$182+ Cheap flights from Midway (MDW) to the Dominican Republic
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Jul 25 — Aug 11
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Dominican Republic with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Dominican Republic
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Cheapest flights from Midway to Dominican RepublicExplore the most affordable flight options available from Midway to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 25, 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 June 25, 2026.
This Delta deal was found by Cheapflights users on 6/21. 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 8/156:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 8/222:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/21![Delta logo]()
$388
This Delta deal was found by Cheapflights users on 6/22. 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.
Tue 8/116:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Tue 8/182:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/22![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/46:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Fri 9/112:53 pm
SDQ
- MDW
1 stop8h 52m
Delta
Deal found 6/23![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/16:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Tue 9/152:53 pm
SDQ
- MDW
2 stops22h 46m
Delta
Deal found 6/24![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 6/20. 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 8/156:05 am
MDW
- SDQ
2 stops17h 49m
Delta
Fri 8/212:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/20![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 6/22. 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 8/126:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Mon 8/172:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/22![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/245:00 am
MDW
- PUJ
1 stop7h 40m
Southwest
Thu 8/272:35 pm
PUJ
- MDW
1 stop7h 25m
Southwest
Deal found 6/23![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/36:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 9/192:53 pm
SDQ
- MDW
1 stop8h 52m
Delta
Deal found 6/24![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/36:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Wed 9/162:53 pm
SDQ
- MDW
2 stops19h 14m
Delta
Deal found 6/24![Delta logo]()
$439
This CheapOair deal was found by Cheapflights users on 6/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/43:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/22![Frontier logo]()
$458
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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
MDW
- SDQ
1 stop6h 23m
Delta
Tue 9/152:53 pm
SDQ
- MDW
1 stop8h 52m
Delta
Deal found 6/23![Delta logo]()
$460
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/1511:06 am
MDW
- PUJ
1 stop26h 15m
Frontier
Sat 8/223:37 pm
PUJ
- MDW
1 stop20h 18m
Frontier
Deal found 6/24![Frontier logo]()
$470
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 June 25, 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 June 25, 2026.
This Delta deal was found by Cheapflights users on 6/21. 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 8/156:05 am
MDW
- SDQ
2 stops17h 49m
Delta
Fri 8/212:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/21![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 6/22. 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.
Thu 8/277:55 pm
MDW
- PUJ
2 stops16h 45m
Southwest
Fri 9/41:45 pm
PUJ
- MDW
2 stops9h 10m
Southwest
Deal found 6/22![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/126:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Mon 8/172:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/24![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/1710:48 am
MDW
- STI
2 stops24h 38m
Delta
Wed 9/307:30 pm
STI
- MDW
2 stops14h 37m
Delta
Deal found 6/24![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 6/22. 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.
Sun 9/66:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Tue 9/152:53 pm
SDQ
- MDW
1 stop8h 52m
Delta
Deal found 6/22![Delta logo]()
$510
This Southwest deal was found by Cheapflights users on 6/21. 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 7/268:20 pm
MDW
- PUJ
2 stops17h 10m
Southwest
Thu 7/301:45 pm
PUJ
- MDW
2 stops11h 25m
Southwest
Deal found 6/21![Southwest logo]()
$768
This Southwest deal was found by Cheapflights users on 6/22. 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.
Fri 7/248:50 pm
MDW
- PUJ
2 stops15h 40m
Southwest
Sat 8/12:15 pm
PUJ
- MDW
1 stop9h 15m
Southwest
Deal found 6/22![Southwest logo]()
$780
This Delta deal was found by Cheapflights users on 6/20. 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 8/56:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Wed 8/196:05 am
SDQ
- MDW
2 stops13h 28m
Delta
Deal found 6/20![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 6/22. 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 12/99:30 am
MDW
- SDQ
2 stops14h 05m
Delta
Wed 12/166:45 am
SDQ
- MDW
2 stops13h 52m
Delta
Deal found 6/22![Delta logo]()
$650
This Delta deal was found by Cheapflights users on 6/22. 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.
