$122+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Apr 25 — May 21
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
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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 March 26, 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 March 26, 2026.
This Frontier deal was found by Cheapflights users on 3/24. 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.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Thu 4/162:20 pm
PUJ
- MDW
2 stops18h 39m
Frontier
Deal found 3/24![Frontier logo]()
$296
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- PUJ
1 stop27h 07m
Frontier
Wed 4/159:13 pm
PUJ
- MDW
2 stops26h 06m
Frontier
Deal found 3/24![Frontier logo]()
$303
This Priceline deal was found by Cheapflights users on 3/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Thu 5/79:29 pm
PUJ
- MDW
2 stops38h 35m
Frontier
Deal found 3/23![Frontier logo]()
$304
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Fri 4/171:37 pm
PUJ
- MDW
2 stops27h 23m
Frontier
Deal found 3/24![Frontier logo]()
$306
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 pm
MDW
- PUJ
1 stop22h 39m
Frontier
Fri 5/11:37 pm
PUJ
- MDW
2 stops9h 49m
Frontier
Deal found 3/24![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 3/24. 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 4/187:34 pm
MDW
- PUJ
2 stops16h 36m
Frontier
Sat 5/212:02 pm
PUJ
- MDW
2 stops20h 39m
Frontier
Deal found 3/24![Frontier logo]()
$308
This Justfly.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- PUJ
1 stop23h 43m
Frontier
Tue 4/219:13 pm
PUJ
- MDW
2 stops35h 13m
Frontier
Deal found 3/26![Frontier logo]()
$310
This Justfly.com deal was found by Cheapflights users on 3/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Wed 5/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 3/24![Frontier logo]()
$311
This FlightHub deal was found by Cheapflights users on 3/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Mon 5/113:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 3/23![Frontier logo]()
$312
This FlightHub deal was found by Cheapflights users on 3/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:30 am
MDW
- PUJ
1 stop29h 18m
Frontier
Fri 4/171:37 pm
PUJ
- MDW
2 stops27h 23m
Frontier
Deal found 3/25![Frontier logo]()
$313
This FlightHub deal was found by Cheapflights users on 3/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- PUJ
1 stop23h 09m
Frontier
Sat 5/93:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 3/25![Frontier logo]()
$318
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:00 am
MDW
- SDQ
1 stop7h 53m
Frontier
Mon 4/134:08 pm
SDQ
- MDW
1 stop28h 23m
Frontier
Deal found 3/24![Frontier logo]()
$331
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 March 26, 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 March 26, 2026.
This Delta deal was found by Cheapflights users on 3/24. 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 4/187:16 pm
MDW
- PUJ
1 stop18h 13m
Delta
Thu 4/302:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 3/24![Delta logo]()
$459
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:35 am
MDW
- PUJ
1 stop6h 30m
Southwest
Sat 4/2512:55 pm
PUJ
- MDW
Nonstop5h 00m
Southwest
Deal found 3/25![Southwest logo]()
$472
This Delta deal was found by Cheapflights users on 3/21. 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 4/146:00 am
MDW
- SDQ
1 stop6h 12m
Delta
Wed 4/292:37 pm
SDQ
- MDW
1 stop8h 51m
Delta
Deal found 3/21![Delta logo]()
$481
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/256:00 am
MDW
- SDQ
1 stop6h 12m
Delta
Sat 5/22:37 pm
SDQ
- MDW
1 stop8h 51m
Delta
Deal found 3/26![Delta logo]()
$481
This Southwest deal was found by Cheapflights users on 3/21. 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 9/145:00 am
MDW
- PUJ
1 stop7h 40m
Southwest
Fri 9/251:45 pm
PUJ
- MDW
1 stop9h 55m
Southwest
Deal found 3/21![Southwest logo]()
$553
This Delta deal was found by Cheapflights users on 3/21. 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 5/51:24 pm
MDW
- SDQ
2 stops9h 53m
Delta
Tue 5/126:05 am
SDQ
- MDW
2 stops13h 28m
Delta
Deal found 3/21![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 3/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:30 am
MDW
- PUJ
1 stop6h 30m
Southwest
Sat 5/912:55 pm
PUJ
- MDW
Nonstop5h 00m
Southwest
Deal found 3/24![Southwest logo]()
$554
This Delta deal was found by Cheapflights users on 3/23. 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 4/219:27 am
MDW
- SDQ
2 stops13h 50m
Delta
Tue 4/282:37 pm
SDQ
- MDW
1 stop8h 51m
Delta
Deal found 3/23![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 3/24. 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 4/206:00 am
MDW
- SDQ
1 stop6h 12m
Delta
Sat 4/256:05 am
SDQ
- MDW
2 stops12h 53m
Delta
Deal found 3/24![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 3/22. 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.
