$131+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Mar 5 — Mar 121
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
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 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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- PUJ
1 stop10h 23m
Multiple Airlines
Fri 3/64:32 pm
PUJ
- MDW
1 stop7h 47m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Mon 3/96:00 am
MDW
- SDQ
1 stop9h 29m
Multiple Airlines
Mon 3/302:52 am
SDQ
- MDW
2 stops13h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- PUJ
1 stop10h 23m
Multiple Airlines
Sat 3/72:16 pm
PUJ
- MDW
1 stop9h 29m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- SDQ
1 stop9h 29m
Multiple Airlines
Tue 3/175:30 am
SDQ
- MDW
1 stop8h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$336
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- PUJ
1 stop6h 46m
Frontier
Sat 5/92:56 pm
PUJ
- MDW
1 stop8h 23m
Frontier
Deal found 2/1![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sat 2/218:00 am
MDW
- SDQ
1 stop23h 39m
Multiple Airlines
Wed 2/253:32 pm
SDQ
- MDW
2 stops26h 44m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
- SDQ
1 stop13h 30m
Multiple Airlines
Mon 3/97:10 pm
SDQ
- MDW
1 stop18h 52m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:00 am
MDW
- PUJ
1 stop8h 31m
Multiple Airlines
Tue 3/103:32 pm
PUJ
- MDW
2 stops19h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/116:05 am
MDW
- PUJ
2 stops12h 49m
Multiple Airlines
Sat 3/141:21 pm
PUJ
- MDW
1 stop9h 24m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 5/17:30 am
MDW
- SDQ
1 stop20h 59m
Multiple Airlines
Mon 5/46:10 am
SDQ
- MDW
1 stop7h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/162:19 pm
MDW
- SDQ
2 stops19h 37m
Frontier
Thu 2/1912:31 pm
SDQ
- MDW
1 stop27h 55m
Frontier
Deal found 2/2![Frontier logo]()
$350
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SDQ
1 stop12h 34m
Frontier
Mon 3/910:46 am
SDQ
- MDW
1 stop11h 07m
Frontier
Deal found 2/2![Frontier logo]()
$353
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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sat 2/218:00 am
MDW
- SDQ
1 stop23h 39m
Multiple Airlines
Wed 2/253:32 pm
SDQ
- MDW
2 stops26h 44m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$341
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:00 am
MDW
- SDQ
1 stop23h 39m
Frontier
Sat 3/711:56 am
SDQ
- MDW
1 stop11h 49m
Frontier
Deal found 1/31![Frontier logo]()
$394
This Delta deal was found by Cheapflights users on 2/1. 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.
Sun 4/266:00 am
MDW
- PUJ
1 stop7h 32m
Delta
Wed 4/292:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 2/1![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:00 am
MDW
- PUJ
1 stop7h 30m
Southwest
Tue 3/101:25 pm
PUJ
- MDW
1 stop10h 15m
Southwest
Deal found 2/3![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 4/77:20 pm
MDW
- PUJ
1 stop16h 45m
Delta
Wed 4/152:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 2/1![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:15 am
MDW
- PUJ
Nonstop4h 15m
Southwest
Sun 3/153:25 pm
PUJ
- MDW
Nonstop5h 10m
Southwest
Deal found 2/3![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
MDW
- PUJ
1 stop8h 40m
Delta
Wed 3/184:42 pm
PUJ
- MDW
2 stops20h 47m
Delta
Deal found 2/2![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/1. 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 4/66:07 pm
MDW
- PUJ
2 stops17h 01m
Delta
Wed 4/152:20 pm
PUJ
- MDW
2 stops19h 27m
Delta
Deal found 2/1![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/1. 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 3/237:20 pm
MDW
- PUJ
1 stop16h 45m
Delta
Tue 3/313:50 pm
PUJ
- MDW
2 stops21h 39m
Delta
Deal found 2/1![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 4/77:20 pm
MDW
- PUJ
1 stop16h 45m
Delta
Thu 4/162:46 pm
PUJ
- MDW
2 stops19h 01m
Delta
Deal found 2/1![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:34 pm
MDW
- PUJ
2 stops17h 06m
Delta
Wed 3/184:42 pm
PUJ
- MDW
2 stops20h 47m
Delta
Deal found 2/2![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
MDW
- PUJ
1 stop8h 40m
Delta
Wed 4/13:18 pm
PUJ
- MDW
2 stops18h 35m
Delta
Deal found 2/2![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 2/1. 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 3/116:00 am
MDW
- SDQ
1 stop6h 10m
Delta
Tue 3/172:35 pm
SDQ
- MDW
1 stop8h 56m
Delta
Deal found 2/1![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 1/31. 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.
