$168+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Jun 14 — Jun 211
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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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 May 15, 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 May 15, 2026.
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/286:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sat 8/83:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/11![Frontier logo]()
$392
This Gotogate deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Tue 7/286:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sun 8/23:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/12![Frontier logo]()
$397
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/26:00 am
MDW
- PUJ
2 stops27h 35m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/12![Frontier logo]()
$403
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Sat 8/293:39 pm
PUJ
- MDW
1 stop20h 33m
Frontier
Deal found 5/12![Frontier logo]()
$411
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Sun 8/96:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Sat 8/153:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/12![Frontier logo]()
$412
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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
Wed 7/811:46 am
PUJ
- MDW
2 stops11h 22m
Frontier
Deal found 5/12![Frontier logo]()
$415
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Sun 7/266:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Tue 8/43:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/11![Frontier logo]()
$417
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/256:00 am
MDW
- PUJ
1 stop7h 29m
Frontier
Sun 8/303:39 pm
PUJ
- MDW
1 stop20h 30m
Frontier
Deal found 5/12![Frontier logo]()
$418
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/2012:27 pm
MDW
- PUJ
1 stop24h 58m
Frontier
Mon 8/243:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/12![Frontier logo]()
$419
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Sun 7/126:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Wed 7/2211:46 am
PUJ
- MDW
2 stops11h 22m
Frontier
Deal found 5/12![Frontier logo]()
$421
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/312:04 pm
MDW
- PUJ
1 stop25h 26m
Frontier
Mon 7/63:44 pm
PUJ
- MDW
1 stop20h 23m
Frontier
Deal found 5/12![Frontier logo]()
$425
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/11![Frontier logo]()
$429
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 May 15, 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 May 15, 2026.
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 8/276:05 am
MDW
- PUJ
1 stop6h 20m
Delta
Fri 9/42:52 pm
PUJ
- MDW
1 stop7h 54m
Delta
Deal found 5/11![Delta logo]()
$620
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 10/45:20 am
MDW
- PUJ
1 stop8h 00m
Southwest
Fri 10/91:25 pm
PUJ
- MDW
1 stop12h 15m
Southwest
Deal found 5/15![Southwest logo]()
$649
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 5/266:23 am
MDW
- PUJ
1 stop7h 12m
Delta
Fri 6/52:50 pm
PUJ
- MDW
1 stop7h 19m
Delta
Deal found 5/15![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/48:40 am
MDW
- PUJ
Nonstop4h 25m
Southwest
Tue 8/111:45 pm
PUJ
- MDW
1 stop8h 15m
Southwest
Deal found 5/14![Southwest logo]()
$686
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 8/107:55 pm
MDW
- PUJ
2 stops16h 25m
Southwest
Fri 8/141:45 pm
PUJ
- MDW
2 stops18h 50m
Southwest
Deal found 5/15![Southwest logo]()
$703
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:05 am
MDW
- PUJ
1 stop7h 40m
Southwest
Tue 10/201:25 pm
PUJ
- MDW
1 stop8h 05m
Southwest
Deal found 5/14![Southwest logo]()
$727
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/24:20 pm
MDW
- PUJ
2 stops19h 05m
Southwest
Fri 7/101:25 pm
PUJ
- MDW
2 stops10h 35m
Southwest
Deal found 5/13![Southwest logo]()
$751
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/288:10 pm
MDW
- PUJ
2 stops17h 20m
Southwest
Sun 8/22:20 pm
PUJ
- MDW
2 stops11h 00m
Southwest
Deal found 5/14![Southwest logo]()
$768
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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
Mon 7/201:25 pm
PUJ
- MDW
2 stops10h 35m
Southwest
Deal found 5/14![Southwest logo]()
$778
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/308:10 pm
MDW
- PUJ
2 stops17h 20m
Southwest
Sat 7/114:50 pm
PUJ
- MDW
2 stops15h 20m
Southwest
Deal found 5/14![Southwest logo]()
$778
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 10/106:55 pm
MDW
- PUJ
2 stops17h 55m
Southwest
Tue 10/131:25 pm
PUJ
- MDW
2 stops9h 25m
Southwest
Deal found 5/13![Southwest logo]()
$783
This Southwest deal was found by Cheapflights users on 5/10. 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.
