$178+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Dominican Republic with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from 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 August 6, 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 August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop10h 00m
Deal found 8/4![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am -
1 stop6h 20m
Fri 9/44:04 pm -
2 stops18h 13m
Deal found 8/4![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:20 am -
1 stop7h 20m
Sat 11/214:10 pm -
Nonstop5h 05m
Deal found 8/4![Southwest logo]()
$450
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:04 am -
2 stops10h 29m
Tue 11/109:00 pm -
2 stops17h 05m
Deal found 8/2![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:00 am -
1 stop7h 55m
Wed 9/22:15 pm -
1 stop7h 30m
Deal found 8/3![Southwest logo]()
$460
This Frontier deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am -
1 stop7h 22m
Sat 9/53:37 pm -
1 stop8h 10m
Deal found 8/6![Frontier logo]()
$483
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Sat 9/51:25 pm -
1 stop8h 10m
Deal found 8/3![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:20 am -
1 stop7h 20m
Sat 11/214:10 pm -
Nonstop5h 05m
Deal found 8/2![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:45 am -
1 stop7h 00m
Sun 11/14:50 pm -
2 stops17h 50m
Deal found 8/5![Southwest logo]()
$505
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am -
1 stop6h 23m
Sat 9/52:53 pm -
1 stop8h 43m
Deal found 8/4![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:42 pm -
2 stops17h 46m
Wed 8/262:53 pm -
1 stop8h 43m
Deal found 8/1![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am -
1 stop6h 22m
Tue 9/292:53 pm -
1 stop8h 51m
Deal found 8/3![Delta logo]()
$540
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 August 6, 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 August 6, 2026.
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:04 am -
2 stops10h 29m
Tue 11/109:00 pm -
2 stops17h 05m
Deal found 8/2![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:15 am -
1 stop6h 05m
Wed 9/232:15 pm -
1 stop7h 35m
Deal found 8/2![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am -
1 stop6h 23m
Sat 9/52:53 pm -
1 stop8h 43m
Deal found 8/6![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:05 am -
1 stop6h 22m
Sat 9/192:53 pm -
1 stop8h 51m
Deal found 8/4![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop6h 40m
Sat 12/123:55 pm -
1 stop9h 01m
Deal found 8/5![Delta logo]()
$520
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:55 pm -
2 stops16h 25m
Wed 9/301:45 pm -
2 stops9h 40m
Deal found 8/1![Southwest logo]()
$646
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:55 pm -
2 stops16h 25m
Thu 9/172:35 pm -
1 stop7h 25m
Deal found 8/2![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am -
1 stop6h 22m
Thu 9/242:53 pm -
1 stop8h 51m
Deal found 8/3![Delta logo]()
$605
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:00 am -
1 stop7h 55m
Fri 9/251:45 pm -
2 stops18h 50m
Deal found 8/4![Southwest logo]()
$701
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop6h 40m
Tue 11/173:55 pm -
1 stop9h 01m
Deal found 8/3![Delta logo]()
$605
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:45 am -
1 stop7h 00m
Wed 10/142:45 pm -
2 stops19h 00m
Deal found 8/4![Southwest logo]()
$717
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:31 pm -
2 stops18h 09m
Wed 10/144:05 pm -
2 stops21h 42m
Deal found 8/6![Delta logo]()
$610
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:30 pm -
2 stops16h 55m
Tue 10/62:45 pm -
2 stops18h 40m
Deal found 8/5![Southwest logo]()
$717
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
2 stops11h 35m
Thu 12/106:40 am -
2 stops13h 24m
Deal found 8/6![Delta logo]()
$610
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:10 am -
1 stop8h 40m
Mon 11/94:50 pm -
2 stops18h 10m
Deal found 8/3![Southwest logo]()
$721
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am -
1 stop6h 22m
Sat 9/262:53 pm -
1 stop8h 51m
Deal found 8/5![Delta logo]()
$641
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:55 am -
1 stop6h 10m
Fri 9/111:45 pm -
1 stop10h 00m
Deal found 8/5![Southwest logo]()
$753
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/161:00 pm -
2 stops9h 30m
Tue 1/193:40 pm -
1 stop8h 30m
Deal found 8/4![Delta logo]()
$727
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am -
1 stop6h 05m
Mon 10/52:45 pm -
1 stop8h 15m
Deal found 8/1![Southwest logo]()
$833
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am -
2 stops11h 01m
Tue 9/152:53 pm -
1 stop8h 51m
Deal found 8/6![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/161:00 pm -
2 stops9h 30m
Sat 1/233:40 pm -
1 stop8h 30m
Deal found 8/1![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:05 am -
1 stop7h 34m
Thu 8/274:04 pm -
1 stop7h 32m
Deal found 8/4![Delta logo]()
$736
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:30 am -
2 stops13h 25m
Tue 12/156:40 am -
2 stops13h 24m
Deal found 8/6![Delta logo]()
$1,772
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
2 stops18h 50m
Wed 9/97:30 pm -
2 stops23h 49m
Deal found 8/3![Delta logo]()
$2,723
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:25 pm -
2 stops11h 30m
Wed 9/97:30 pm -
2 stops16h 06m
Deal found 8/3![Delta logo]()
$3,673
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated August 6, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am -
1 stop7h 16m
Sat 8/223:37 pm -
1 stop8h 10m
Deal found 8/1![Frontier logo]()
$518
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am -
1 stop6h 23m
Sat 9/52:53 pm -
1 stop8h 43m
Deal found 8/4![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:42 pm -
2 stops17h 46m
Wed 8/262:53 pm -
1 stop8h 43m
Deal found 8/1![Delta logo]()
$525
