$182+ Cheap flights from Midway (MDW) 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Jun 11 — Jun 181
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Dominican Republic with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 Midway to Dominican Republic
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Cheapest flights from Midway to Dominican RepublicExplore the most affordable flight options available from Midway to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
Explore the most affordable flight options available from Midway to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
This Priceline deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Wed 8/53:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/9![Frontier logo]()
$377
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sat 8/83:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/11![Frontier logo]()
$392
This Mytrip deal was found by Cheapflights users on 5/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:04 pm
MDW
- PUJ
1 stop25h 42m
Frontier
Sat 7/113:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/6![Frontier logo]()
$393
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Mon 8/103:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/7![Frontier logo]()
$395
This Gotogate deal was found by Cheapflights users on 5/7. 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.
Mon 7/276:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Tue 8/43:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/7![Frontier logo]()
$397
This Priceline deal was found by Cheapflights users on 5/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sat 7/253:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/8![Frontier logo]()
$398
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 22m
Frontier
Deal found 5/6![Frontier logo]()
$406
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Sat 8/153:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/8![Frontier logo]()
$411
This CheapOair deal was found by Cheapflights users on 5/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sat 8/153:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/6![Frontier logo]()
$412
This Gotogate deal was found by Cheapflights users on 5/7. 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.
Sun 7/266:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Tue 8/43:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/7![Frontier logo]()
$417
This Priceline deal was found by Cheapflights users on 5/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Sat 8/83:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/6![Frontier logo]()
$418
This Priceline deal was found by Cheapflights users on 5/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:27 pm
MDW
- PUJ
1 stop24h 58m
Frontier
Mon 8/243:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/8![Frontier logo]()
$419
Best flights from Midway to Dominican RepublicDiscover carefully curated flight deals from Midway to Dominican Republic that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
Discover carefully curated flight deals from Midway to Dominican Republic that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
This Southwest deal was found by Cheapflights users on 5/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:55 pm
MDW
- PUJ
2 stops16h 25m
Southwest
Tue 9/221:45 pm
PUJ
- MDW
2 stops9h 05m
Southwest
Deal found 5/8![Southwest logo]()
$579
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/69:22 am
MDW
- SDQ
2 stops14h 19m
Delta
Sun 6/147:35 pm
SDQ
- MDW
2 stops15h 34m
Delta
Deal found 5/9![Delta logo]()
$597
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/286:00 am
MDW
- SDQ
1 stop6h 16m
Delta
Sat 7/42:41 pm
SDQ
- MDW
1 stop8h 36m
Delta
Deal found 5/11![Delta logo]()
$606
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:10 am
MDW
- PUJ
1 stop7h 40m
Southwest
Thu 10/221:25 pm
PUJ
- MDW
1 stop8h 50m
Southwest
Deal found 5/6![Southwest logo]()
$628
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- PUJ
1 stop6h 20m
Delta
Fri 9/42:52 pm
PUJ
- MDW
1 stop7h 54m
Delta
Deal found 5/11![Delta logo]()
$620
This Delta deal was found by Cheapflights users on 5/7. 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 9/56:00 am
MDW
- PUJ
1 stop7h 51m
Delta
Sat 9/122:45 pm
PUJ
- MDW
1 stop8h 01m
Delta
Deal found 5/7![Delta logo]()
$640
This Southwest deal was found by Cheapflights users on 5/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:35 am
MDW
- PUJ
Nonstop4h 25m
Southwest
Tue 8/42:15 pm
PUJ
- MDW
1 stop7h 30m
Southwest
Deal found 5/8![Southwest logo]()
$741
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/55:08 pm
MDW
- PUJ
1 stop17h 32m
Delta
Tue 6/92:00 pm
PUJ
- MDW
2 stops21h 09m
Delta
Deal found 5/9![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:35 pm
MDW
- PUJ
2 stops18h 00m
Southwest
Sat 8/14:50 pm
PUJ
- MDW
2 stops15h 20m
Southwest
Deal found 5/6![Southwest logo]()
$745
This Delta deal was found by Cheapflights users on 5/7. 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.
Tue 6/96:00 am
MDW
- SDQ
1 stop6h 16m
Delta
Sat 6/137:35 pm
SDQ
- MDW
2 stops15h 34m
Delta
Deal found 5/7![Delta logo]()
$701
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:35 pm
MDW
- PUJ
2 stops16h 50m
Southwest
Sat 7/254:50 pm
PUJ
- MDW
2 stops15h 20m
Southwest
Deal found 5/6![Southwest logo]()
$790
This Delta deal was found by Cheapflights users on 5/8. 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.