Fri 8/146:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Fri 8/212:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/22![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 12/106:00 am
MDW
- PUJ
1 stop7h 40m
Delta
Wed 12/163:50 pm
PUJ
- MDW
1 stop8h 20m
Delta
Deal found 6/23![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/46:42 pm
MDW
- PUJ
2 stops16h 01m
Delta
Thu 8/64:04 pm
PUJ
- MDW
2 stops18h 13m
Delta
Deal found 6/23![Delta logo]()
$675
This Delta deal was found by Cheapflights users on 6/21. 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 8/306:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Tue 9/82:53 pm
SDQ
- MDW
1 stop8h 52m
Delta
Deal found 6/21![Delta logo]()
$690
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:05 am
MDW
- PUJ
1 stop7h 34m
Delta
Sat 9/124:00 pm
PUJ
- MDW
1 stop7h 45m
Delta
Deal found 6/25![Delta logo]()
$691
This Delta deal was found by Cheapflights users on 6/21. 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 8/96:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 8/152:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/21![Delta logo]()
$736
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:05 am
MDW
- PUJ
1 stop6h 20m
Delta
Tue 10/132:49 pm
PUJ
- MDW
1 stop8h 21m
Delta
Deal found 6/24![Delta logo]()
$750
This Delta deal was found by Cheapflights users on 6/21. 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 8/306:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sun 9/62:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/21![Delta logo]()
$802
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 10/106:00 am
MDW
- PUJ
1 stop6h 24m
Delta
Tue 10/133:56 pm
PUJ
- MDW
1 stop7h 14m
Delta
Deal found 6/24![Delta logo]()
$869
This Delta deal was found by Cheapflights users on 6/20. 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.
Tue 8/256:05 am
MDW
- PUJ
1 stop6h 20m
Delta
Mon 8/312:50 pm
PUJ
- MDW
1 stop8h 46m
Delta
Deal found 6/20![Delta logo]()
$905
This Delta deal was found by Cheapflights users on 6/22. 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.
Thu 8/612:46 pm
MDW
- STI
2 stops12h 09m
Delta
Thu 8/138:59 pm
STI
- MDW
2 stops20h 16m
Delta
Deal found 6/22![Delta logo]()
$3,352
This Delta deal was found by Cheapflights users on 6/22. 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.
Sun 7/266:00 am
MDW
- STI
2 stops12h 34m
Delta
Sun 8/28:59 pm
STI
- MDW
2 stops20h 16m
Delta
Deal found 6/22![Delta logo]()
$4,313
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated June 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated June 25, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:11 pm
MDW
- SDQ
2 stops45h 52m
Frontier
Mon 7/1312:18 pm
SDQ
- MDW
2 stops47h 49m
Frontier
Deal found 6/24![Frontier logo]()
$762
This Priceline deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 7/213:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/24![Frontier logo]()
$498
This Priceline deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 7/213:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/24![Frontier logo]()
$478
This Frontier deal was found by Cheapflights users on 6/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Wed 7/2211:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/21![Frontier logo]()
$489
This CheapOair deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Mon 7/206:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Sat 7/253:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/24![Frontier logo]()
$499
This Priceline deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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.
Fri 7/2412:11 pm
MDW
- PUJ
1 stop25h 10m
Frontier
Sat 8/13:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/24![Frontier logo]()
$527
This Gotogate deal was found by Cheapflights users on 6/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:11 pm
MDW
- PUJ
1 stop25h 10m
Frontier
Sat 8/13:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/22![Frontier logo]()
$506
This Gotogate deal was found by Cheapflights users on 6/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Mon 8/33:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/22![Frontier logo]()
$518
This CheapOair deal was found by Cheapflights users on 6/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/43:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/22![Frontier logo]()
$458
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/286:00 am
MDW
- SDQ
1 stop6h 17m
Delta
Tue 8/42:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/23![Delta logo]()
$649
This CheapOair deal was found by Cheapflights users on 6/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:11 pm
MDW
- PUJ
1 stop25h 10m
Frontier
Tue 8/43:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/22![Frontier logo]()
$507
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/316:00 am
MDW
- SDQ
1 stop6h 17m
Delta
Fri 8/72:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/23![Delta logo]()
$726
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 June 25, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated June 25, 2026.
