$198+ Cheap flights from Midway (MDW) to Punta Cana (PUJ)
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Punta Cana 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 Punta Cana
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Cheapest flights from Midway to Punta CanaExplore the most affordable flight options available from Midway to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
Explore the most affordable flight options available from Midway to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$447
This CheapOair deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 9/16:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Tue 9/83:39 pm
PUJ
- MDW
1 stop20h 19m
Frontier
Deal found 6/7![Frontier logo]()
$458
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Wed 7/2211:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$461
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/206:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$467
This CheapOair deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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.
Fri 8/146:05 am
MDW
- PUJ
2 stops27h 19m
Frontier
Sat 8/153:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/9![Frontier logo]()
$468
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Sat 7/113:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/6![Frontier logo]()
$470
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/9![Frontier logo]()
$472
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Wed 7/83:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/8![Frontier logo]()
$478
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/46:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Mon 8/103:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/10![Frontier logo]()
$479
This Priceline deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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.
Thu 8/1311:06 am
MDW
- PUJ
1 stop26h 15m
Frontier
Tue 8/183:39 pm
PUJ
- MDW
1 stop20h 30m
Frontier
Deal found 6/9![Frontier logo]()
$487
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/16:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Sat 8/83:31 pm
PUJ
- MDW
1 stop19h 20m
Frontier
Deal found 6/9![Frontier logo]()
$489
Best flights from Midway to Punta CanaDiscover carefully curated flight deals from Midway to Punta Cana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
Discover carefully curated flight deals from Midway to Punta Cana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:00 am
MDW
- PUJ
1 stop7h 40m
Southwest
Fri 9/251:45 pm
PUJ
- MDW
1 stop8h 45m
Southwest
Deal found 6/6![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 10/216:00 am
MDW
- PUJ
1 stop6h 24m
Delta
Sat 10/312:49 pm
PUJ
- MDW
1 stop8h 21m
Delta
Deal found 6/10![Delta logo]()
$600
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:55 pm
MDW
- PUJ
2 stops16h 25m
Southwest
Fri 10/21:25 pm
PUJ
- MDW
1 stop8h 50m
Southwest
Deal found 6/6![Southwest logo]()
$571
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/146:00 am
MDW
- PUJ
1 stop7h 40m
Delta
Sat 11/213:50 pm
PUJ
- MDW
1 stop8h 20m
Delta
Deal found 6/8![Delta logo]()
$673
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am
MDW
- PUJ
1 stop6h 05m
Southwest
Sun 10/43:20 pm
PUJ
- MDW
1 stop10h 05m
Southwest
Deal found 6/7![Southwest logo]()
$633
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:30 am
MDW
- PUJ
1 stop6h 55m
Southwest
Sat 7/1111:50 am
PUJ
- MDW
2 stops12h 55m
Southwest
Deal found 6/6![Southwest logo]()
$633
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/187:55 pm
MDW
- PUJ
2 stops16h 30m
Southwest
Tue 9/221:45 pm
PUJ
- MDW
1 stop8h 15m
Southwest
Deal found 6/9![Southwest logo]()
$638
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:55 pm
MDW
- PUJ
2 stops15h 50m
Southwest
Fri 10/301:25 pm
PUJ
- MDW
2 stops11h 45m
Southwest
Deal found 6/7![Southwest logo]()
$657
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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
MDW
- PUJ
1 stop7h 00m
Southwest
Sun 11/14:50 pm
PUJ
- MDW
1 stop8h 05m
Southwest
Deal found 6/7![Southwest logo]()
$695
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/98:55 pm
MDW
- PUJ
2 stops16h 35m
Southwest
Thu 7/161:45 pm
PUJ
- MDW
2 stops11h 25m
Southwest
Deal found 6/9![Southwest logo]()
$727
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 11/58:40 pm
MDW
- PUJ
2 stops16h 30m
Southwest
Mon 11/94:50 pm
PUJ
- MDW
2 stops18h 10m
Southwest
Deal found 6/10![Southwest logo]()
$732
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/2710:30 am
MDW
- PUJ
Nonstop4h 25m
Southwest
Mon 8/34:55 pm
PUJ
- MDW
1 stop8h 15m
Southwest
Deal found 6/7![Southwest logo]()
$734
Last-minute flights from Midway to Punta CanaDiscover last-minute flight deals from Midway to Punta Cana. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Punta Cana. Data last updated June 10, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Sat 7/113:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/6![Frontier logo]()
$470
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Wed 7/83:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/8![Frontier logo]()
$478
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/116:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Wed 7/2211:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/9![Frontier logo]()
$492
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/9![Frontier logo]()
$472
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/206:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$467
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/10![Frontier logo]()
$499
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$447
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Wed 7/2211:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$461
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/216:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Thu 7/2311:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/10![Frontier logo]()
$496
This Frontier deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/286:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Tue 8/411:46 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 6/9![Frontier logo]()
