$185+ Cheap flights from Midway (MDW) to the Dominican Republic
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Oct 22 — Oct 291
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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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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/286:20 pm -
1 stop18h 15m
Thu 1/144:20 pm -
1 stop18h 29m
Deal found 9/17![Delta logo]()
$430
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/289:30 am -
2 stops24h 58m
Fri 12/44:55 pm -
2 stops22h 06m
Deal found 9/20![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/107:00 am -
2 stops11h 18m
Deal found 9/20![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/18:40 pm -
2 stops16h 30m
Thu 11/54:05 pm -
1 stop9h 10m
Deal found 9/21![Southwest logo]()
$440
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 9/20![Southwest logo]()
$460
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/288:40 am -
Nonstop4h 35m
Sat 12/53:35 pm -
1 stop8h 05m
Deal found 9/21![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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
Tue 11/32:40 pm -
2 stops10h 00m
Deal found 9/22![Southwest logo]()
$462
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/288:40 am -
Nonstop4h 35m
Thu 12/32:40 pm -
1 stop8h 40m
Deal found 9/17![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 26m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 9/20![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/265:00 am -
1 stop6h 25m
Mon 11/24:50 pm -
2 stops18h 10m
Deal found 9/17![Southwest logo]()
$475
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/279:53 am -
3 stops30h 12m
Tue 11/38:14 am -
2 stops17h 33m
Deal found 9/17![Multiple Airlines logo]()
$480
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:20 am -
1 stop6h 25m
Thu 12/32:40 pm -
1 stop8h 40m
Deal found 9/21![Southwest logo]()
$485
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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/107:00 am -
2 stops11h 18m
Deal found 9/20![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/15:05 am -
1 stop8h 05m
Wed 11/42:40 pm -
1 stop8h 40m
Deal found 9/18![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 26m
Tue 11/35:05 pm -
1 stop7h 28m
Deal found 9/21![Delta logo]()
$510
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/265:00 am -
1 stop6h 25m
Sun 11/14:05 pm -
1 stop9h 00m
Deal found 9/21![Southwest logo]()
$525
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/46:04 am -
1 stop6h 28m
Wed 11/187:02 am -
2 stops13h 02m
Deal found 9/21![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2010:35 am -
2 stops11h 55m
Wed 1/273:40 pm -
1 stop8h 30m
Deal found 9/20![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/1811:27 am -
2 stops12h 47m
Thu 11/263:57 pm -
1 stop8h 57m
Deal found 9/19![Delta logo]()
$525
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/245:00 am -
1 stop7h 00m
Tue 10/272:45 pm -
2 stops18h 40m
Deal found 9/21![Southwest logo]()
$667
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 1/191:00 pm -
2 stops9h 30m
Tue 1/263:40 pm -
1 stop8h 30m
Deal found 9/21![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
1 stop6h 28m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 9/19![Delta logo]()
$530
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:25 pm -
2 stops17h 25m
Tue 11/173:35 pm -
1 stop7h 55m
Deal found 9/20![Southwest logo]()
$725
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/245:25 am -
1 stop8h 25m
Fri 12/42:40 pm -
1 stop8h 35m
Deal found 9/17![Southwest logo]()
$728
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:28 am -
2 stops12h 57m
Sun 12/63:57 pm -
1 stop8h 57m
Deal found 9/21![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 1/186:00 am -
1 stop7h 30m
Mon 1/254:55 pm -
1 stop7h 15m
Deal found 9/21![Delta logo]()
$608
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/226:00 am -
1 stop8h 42m
Thu 1/284:55 pm -
1 stop7h 15m
Deal found 9/19![Delta logo]()
$610
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 3/106:00 am -
1 stop6h 10m
Wed 3/176:35 am -
2 stops16h 35m
Deal found 9/18![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:00 am -
1 stop7h 29m
Wed 12/164:55 pm -
1 stop7h 59m
Deal found 9/19![Delta logo]()
$660
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop6h 28m
Wed 12/94:55 pm -
1 stop7h 59m
Deal found 9/19![Delta logo]()
$660
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:00 pm -
2 stops9h 30m
Wed 1/207:30 am -
2 stops13h 07m
Deal found 9/22![Delta logo]()
$727
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/66:04 am -
1 stop6h 28m
Tue 11/103:57 pm -
1 stop8h 57m
Deal found 9/18![Delta logo]()
$747
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 1/259:30 am -
2 stops13h 00m
Mon 2/17:30 am -
2 stops13h 07m
Deal found 9/21![Delta logo]()
$752
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/119:29 am -
2 stops31h 04m
Fri 10/237:05 pm -
2 stops28h 28m
Deal found 9/20![Delta logo]()
$778
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 stop7h 29m
Sat 12/124:55 pm -
1 stop7h 59m
Deal found 9/21![Delta logo]()
$786
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop6h 28m
Fri 12/112:40 pm -
1 stop10h 15m
Deal found 9/18![Delta logo]()
$838
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
2 stops10h 29m
Mon 11/28:10 pm -
2 stops21h 07m
Deal found 9/20![Delta logo]()
$923
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 2/96:00 am -
2 stops10h 40m
Tue 2/166:35 am -
2 stops14h 02m
Deal found 9/21![Delta logo]()
$1,509
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/119:29 am -
2 stops31h 04m
Fri 10/167:05 pm -
2 stops15h 27m
Deal found 9/20![Delta logo]()
$2,020
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/316:04 am -