This Delta deal was found by Cheapflights users on 6/21. 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 10/206:00 am
MDW
- SDQ
2 stops11h 24m
Delta
Deal found 6/21![Delta logo]()
$182
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/286:00 am
MDW
- SDQ
1 stop6h 17m
Delta
Deal found 6/24![Delta logo]()
$187
This Frontier deal was found by Cheapflights users on 6/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/20![Frontier logo]()
$204
This Trip.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/23![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Wed 8/126:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/23![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 6/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/21![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Fri 8/76:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/23![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/24![Frontier logo]()
$228
This Booking.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/23![Frontier logo]()
$230
This Booking.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/24![Frontier logo]()
$236
This Delta deal was found by Cheapflights users on 6/22. 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.
Tue 8/46:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Deal found 6/22![Delta logo]()
$263
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/16:00 am
MDW
- SDQ
1 stop6h 17m
Delta
Deal found 6/24![Delta logo]()
$268
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 June 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $388 (Delta) |
One-way from | $182 (Delta) |
Popular in | June |
Cheapest in | September |
Average price | $661 |
Good round-trip deal | $583 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 June 25, 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
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 8/15
6:05 am-12:54 am
2 stops17h 49m
Santo Domingo Las Americas
Fri 8/21
2:53 pm-10:36 pm
1 stop8h 43m
$415
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Wed 8/12
6:05 am-6:06 pm
2 stops11h 01m
Santo Domingo Las Americas
Mon 8/17
2:53 pm-10:36 pm
1 stop8h 43m
$439
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Thu 9/17
10:48 am-12:26 pm
2 stops24h 38m
Santiago de los Caballeros
Wed 9/30
7:30 pm-9:07 am
2 stops14h 37m
$495
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sun 9/6
6:05 am-6:06 pm
2 stops11h 01m
Santo Domingo Las Americas
Tue 9/15
2:53 pm-10:45 pm
1 stop8h 52m
$510
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 8/27
7:55 pm-1:40 pm
2 stops16h 45m
Punta Cana
Fri 9/4
1:45 pm-9:55 pm
2 stops9h 10m
$611
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Wed 8/5
6:05 am-1:28 pm
1 stop6h 23m
Santo Domingo Las Americas
Wed 8/19
6:05 am-6:33 pm
2 stops13h 28m
$649
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Wed 12/9
9:30 am-1:35 am
2 stops14h 05m
Santo Domingo Las Americas
Wed 12/16
6:45 am-6:37 pm
2 stops13h 52m
$650
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Fri 8/14
6:05 am-6:06 pm
2 stops11h 01m
Santo Domingo Las Americas
Fri 8/21
2:53 pm-10:36 pm
1 stop8h 43m
$656
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 12/10
6:00 am-3:40 pm
1 stop7h 40m
Punta Cana
Wed 12/16
3:50 pm-10:10 pm
1 stop8h 20m
$671
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 8/4
6:42 pm-11:43 am
2 stops16h 01m
Punta Cana
Thu 8/6
4:04 pm-9:17 am
2 stops18h 13m
$675
Showing 1-10 of 42 resultsSorted by cheapest first
Best time to book a flight from Midway to Dominican Republic
Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Midway with our price prediction graph.
MDW-PUJ
MDW-SDQ
MDW-STI
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to the Dominican Republic
MDW-DO0
MDW-PUJ
MDW-SDQ
MDW-STI
What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $190). Flying from Chicago Midway Airport to Dominican Republic in December is currently the most expensive (average of $860). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to DO?
Find hourly flight availability from Midway to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 25, 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 26% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 96 minutes.
What is the most punctual flight time for Chicago to the Dominican Republic flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to the Dominican Republic flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 26% 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 June 25, 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.
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 June 25, 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 June 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$464 | Average$869 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$503 | Average$980 | FlexibilityNo cancel fee | On-time63% |