Fri 6/58:50 pm
MDW
- PUJ
2 stops15h 40m
Southwest
Sun 6/72:45 pm
PUJ
- MDW
1 stop9h 55m
Southwest
Deal found 5/10![Southwest logo]()
$790
Last-minute flights from Midway to Punta CanaDiscover last-minute flight deals from Midway to Punta Cana. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Punta Cana. Data last updated May 15, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 5/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Sun 5/313:35 pm
PUJ
- MDW
1 stop20h 34m
Frontier
Deal found 5/10![Frontier logo]()
$445
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Fri 5/296:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Tue 6/211:45 am
PUJ
- MDW
2 stops11h 17m
Frontier
Deal found 5/12![Frontier logo]()
$456
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/26:00 am
MDW
- PUJ
2 stops27h 35m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/12![Frontier logo]()
$403
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/26:00 am
MDW
- PUJ
2 stops27h 35m
Frontier
Sat 6/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/11![Frontier logo]()
$437
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Tue 6/93:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/11![Frontier logo]()
$429
This Priceline deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- PUJ
2 stops27h 57m
Frontier
Sat 6/63:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 5/11![Frontier logo]()
$443
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/611:59 am
MDW
- PUJ
1 stop25h 25m
Frontier
Sat 6/133:40 pm
PUJ
- MDW
1 stop20h 32m
Frontier
Deal found 5/12![Frontier logo]()
$440
This Frontier deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/66:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Wed 6/1011:42 am
PUJ
- MDW
2 stops11h 29m
Frontier
Deal found 5/14![Frontier logo]()
$454
This Frontier deal was found by Cheapflights users on 5/10. 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 6/166:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Wed 7/811:46 am
PUJ
- MDW
2 stops11h 22m
Frontier
Deal found 5/10![Frontier logo]()
$441
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/166:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Tue 6/233:56 pm
PUJ
- MDW
1 stop20h 13m
Frontier
Deal found 5/12![Frontier logo]()
$458
This Priceline deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/306:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Sun 7/53:59 pm
PUJ
- MDW
1 stop20h 08m
Frontier
Deal found 5/12![Frontier logo]()
$438
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 May 15, 2026.
Search for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/46:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/12![Frontier logo]()
$168
This FlightHub deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/306:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Deal found 5/12![Frontier logo]()
$170
This Trip.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/286:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/13![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/86:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Deal found 5/12![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Sun 8/26:00 am
MDW
- PUJ
1 stop7h 49m
Frontier
Deal found 5/12![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/46:00 am
MDW
- PUJ
1 stop7h 30m
Frontier
Deal found 5/11![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/56:00 am
MDW
- PUJ
1 stop7h 34m
Frontier
Deal found 5/12![Frontier logo]()
$188
This Mytrip deal was found by Cheapflights users on 5/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
MDW
- PUJ
1 stop7h 24m
Frontier
Deal found 5/10![Frontier logo]()
$198
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Tue 6/96:00 am
MDW
- PUJ
1 stop7h 46m
Frontier
Deal found 5/12![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/1112:11 pm
MDW
- PUJ
2 stops21h 25m
Frontier
Deal found 5/12![Frontier logo]()
$202
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 May 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $392 (Priceline) |
One-way from | $168 (Frontier) |
Popular in | March |
Cheapest in | October |
Average price | $853 |
Good round-trip deal | $605 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 May 15, 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
Thu 8/27
6:05 am-1:25 pm
1 stop6h 20m
Punta Cana
Fri 9/4
2:52 pm-9:46 pm
1 stop7h 54m
$620
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 10/4
5:20 am-2:20 pm
1 stop8h 00m
Punta Cana
Fri 10/9
1:25 pm-12:40 am
1 stop12h 15m
$649
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 5/26
6:23 am-2:35 pm
1 stop7h 12m
Punta Cana
Fri 6/5
2:50 pm-9:09 pm
1 stop7h 19m
$685
Quickest round-trip
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 7/4
8:40 am-2:05 pm
Nonstop4h 25m
Punta Cana
Tue 8/11
1:45 pm-9:00 pm
1 stop8h 15m
$686
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 8/10
7:55 pm-1:20 pm
2 stops16h 25m
Punta Cana
Fri 8/14
1:45 pm-7:35 am
2 stops18h 50m
$703
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 10/12
5:05 am-1:45 pm
1 stop7h 40m
Punta Cana
Tue 10/20
1:25 pm-8:30 pm
1 stop8h 05m
$727
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 7/2
4:20 pm-12:25 pm
2 stops19h 05m
Punta Cana
Fri 7/10
1:25 pm-11:00 pm
2 stops10h 35m
$751
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 7/28
8:10 pm-2:30 pm
2 stops17h 20m
Punta Cana
Sun 8/2
2:20 pm-12:20 am
2 stops11h 00m
$768
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 7/9
8:55 pm-2:30 pm
2 stops16h 35m
Punta Cana
Mon 7/20
1:25 pm-11:00 pm
2 stops10h 35m
$778
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/30
8:10 pm-2:30 pm
2 stops17h 20m
Punta Cana
Sat 7/11
4:50 pm-7:10 am
2 stops15h 20m
$778
Showing 1-10 of 19 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 May.
| 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $482). Flying from Chicago Midway Airport to Punta Cana in March is currently the most expensive (average of $1,125). 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 May 15, 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 25% 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 25% 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 May 15, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andFrontier 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.
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
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 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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Midway and Punta Cana flights
Browse other Midway and Punta Cana flight options. Last updated on May 15, 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 May 15, 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 May 15, 2026.
Top 3 airlines flying from Midway to Punta Cana
Discover the top 3 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 May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$416 | Average$666 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$539 | Average$779 | FlexibilityNo cancel fee | On-timeN/A |