Sat 2/216:00 am
MDW
- SDQ
1 stop7h 30m
Delta
Wed 2/253:42 pm
SDQ
- MDW
1 stop8h 49m
Delta
Deal found 1/31![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 2/1. 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.
Fri 4/176:00 am
MDW
- SDQ
1 stop6h 12m
Delta
Sat 4/252:37 pm
SDQ
- MDW
1 stop8h 51m
Delta
Deal found 2/1![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 2/1. 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.
Thu 3/59:34 am
MDW
- SDQ
2 stops12h 58m
Delta
Tue 3/106:57 am
SDQ
- MDW
2 stops11h 57m
Delta
Deal found 2/1![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 2/1. 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.
Fri 4/107:20 pm
MDW
- PUJ
1 stop18h 30m
Delta
Wed 4/151:00 pm
PUJ
- MDW
1 stop10h 28m
Delta
Deal found 2/1![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 2/1. 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.
Fri 4/107:20 pm
MDW
- PUJ
1 stop16h 45m
Delta
Tue 4/142:20 pm
PUJ
- MDW
2 stops19h 27m
Delta
Deal found 2/1![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:26 pm
MDW
- STI
2 stops9h 24m
Delta
Mon 2/96:39 am
STI
- MDW
2 stops13h 57m
Delta
Deal found 2/2![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/89:33 am
MDW
- STI
2 stops13h 17m
Delta
Sun 2/159:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$980
This Delta deal was found by Cheapflights users on 2/1. 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 2/161:26 pm
MDW
- STI
2 stops10h 08m
Delta
Mon 3/29:59 pm
STI
- MDW
2 stops16h 00m
Delta
Deal found 2/1![Delta logo]()
$1,119
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2710:45 am
MDW
- STI
2 stops12h 09m
Delta
Sun 3/298:40 pm
STI
- MDW
2 stops16h 49m
Delta
Deal found 2/2![Delta logo]()
$6,014
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated February 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/162:19 pm
MDW
- SDQ
2 stops19h 37m
Frontier
Thu 2/1912:31 pm
SDQ
- MDW
1 stop27h 55m
Frontier
Deal found 2/2![Frontier logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Sat 2/218:00 am
MDW
- SDQ
1 stop23h 39m
Multiple Airlines
Wed 2/253:32 pm
SDQ
- MDW
2 stops26h 44m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
MDW
- SDQ
2 stops29h 20m
Multiple Airlines
Wed 3/2510:19 am
SDQ
- MDW
1 stop8h 29m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- PUJ
1 stop10h 23m
Multiple Airlines
Fri 3/64:32 pm
PUJ
- MDW
1 stop7h 47m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
- PUJ
1 stop10h 23m
Multiple Airlines
Sat 3/72:16 pm
PUJ
- MDW
1 stop9h 29m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$333
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
- SDQ
1 stop12h 34m
Frontier
Mon 3/910:46 am
SDQ
- MDW
1 stop11h 07m
Frontier
Deal found 2/2![Frontier logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
- SDQ
1 stop13h 30m
Multiple Airlines
Mon 3/97:10 pm
SDQ
- MDW
1 stop18h 52m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
- PUJ
1 stop8h 16m
Multiple Airlines
Sat 3/72:16 pm
PUJ
- MDW
1 stop9h 29m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:00 am
MDW
- PUJ
1 stop8h 31m
Multiple Airlines
Tue 3/103:32 pm
PUJ
- MDW
2 stops19h 53m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Mon 3/96:00 am
MDW
- SDQ
1 stop9h 29m
Multiple Airlines
Mon 3/302:52 am
SDQ
- MDW
2 stops13h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- SDQ
1 stop9h 29m
Multiple Airlines
Tue 3/175:30 am
SDQ
- MDW
1 stop8h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/116:05 am
MDW
- PUJ
2 stops12h 49m
Multiple Airlines
Sat 3/141:21 pm
PUJ
- MDW
1 stop9h 24m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$346
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 February 3, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:48 pm
MDW
- PUJ
1 stop17h 17m
Frontier
Deal found 2/3![Frontier logo]()
$131
This Trip.com deal was found by Cheapflights users on 2/3. 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 3/56:15 am
MDW
- PUJ
1 stop8h 16m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- PUJ
1 stop14h 29m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$139
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Sat 3/76:00 am
MDW
- PUJ