Mon 9/75:00 am
MDW
- PUJ
1 stop7h 40m
Southwest
Sun 9/132:50 pm
PUJ
- MDW
1 stop7h 30m
Southwest
Deal found 3/22![Southwest logo]()
$606
This Delta deal was found by Cheapflights users on 3/21. 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 5/211:18 am
MDW
- SDQ
2 stops11h 59m
Delta
Sat 5/92:48 pm
SDQ
- MDW
1 stop7h 21m
Delta
Deal found 3/21![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:40 am
MDW
- PUJ
Nonstop4h 20m
Southwest
Sat 5/1612:55 pm
PUJ
- MDW
Nonstop5h 00m
Southwest
Deal found 3/25![Southwest logo]()
$608
This Delta deal was found by Cheapflights users on 3/23. 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.
Sat 5/211:18 am
MDW
- STI
2 stops12h 04m
Delta
Sat 5/96:00 am
STI
- MDW
2 stops12h 56m
Delta
Deal found 3/23![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:10 pm
MDW
- PUJ
2 stops18h 05m
Southwest
Wed 8/121:45 pm
PUJ
- MDW
2 stops9h 05m
Southwest
Deal found 3/25![Southwest logo]()
$623
This Delta deal was found by Cheapflights users on 3/23. 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 8/186:00 am
MDW
- PUJ
1 stop7h 51m
Delta
Wed 8/262:52 pm
PUJ
- MDW
1 stop7h 54m
Delta
Deal found 3/23![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 3/22. 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 9/26:00 am
MDW
- PUJ
1 stop6h 27m
Delta
Sat 9/51:05 pm
PUJ
- MDW
1 stop9h 41m
Delta
Deal found 3/22![Delta logo]()
$542
This Delta deal was found by Cheapflights users on 3/22. 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 5/66:00 am
MDW
- STI
2 stops12h 33m
Delta
Wed 5/136:00 am
STI
- MDW
2 stops13h 33m
Delta
Deal found 3/22![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 3/21. 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 9/146:00 am
MDW
- PUJ
1 stop7h 32m
Delta
Wed 9/232:45 pm
PUJ
- MDW
1 stop8h 01m
Delta
Deal found 3/21![Delta logo]()
$573
This Delta deal was found by Cheapflights users on 3/23. 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 7/316:58 pm
MDW
- PUJ
2 stops15h 45m
Delta
Sat 8/82:50 pm
PUJ
- MDW
2 stops19h 18m
Delta
Deal found 3/23![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 3/23. 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 4/129:30 am
MDW
- PUJ
2 stops25h 48m
Delta
Wed 4/153:57 pm
PUJ
- MDW
2 stops17h 50m
Delta
Deal found 3/23![Delta logo]()
$648
This Delta deal was found by Cheapflights users on 3/24. 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.
Fri 5/86:23 am
MDW
- STI
2 stops12h 05m
Delta
Fri 5/156:00 am
STI
- MDW
2 stops13h 33m
Delta
Deal found 3/24![Delta logo]()
$1,290
This Delta deal was found by Cheapflights users on 3/25. 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.
Thu 4/99:30 am
MDW
- STI
2 stops13h 24m
Delta
Mon 4/138:59 pm
STI
- MDW
2 stops16h 08m
Delta
Deal found 3/25![Delta logo]()
$3,436
Last-minute flights from Midway to Dominican RepublicDiscover last-minute flight deals from Midway to Dominican Republic. Data last updated March 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Dominican Republic. Data last updated March 26, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:00 am
MDW
- SDQ
1 stop7h 53m
Frontier
Mon 4/134:08 pm
SDQ
- MDW
1 stop28h 23m
Frontier
Deal found 3/24![Frontier logo]()
$331
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- PUJ
1 stop27h 07m
Frontier
Wed 4/159:13 pm
PUJ
- MDW
2 stops26h 06m
Frontier
Deal found 3/24![Frontier logo]()
$303
This Expedia deal was found by Cheapflights users on 3/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- SDQ
1 stop7h 53m
Frontier
Sat 4/113:45 pm
SDQ
- MDW
1 stop8h 20m
Frontier
Deal found 3/21![Frontier logo]()
$355
This FlightHub deal was found by Cheapflights users on 3/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:30 am
MDW
- PUJ
1 stop29h 18m
Frontier
Fri 4/171:37 pm
PUJ
- MDW
2 stops27h 23m
Frontier
Deal found 3/25![Frontier logo]()
$313
This Frontier deal was found by Cheapflights users on 3/24. 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.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Thu 4/162:20 pm
PUJ
- MDW
2 stops18h 39m
Frontier
Deal found 3/24![Frontier logo]()
$296
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Fri 4/171:37 pm
PUJ
- MDW
2 stops27h 23m
Frontier
Deal found 3/24![Frontier logo]()
$306
This FlightHub deal was found by Cheapflights users on 3/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 pm
MDW
- PUJ
1 stop22h 39m
Frontier
Fri 5/11:37 pm
PUJ
- MDW
2 stops9h 49m
Frontier
Deal found 3/24![Frontier logo]()
$307
This Justfly.com deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- PUJ
1 stop23h 43m
Frontier
Tue 4/219:13 pm
PUJ
- MDW
2 stops35h 13m
Frontier
Deal found 3/26![Frontier logo]()
$310
This Justfly.com deal was found by Cheapflights users on 3/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 pm
MDW
- PUJ
1 stop22h 39m
Frontier
Tue 5/53:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Deal found 3/24![Frontier logo]()
$318
This Frontier deal was found by Cheapflights users on 3/24. 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 4/187:34 pm
MDW
- PUJ
2 stops16h 36m
Frontier
Sat 5/212:02 pm
PUJ
- MDW
2 stops20h 39m
Frontier
Deal found 3/24![Frontier logo]()
$308
This Justfly.com deal was found by Cheapflights users on 3/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Wed 5/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 3/24![Frontier logo]()
$311
This FlightHub deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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.