$501
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Wed 7/296:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Sat 8/13:31 pm
PUJ
- MDW
1 stop20h 36m
Frontier
Deal found 6/10![Frontier logo]()
$479
One-way flights from Midway to Punta CanaSearch for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
Search for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/156:15 am
MDW
- PUJ
1 stop6h 05m
Southwest
Deal found 6/10![Southwest logo]()
$198
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/86:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Deal found 6/10![Frontier logo]()
$208
This Justfly.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Tue 6/306:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Deal found 6/10![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/8![Frontier logo]()
$222
This Super.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/9![Frontier logo]()
$223
This Super.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.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 6/6![Frontier logo]()
$227
This Trip.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/6![Frontier logo]()
$233
This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/56:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/10![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/86:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/10![Frontier logo]()
$248
This Trip.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:05 am
MDW
- PUJ
1 stop7h 16m
Frontier
Deal found 6/6![Frontier logo]()
$254
Find flight deals from Midway to Punta Cana
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Punta Cana (PUJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $458 (CheapOair) |
One-way from | $198 (Southwest) |
Popular in | June |
Cheapest in | April |
Average price | $1,307 |
Good round-trip deal | $635 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Punta Cana 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 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 9/21
5:00 am-1:40 pm
1 stop7h 40m
Punta Cana
Fri 9/25
1:45 pm-9:30 pm
1 stop8h 45m
$566
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 9/28
7:55 pm-1:20 pm
2 stops16h 25m
Punta Cana
Fri 10/2
1:25 pm-9:15 pm
1 stop8h 50m
$571
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Wed 10/21
6:00 am-1:24 pm
1 stop6h 24m
Punta Cana
Sat 10/31
2:49 pm-10:10 pm
1 stop8h 21m
$600
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Wed 9/30
6:15 am-1:20 pm
1 stop6h 05m
Punta Cana
Sun 10/4
3:20 pm-12:25 am
1 stop10h 05m
$633
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 7/4
6:30 am-2:25 pm
1 stop6h 55m
Punta Cana
Sat 7/11
11:50 am-11:45 pm
2 stops12h 55m
$633
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 9/18
7:55 pm-1:25 pm
2 stops16h 30m
Punta Cana
Tue 9/22
1:45 pm-9:00 pm
1 stop8h 15m
$638
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 10/22
8:55 pm-1:45 pm
2 stops15h 50m
Punta Cana
Fri 10/30
1:25 pm-12:10 am
2 stops11h 45m
$657
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 11/14
6:00 am-3:40 pm
1 stop7h 40m
Punta Cana
Sat 11/21
3:50 pm-10:10 pm
1 stop8h 20m
$673
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 10/24
5:00 am-1:00 pm
1 stop7h 00m
Punta Cana
Sun 11/1
4:50 pm-10:55 pm
1 stop8h 05m
$695
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 7/9
8:55 pm-2:30 pm
2 stops16h 35m
Punta Cana
Thu 7/16
1:45 pm-12:10 am
2 stops11h 25m
$727
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Midway to Punta Cana
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Punta Cana in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Punta Cana flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Punta Cana flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Punta Cana flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Punta Cana flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Punta Cana flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Punta Cana
Have a flexible travel schedule? Discover the best time to fly to Punta Cana from Midway with our price prediction graph.
MDW-PUJ
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 Punta Cana
Prices
Delays
What is the cheapest month to book a flight from Chicago Midway Airport to Punta Cana?
Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $515). Flying from Chicago Midway Airport to Punta Cana in June is currently the most expensive (average of $1,307). 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 PUJ?
Find hourly flight availability from Midway to Punta Cana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 10, 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 Punta Cana as you normally would.
How often are flights from Chicago to Punta Cana delayed?
About 26% of weekly flights between Chicago and Punta Cana 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 Punta Cana 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 Punta Cana 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 Punta Cana
Get insights into the airlines that provide service to Punta Cana. 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 Punta Cana. Reviews last updated June 10, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from Chicago Midway Airport to Punta Cana by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Midway to Punta Cana. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Punta Cana?
Book flights to Punta Cana if you plan to visit one of these locationsBavaro
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Complete your trip
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Search flights from Midway to Punta Cana by cabin class
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Midway and Punta Cana flights
Browse other Midway and Punta Cana flight options. Last updated on June 10, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Punta Cana
Explore flights to Punta Cana departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
Top 2 airlines flying from Midway to Punta Cana
Discover the top 2 airlines that operate flights from Midway to Punta Cana. 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 10, 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% |