Mon 6/19:23 am
MDW
- SDQ
2 stops14h 18m
Delta
Mon 6/87:35 pm
SDQ
- MDW
2 stops15h 34m
Delta
Deal found 5/8![Delta logo]()
$701
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:05 am
MDW
- PUJ
1 stop7h 40m
Southwest
Mon 10/121:25 pm
PUJ
- MDW
1 stop12h 15m
Southwest
Deal found 5/6![Southwest logo]()
$808
This Delta deal was found by Cheapflights users on 5/8. 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 6/126:00 am
MDW
- SDQ
2 stops11h 04m
Delta
Mon 6/157:35 pm
SDQ
- MDW
2 stops15h 34m
Delta
Deal found 5/8![Delta logo]()
$737
This Delta deal was found by Cheapflights users on 5/6. 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.
Mon 10/56:00 am
MDW
- PUJ
1 stop7h 32m
Delta
Tue 10/132:49 pm
PUJ
- MDW
1 stop7h 56m
Delta
Deal found 5/6![Delta logo]()
$740
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/286:23 am
MDW
- PUJ
1 stop7h 12m
Delta
Thu 6/41:05 pm
PUJ
- MDW
1 stop9h 04m
Delta
Deal found 5/10![Delta logo]()
$796
This Delta deal was found by Cheapflights users on 5/8. 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.
Mon 7/276:00 am
MDW
- SDQ
2 stops11h 06m
Delta
Mon 8/32:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 5/8![Delta logo]()
$802
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/199:22 am
MDW
- SDQ
2 stops14h 16m
Delta
Wed 5/272:48 pm
SDQ
- MDW
1 stop7h 21m
Delta
Deal found 5/10![Delta logo]()
$891
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/156:00 am
MDW
- SDQ
1 stop6h 16m
Delta
Sat 6/202:41 pm
SDQ
- MDW
1 stop8h 36m
Delta
Deal found 5/9![Delta logo]()
$902
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/319:22 am
MDW
- STI
2 stops14h 37m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops14h 10m
Delta
Deal found 5/10![Delta logo]()
$1,188
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/204:25 pm
MDW
- STI
2 stops19h 00m
Delta
Sat 7/46:00 am
STI
- MDW
2 stops12h 07m
Delta
Deal found 5/10![Delta logo]()
$2,506
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 6/106:00 am
MDW
- STI
2 stops12h 33m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops14h 10m
Delta
Deal found 5/7![Delta logo]()
$2,771
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/79:17 am
MDW
- STI
2 stops15h 42m
Delta
Fri 6/128:59 pm
STI
- MDW
2 stops17h 10m
Delta
Deal found 5/11![Delta logo]()
$2,932
This Delta deal was found by Cheapflights users on 5/8. 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 6/1212:50 pm
MDW
- STI
2 stops12h 09m
Delta
Mon 6/228:59 pm
STI
- MDW
2 stops14h 10m
Delta
Deal found 5/8![Delta logo]()
$2,932
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/296:23 am
MDW
- STI
2 stops12h 05m
Delta
Sun 6/78:59 pm
STI
- MDW
2 stops16h 06m
Delta
Deal found 5/11![Delta logo]()
$3,369
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/2212:53 pm
MDW
- STI
2 stops11h 06m
Delta
Mon 6/16:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 5/10![Delta logo]()
$4,527
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated May 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/8. 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 5/269:23 am
MDW
- SDQ
2 stops14h 18m
Delta
Tue 6/166:06 am
SDQ
- MDW
2 stops13h 25m
Delta
Deal found 5/8![Delta logo]()
$552
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Tue 6/23:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Deal found 5/8![Frontier logo]()
$432
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Tue 6/23:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Deal found 5/7![Frontier logo]()
$434
This Gotogate deal was found by Cheapflights users on 5/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MDW
- PUJ
2 stops27h 35m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/8![Frontier logo]()
$422
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MDW
- PUJ
2 stops27h 35m
Frontier
Sat 6/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/11![Frontier logo]()
$437
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/11![Frontier logo]()
$429
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Sat 6/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/11![Frontier logo]()
$443
This Priceline deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- PUJ
2 stops28h 55m
Frontier
Sat 6/133:40 pm
PUJ
- MDW
1 stop20h 32m
Frontier
Deal found 5/10![Frontier logo]()
$417
This Frontier deal was found by Cheapflights users on 5/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Wed 6/1011:42 am
PUJ
- MDW
2 stops11h 29m
Frontier
Deal found 5/7![Frontier logo]()
$426
This Delta deal was found by Cheapflights users on 5/7. 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.
