo]()
$817
Last-minute flights from Dominican Republic to ChicagoDiscover last-minute flight deals from Dominican Republic to Chicago. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Dominican Republic to Chicago. Data last updated November 4, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 10/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:30 pm -
Nonstop5h 10m
Sat 11/2811:10 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$324
This Booking.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/217:00 am -
Nonstop5h 10m
Sat 11/2811:10 am -
Nonstop4h 45m
Deal found 10/30![Arajet logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/131:27 pm -
1 stop8h 57m
Sun 1/1010:31 pm -
1 stop16h 49m
Deal found 11/4![Frontier logo]()
$397
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:25 pm -
1 stop28h 51m
Sun 1/108:30 pm -
1 stop14h 51m
Deal found 11/4![Frontier logo]()
$460
This eDestinos deal was found by Cheapflights users on 10/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:10 pm -
Nonstop5h 10m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$308
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/204:07 pm -
1 stop11h 26m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 10/31![Multiple Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 10/31. 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.
Sun 12/204:49 pm -
1 stop7h 33m
Fri 1/16:00 am -
1 stop8h 49m
Deal found 10/31![Delta logo]()
$416
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
Nonstop5h 10m
Sun 1/34:20 am -
Nonstop4h 45m
Deal found 11/3![Arajet logo]()
$336
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
Nonstop5h 10m
Sat 1/211:10 am -
Nonstop4h 45m
Deal found 11/1![Arajet logo]()
$371
This FlightHub deal was found by Cheapflights users on 11/4. 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 12/247:30 pm -
Nonstop5h 10m
Fri 1/15:45 am -
Nonstop4h 45m
Deal found 11/4![Arajet logo]()
$381
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 12/251:59 pm -
1 stop10h 23m
Mon 1/46:00 am -
1 stop6h 23m
Deal found 11/4![Delta logo]()
$439
This Booking.com deal was found by Cheapflights users on 10/31. 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 12/267:00 am -
Nonstop5h 10m
Sat 1/211:10 am -
Nonstop4h 45m
Deal found 10/31![Arajet logo]()
$387
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 November 4, 2026.
Search for one-way flight options from Dominican Republic to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Booking.com deal was found by Cheapflights users on 10/31. 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.
Thu 1/217:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Arajet logo]()
$202
This Arajet deal was found by Cheapflights users on 11/1. 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 11/201:40 am -
1 stop10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$206
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:10 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Arajet logo]()
$213
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Arajet logo]()
$214
This OneTravel deal was found by Cheapflights users on 11/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:25 pm -
1 stop12h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$215
This Super.com deal was found by Cheapflights users on 11/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/147:10 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Arajet logo]()
$216
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:42 pm -
1 stop8h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/277:00 am -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Arajet logo]()
$220
This OneTravel deal was found by Cheapflights users on 11/4. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:25 pm -
1 stop28h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$223
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:34 pm -
Nonstop5h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$225
This JetBlue deal was found by Cheapflights users on 10/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:50 pm -
1 stop10h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![JetBlue logo]()
$229
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 12/24:55 pm -
1 stop7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$230
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $308 (eDestinos) |
One-way from | $202 (Booking.com) |
Popular in | June |
Cheapest in | October |
Average price | $420 |
Good round-trip deal | $250 or less |
Good one-way deal | $213 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 7,457,451 searches. Data last updated November 4, 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
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 12/25
2:50 pm-11:33 pm
1 stop10h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$229
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Fri 12/25
4:49 pm-10:22 pm
1 stop7h 33m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Wed 12/2
4:55 pm-10:54 pm
1 stop7h 59m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Mon 12/21
1:59 pm-10:22 pm
1 stop10h 23m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Tue 12/22
1:59 pm-9:54 pm
1 stop9h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Fri 12/25
1:59 pm-8:03 pm
1 stop8h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Wed 12/2
2:40 pm-11:56 pm
1 stop11h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Mon 12/21
4:49 pm-12:02 am
1 stop9h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$230
Punta CanaChicago
PUJ Punta Cana - MDW Chicago Midway
PUJMDW
Punta Cana
Thu 12/3
2:40 pm-10:54 pm
1 stop10h 14m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$234
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sat 12/26
6:14 pm-8:55 am
1 stop16h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$234
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Dominican Republic to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Dominican Republic with our price prediction graph.
PUJ-ORD
PUJ-MDW
STI-ORD
SDQ-MDW
SDQ-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
PUJ-ORD
PUJ-MDW
STI-ORD
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 $358). Flying from Dominican Republic to Chicago in March is currently the most expensive (average of $781). 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 November 4, 2026.
It’s optimal to fly from Dominican Republic to Chicago in the evening. By choosing this option you can save up to 58% 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 November 4, 2026.
The most flights from DO0 to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Thursday, 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 November 4, 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.
Boarding
7.4
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.0
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Boarding
7.4
Comfort
7.2
Food
6.4
Entertainment
6.8
Crew
7.9
Overall
7.0
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - 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
Merrillville
Lansing
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
Chicago flight routes
Complete your trip
Flights by cabin class
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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 November 4, 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 November 4, 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$656 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$375 | Average$411 | FlexibilityNo cancel fee | On-time62% |