This Orbitz deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:05 am -
1 stop7h 22m
Sat 8/293:37 pm -
1 stop8h 10m
Deal found 8/2![Frontier logo]()
$516
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am -
1 stop6h 20m
Wed 9/22:50 pm -
1 stop8h 46m
Deal found 8/4![Delta logo]()
$535
This Frontier deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am -
1 stop7h 22m
Sat 9/53:37 pm -
1 stop8h 10m
Deal found 8/6![Frontier logo]()
$483
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:00 am -
1 stop7h 55m
Wed 9/22:15 pm -
1 stop7h 30m
Deal found 8/3![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Thu 9/31:45 pm -
1 stop10h 00m
Deal found 8/4![Southwest logo]()
$390
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:05 am -
1 stop6h 20m
Fri 9/44:04 pm -
2 stops18h 13m
Deal found 8/4![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:00 am -
1 stop7h 40m
Sat 9/51:25 pm -
1 stop8h 10m
Deal found 8/3![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:05 am -
1 stop6h 20m
Sat 9/194:00 pm -
1 stop7h 44m
Deal found 8/5![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am -
1 stop6h 22m
Tue 9/292:53 pm -
1 stop8h 51m
Deal found 8/3![Delta logo]()
$540
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 August 6, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/15:25 pm -
2 stops20h 55m
Deal found 8/4![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:45 pm -
2 stops19h 54m
Deal found 8/4![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:15 pm -
2 stops18h 18m
Deal found 8/4![Delta logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:25 am -
3 stops34h 06m
Deal found 8/4![Multiple Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:25 pm -
2 stops21h 18m
Deal found 8/1![Delta logo]()
$218
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 am -
1 stop7h 22m
Deal found 8/5![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:03 pm -
2 stops26h 28m
Deal found 8/1![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/312:03 pm -
2 stops29h 51m
Deal found 8/1![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
2 stops15h 47m
Deal found 8/6![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:03 pm -
2 stops27h 26m
Deal found 8/2![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:03 pm -
2 stops31h 13m
Deal found 8/4![Multiple Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:06 pm -
3 stops26h 55m
Deal found 8/5![Multiple Airlines logo]()
$240
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $390 (Southwest) |
One-way from | $178 (Delta) |
Popular in | June |
Cheapest in | September |
Average price | $538 |
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 August 6, 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
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Wed 10/28
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Tue 11/10
9:00 pm-12:05 pm
2 stops17h 05m
$455
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Mon 8/17
6:05 am-1:28 pm
1 stop6h 23m
Santo Domingo Las Americas
Sat 9/5
2:53 pm-10:36 pm
1 stop8h 43m
$520
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 9/12
6:05 am-1:27 pm
1 stop6h 22m
Santo Domingo Las Americas
Sat 9/19
2:53 pm-10:44 pm
1 stop8h 51m
$520
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 12/5
6:00 am-2:40 pm
1 stop6h 40m
Santo Domingo Las Americas
Sat 12/12
3:55 pm-10:56 pm
1 stop9h 01m
$520
Quickest round-trip
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Wed 9/16
6:15 am-1:20 pm
1 stop6h 05m
Punta Cana
Wed 9/23
2:15 pm-8:50 pm
1 stop7h 35m
$590
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 9/19
6:05 am-1:27 pm
1 stop6h 22m
Santo Domingo Las Americas
Thu 9/24
2:53 pm-10:44 pm
1 stop8h 51m
$605
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Tue 11/10
6:00 am-2:40 pm
1 stop6h 40m
Santo Domingo Las Americas
Tue 11/17
3:55 pm-10:56 pm
1 stop9h 01m
$605
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 10/10
5:31 pm-12:40 pm
2 stops18h 09m
Punta Cana
Wed 10/14
4:05 pm-12:47 pm
2 stops21h 42m
$610
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Thu 11/26
6:00 am-7:35 pm
2 stops11h 35m
Santiago de los Caballeros
Thu 12/10
6:40 am-6:04 pm
2 stops13h 24m
$610
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 9/19
6:05 am-1:27 pm
1 stop6h 22m
Santo Domingo Las Americas
Sat 9/26
2:53 pm-10:44 pm
1 stop8h 51m
$641
Showing 1-10 of 46 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-STI
MDW-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to the Dominican Republic
MDW-DO0
MDW-PUJ
MDW-STI
MDW-SDQ
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 $515). Flying from Chicago Midway Airport to Dominican Republic in June is currently the most expensive (average of $1,285). 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 August 6, 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 35% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 88 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?
Friday tends to have the lowest number of delays on this route, whereas Wednesday 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 35% 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 August 6, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to the Dominican Republic, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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.
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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 August 6, 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 2 airlines flying from Midway to Dominican Republic
Discover the top 2 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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$478 | Average$960 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$503 | Average$980 | FlexibilityNo cancel fee | On-time63% |