Tue 6/96:00 am
MDW
- SDQ
2 stops11h 04m
Delta
Sat 6/137:35 pm
SDQ
- MDW
2 stops15h 34m
Delta
Deal found 5/7![Delta logo]()
$507
This Mytrip deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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.
Tue 6/166:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Tue 7/143:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/9![Frontier logo]()
$428
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Wed 7/811:46 am
PUJ
- MDW
2 stops11h 22m
Frontier
Deal found 5/10![Frontier logo]()
$441
One-way flights from Midway to Dominican RepublicSearch for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Deal found 5/10![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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.
Sat 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Deal found 5/9![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/10![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 5/10![Frontier logo]()
$198
This Trip.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Deal found 5/10![Frontier logo]()
$204
This Priceline deal was found by Cheapflights users on 5/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:11 pm
MDW
- PUJ
1 stop25h 38m
Frontier
Deal found 5/7![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/11![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:11 pm
MDW
- PUJ
2 stops21h 25m
Frontier
Deal found 5/8![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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.
Sun 7/266:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/9![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:11 pm
MDW
- PUJ
2 stops30h 43m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$214
This CheapOair deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Tue 5/266:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 5/11![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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.
Tue 6/212:27 pm
MDW
- SDQ
2 stops27h 02m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$238
Find flight deals from Midway to Dominican Republic
Keep the following information in mind while searching for Midway to Dominican Republic flight deals. Data was last updated May 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (Priceline) |
One-way from | $182 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $506 |
Good round-trip deal | $605 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 May 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 9/14
7:55 pm-1:20 pm
2 stops16h 25m
Punta Cana
Tue 9/22
1:45 pm-9:50 pm
2 stops9h 05m
$579
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 6/6
9:22 am-12:41 am
2 stops14h 19m
Santo Domingo Las Americas
Sun 6/14
7:35 pm-10:09 am
2 stops15h 34m
$597
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sun 6/28
6:00 am-1:16 pm
1 stop6h 16m
Santo Domingo Las Americas
Sat 7/4
2:41 pm-10:17 pm
1 stop8h 36m
$606
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 8/27
6:05 am-1:25 pm
1 stop6h 20m
Punta Cana
Fri 9/4
2:52 pm-9:46 pm
1 stop7h 54m
$620
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 10/18
5:10 am-1:50 pm
1 stop7h 40m
Punta Cana
Thu 10/22
1:25 pm-9:15 pm
1 stop8h 50m
$628
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 9/5
6:00 am-2:51 pm
1 stop7h 51m
Punta Cana
Sat 9/12
2:45 pm-9:46 pm
1 stop8h 01m
$640
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 6/5
5:08 pm-11:40 am
1 stop17h 32m
Punta Cana
Tue 6/9
2:00 pm-10:09 am
2 stops21h 09m
$675
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Tue 6/9
6:00 am-1:16 pm
1 stop6h 16m
Santo Domingo Las Americas
Sat 6/13
7:35 pm-10:09 am
2 stops15h 34m
$701
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Mon 6/1
9:23 am-12:41 am
2 stops14h 18m
Santo Domingo Las Americas
Mon 6/8
7:35 pm-10:09 am
2 stops15h 34m
$701
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Fri 6/12
6:00 am-6:04 pm
2 stops11h 04m
Santo Domingo Las Americas
Mon 6/15
7:35 pm-10:09 am
2 stops15h 34m
$737
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Midway to Dominican Republic
Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Midway with our price prediction graph.
MDW-PUJ
MDW-SDQ
MDW-STI
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 Midway Airport to the Dominican Republic
MDW-DO0
MDW-PUJ
MDW-SDQ
MDW-STI
What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $190). Flying from Chicago Midway Airport to Dominican Republic in December is currently the most expensive (average of $860). 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 MDW to DO?
Find hourly flight availability from Midway 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 May 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Dominican Republic as you normally would.
How often are flights from Chicago to the Dominican Republic delayed?
About 25% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 96 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 morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday 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, Southwest have had the lowest number of delays on this route, with just 25% of flights being delayed.
Reviews of airlines servicing Dominican Republic
Get insights into the airlines that provide service to Dominican Republic. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Dominican Republic. Reviews last updated May 12, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to the Dominican Republic, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway 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 Midway 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 Midway to Dominican Republic by cabin class
Find flights from Midway to Dominican Republic, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Dominican Republic flights
Browse other Midway and Dominican Republic flight options. Last updated on May 12, 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 3 airlines flying from Midway to Dominican Republic
Discover the top 3 airlines that operate flights from Midway 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 May 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$416 | Average$666 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$539 | Average$779 | FlexibilityNo cancel fee | On-timeN/A |