1 stop8h 31m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$140
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Sun 3/86:00 am
MDW
- PUJ
1 stop11h 38m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$146
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Sun 3/16:15 am
MDW
- PUJ
1 stop10h 23m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
MDW
- PUJ
1 stop31h 17m
Frontier
Deal found 2/3![Frontier logo]()
$148
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:00 am
MDW
- PUJ
1 stop14h 29m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 2/176:00 am
MDW
- PUJ
2 stops32h 36m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$150
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:05 am
MDW
- PUJ
1 stop7h 12m
Frontier
Deal found 2/1![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
MDW
- PUJ
1 stop31h 17m
Frontier
Deal found 2/3![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- PUJ
1 stop13h 59m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$155
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $328 (Kiwi.com) |
One-way from | $131 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $469 |
Good round-trip deal | $637 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 February 3, 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
Midway
Fly to
Dominican Republic
Route
Depart
Return
Price
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 2/21
8:00 am-9:39 am
1 stop23h 39m
Santo Domingo Las Americas
Wed 2/25
3:32 pm-4:16 pm
2 stops26h 44m
$341
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 2/28
8:00 am-9:39 am
1 stop23h 39m
Santo Domingo Las Americas
Sat 3/7
11:56 am-9:45 pm
1 stop11h 49m
$394
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/26
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
Wed 4/29
2:46 pm-10:28 pm
1 stop8h 42m
$397
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 3/3
5:00 am-2:30 pm
1 stop7h 30m
Punta Cana
Tue 3/10
1:25 pm-10:40 pm
1 stop10h 15m
$397
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 4/7
7:20 pm-1:05 pm
1 stop16h 45m
Punta Cana
Wed 4/15
2:46 pm-10:28 pm
1 stop8h 42m
$397
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 3/17
6:00 am-3:40 pm
1 stop8h 40m
Punta Cana
Wed 3/18
4:42 pm-12:29 pm
2 stops20h 47m
$401
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 4/6
6:07 pm-12:08 pm
2 stops17h 01m
Punta Cana
Wed 4/15
2:20 pm-8:47 am
2 stops19h 27m
$401
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 3/23
7:20 pm-1:05 pm
1 stop16h 45m
Punta Cana
Tue 3/31
3:50 pm-12:29 pm
2 stops21h 39m
$401
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 4/7
7:20 pm-1:05 pm
1 stop16h 45m
Punta Cana
Thu 4/16
2:46 pm-8:47 am
2 stops19h 01m
$401
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 3/16
6:34 pm-12:40 pm
2 stops17h 06m
Punta Cana
Wed 3/18
4:42 pm-12:29 pm
2 stops20h 47m
$401
Showing 1-10 of 41 results
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-SDQ
MDW-PUJ
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-SDQ
MDW-PUJ
MDW-STI
What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $252). Flying from Chicago Midway Airport to Dominican Republic in December is currently the most expensive (average of $863). 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 February 3, 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 22% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 112 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 Sunday 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 22% 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 February 3, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to the Dominican Republic, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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
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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 February 3, 2026.
Popular flight searches
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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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$406 | Average$622 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$419 | Average$660 | FlexibilityNo cancel fee | On-time63% |