Sat 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Sat 4/253:04 pm
PUJ
- MDW
1 stop19h 54m
Frontier
Deal found 3/26![Frontier logo]()
$312
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 March 26, 2026.
Search for one-way flight options from Midway to Dominican Republic. Find affordable one-way fares based on user searches. Data last updated March 26, 2026.
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:30 am
MDW
- SDQ
1 stop6h 26m
Frontier
Deal found 3/25![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
- SDQ
1 stop7h 53m
Frontier
Deal found 3/25![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 3/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- SDQ
1 stop28h 02m
Frontier
Deal found 3/25![Frontier logo]()
$138
This Super.com deal was found by Cheapflights users on 3/23. 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.
Sat 4/256:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Deal found 3/23![Frontier logo]()
$155
This Frontier deal was found by Cheapflights users on 3/24. 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 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Deal found 3/24![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- PUJ
2 stops30h 10m
Frontier
Deal found 3/25![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:10 am
MDW
- SDQ
2 stops30h 19m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 pm
MDW
- PUJ
2 stops18h 42m
Frontier
Deal found 3/25![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:15 pm
MDW
- SDQ
2 stops22h 14m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MDW
- SDQ
2 stops30h 29m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$174
This Priceline deal was found by Cheapflights users on 3/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:15 pm
MDW
- PUJ
1 stop22h 39m
Frontier
Deal found 3/25![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 3/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:30 am
MDW
- PUJ
1 stop6h 30m
Southwest
Deal found 3/24![Southwest logo]()
$180
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 March 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Frontier) |
One-way from | $122 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $601 |
Good round-trip deal | $571 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 March 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 4/18
7:16 pm-2:29 pm
1 stop18h 13m
Punta Cana
Thu 4/30
2:46 pm-10:28 pm
1 stop8h 42m
$459
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 4/20
5:35 am-1:05 pm
1 stop6h 30m
Punta Cana
Sat 4/25
12:55 pm-4:55 pm
Nonstop5h 00m
$472
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Tue 4/14
6:00 am-1:12 pm
1 stop6h 12m
Santo Domingo Las Americas
Wed 4/29
2:37 pm-10:28 pm
1 stop8h 51m
$481
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 4/25
6:00 am-1:12 pm
1 stop6h 12m
Santo Domingo Las Americas
Sat 5/2
2:37 pm-10:28 pm
1 stop8h 51m
$481
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Tue 5/5
1:24 pm-12:17 am
2 stops9h 53m
Santo Domingo Las Americas
Tue 5/12
6:05 am-6:33 pm
2 stops13h 28m
$485
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Tue 4/21
9:27 am-12:17 am
2 stops13h 50m
Santo Domingo Las Americas
Tue 4/28
2:37 pm-10:28 pm
1 stop8h 51m
$485
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Mon 4/20
6:00 am-1:12 pm
1 stop6h 12m
Santo Domingo Las Americas
Sat 4/25
6:05 am-5:58 pm
2 stops12h 53m
$485
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 5/2
11:18 am-12:17 am
2 stops11h 59m
Santo Domingo Las Americas
Sat 5/9
2:48 pm-9:09 pm
1 stop7h 21m
$485
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Sat 5/2
11:18 am-12:22 am
2 stops12h 04m
Santiago de los Caballeros
Sat 5/9
6:00 am-5:56 pm
2 stops12h 56m
$493
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 8/18
6:00 am-2:51 pm
1 stop7h 51m
Punta Cana
Wed 8/26
2:52 pm-9:46 pm
1 stop7h 54m
$507
Showing 1-10 of 43 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $252). Flying from Chicago Midway Airport to Dominican Republic in December is currently the most expensive (average of $863). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to DO?
Find hourly flight availability from Midway to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 26, 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 24% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 109 minutes.
What is the most punctual flight time for Chicago to the Dominican Republic flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to the Dominican Republic flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 24% 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 March 26, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to the Dominican Republic, such as Southwest,Delta, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Dominican Republic. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Dominican Republic
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Dominican Republic by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Dominican Republic by cabin class
Find flights from Midway to Dominican Republic, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Dominican Republic flights
Browse other Midway and Dominican Republic flight options. Last updated on March 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Dominican Republic regions
Consider these flights traveling to Dominican Republic regions.
Top 3 airlines flying from Midway to Dominican Republic
Discover the top 3 airlines that operate flights from Midway to Dominican Republic. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$418 | Average$659 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$539 | Average$779 | FlexibilityNo cancel fee | On-timeN/A |