2 stops10h 29m
Mon 11/309:25 pm -
2 stops16h 40m
Deal found 9/18![Delta logo]()
$2,189
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/16:04 am -
2 stops10h 29m
Sun 11/88:10 pm -
2 stops22h 08m
Deal found 9/17![Delta logo]()
$2,605
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/66:04 am -
2 stops10h 29m
Mon 11/99:25 pm -
2 stops14h 59m
Deal found 9/20![Delta logo]()
$4,822
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 9/296:05 am -
1 stop6h 22m
Tue 10/62:57 pm -
1 stop8h 36m
Deal found 9/17![Delta logo]()
$522
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/216:04 am -
1 stop6h 28m
Wed 10/282:57 pm -
1 stop8h 36m
Deal found 9/21![Delta logo]()
$520
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/238:40 pm -
2 stops15h 45m
Fri 10/302:45 pm -
1 stop8h 15m
Deal found 9/17![Southwest logo]()
$505
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/265:00 am -
1 stop6h 25m
Mon 11/24:50 pm -
1 stop8h 05m
Deal found 9/18![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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
Tue 11/32:40 pm -
2 stops10h 00m
Deal found 9/22![Southwest logo]()
$462
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/279:53 am -
3 stops30h 12m
Tue 11/38:14 am -
2 stops17h 33m
Deal found 9/17![Multiple Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/276:04 am -
2 stops11h 02m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 9/21![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/107:00 am -
2 stops11h 18m
Deal found 9/20![Delta logo]()
$435
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/285:45 am -
1 stop7h 00m
Wed 11/42:40 pm -
1 stop8h 40m
Deal found 9/22![Southwest logo]()
$492
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 -
1 stop6h 28m
Wed 11/43:57 pm -
1 stop8h 36m
Deal found 9/18![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
1 stop6h 28m
Tue 11/38:35 pm -
2 stops16h 08m
Deal found 9/17![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/316:04 am -
1 stop6h 26m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 9/20![Delta logo]()
$470
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 September 22, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/147:25 am -
2 stops26h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$185
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/165:13 pm -
1 stop17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$198
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$198
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/159:30 am -
2 stops24h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/196:15 am -
2 stops34h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/196:15 am -
2 stops29h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/206:21 am -
2 stops33h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/232:28 pm -
2 stops16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/228:42 pm -
2 stops34h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/136:21 am -
2 stops29h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$233
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 1/126:00 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$243
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 9/277:01 pm -
2 stops17h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$249
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $430 (Delta) |
One-way from | $185 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $407 |
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 7,457,451 searches. Data last updated September 22, 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 Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/16
1:31 pm-12:28 pm
2 stops20h 57m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Fri 1/1
6:30 pm-2:25 pm
1 stop17h 55m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Mon 2/1
6:00 am-11:50 pm
2 stops15h 50m
Santiago de los Caballeros
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
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
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$198
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Thu 12/31
9:30 am-12:34 pm
2 stops25h 04m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$204
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Wed 1/6
5:25 pm-1:30 pm
2 stops18h 05m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$238
Quickest round-trip
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Tue 1/12
6:00 am-2:15 pm
1 stop6h 15m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$243
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sun 9/27
7:01 pm-1:27 pm
2 stops17h 26m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$249
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 11/14
7:25 am-7:18 pm
3 stops33h 53m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$250
ChicagoSanto Domingo
MDW Chicago Midway - SDQ Santo Domingo Las Americas
MDWSDQ
Chicago Midway
Sat 10/3
6:05 am-1:27 pm
1 stop6h 22m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$281
Showing 1-10 of 49 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $364). 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.
How often are flights from Chicago to the Dominican Republic delayed?
About 39% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 90 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 39% 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 September 22, 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.
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 22, 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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$478 | Average$1,001 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$503 | Average$860 | FlexibilityNo cancel fee | On-time63% |