$183+ Cheap flights from Midway (MDW) to Punta Cana (PUJ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Nov 19 — Nov 261
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 October 20, 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 October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:10 am -
1 stop8h 40m
Thu 11/124:50 pm -
1 stop8h 10m
Deal found 10/16![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:44 pm -
2 stops15h 44m
Thu 11/123:53 pm -
2 stops22h 58m
Deal found 10/16![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:04 am -
1 stop6h 26m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 10/17![Delta logo]()
$440
This Mytrip deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
2 stops23h 12m
Sat 12/127:19 pm -
2 stops26h 23m
Deal found 10/18![Frontier logo]()
$442
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/285:25 am -
1 stop8h 35m
Thu 12/33:35 pm -
1 stop7h 55m
Deal found 10/15![Southwest logo]()
$460
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop7h 36m
Sun 11/15:05 pm -
1 stop7h 28m
Deal found 10/18![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/15. 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.
Mon 10/196:44 pm -
2 stops17h 46m
Thu 10/222:55 pm -
2 stops19h 37m
Deal found 10/15![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop6h 28m
Wed 11/183:53 pm -
1 stop9h 01m
Deal found 10/18![Delta logo]()
$480
This Mytrip deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:28 pm -
3 stops26h 33m
Sat 12/127:19 pm -
2 stops26h 23m
Deal found 10/18![Multiple Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 10/15. 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.
Fri 11/135:05 am -
1 stop8h 05m
Fri 11/204:50 pm -
1 stop8h 10m
Deal found 10/15![Southwest logo]()
$485
This FlightHub deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
2 stops34h 24m
Tue 11/244:28 pm -
1 stop17h 44m
Deal found 10/18![Frontier logo]()
$486
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:25 pm -
2 stops17h 25m
Thu 11/193:35 pm -
1 stop7h 55m
Deal found 10/18![Southwest logo]()
$490
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 October 20, 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 October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:25 am -
1 stop8h 35m
Thu 12/33:35 pm -
1 stop7h 55m
Deal found 10/16![Southwest logo]()
$460
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop7h 36m
Sun 11/15:05 pm -
1 stop7h 28m
Deal found 10/18![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop7h 30m
Tue 1/124:55 pm -
1 stop7h 15m
Deal found 10/17![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:10 am -
1 stop8h 40m
Sun 11/224:50 pm -
1 stop8h 10m
Deal found 10/18![Southwest logo]()
$565
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/296:00 am -
1 stop7h 30m
Sat 12/53:53 pm -
1 stop9h 01m
Deal found 10/16![Delta logo]()
$525
This Southwest deal was found by Cheapflights users on 10/15. 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 12/68:25 pm -
2 stops16h 15m
Fri 12/112:40 pm -
1 stop10h 25m
Deal found 10/15![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:04 am -
1 stop7h 36m
Sat 10/314:05 pm -
1 stop7h 28m
Deal found 10/16![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:04 am -
1 stop7h 36m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 10/18![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/56:00 am -
1 stop6h 20m
Tue 1/124:55 pm -
1 stop7h 15m
Deal found 10/14![Delta logo]()
$615
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:00 am -
1 stop6h 28m
Wed 12/164:55 pm -
1 stop7h 59m
Deal found 10/16![Delta logo]()
$615
Last-minute flights from Midway to Punta CanaDiscover last-minute flight deals from Midway to Punta Cana. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Punta Cana. Data last updated October 20, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/15. 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.
Mon 10/196:04 am -
1 stop6h 26m
Thu 10/224:05 pm -
2 stops18h 27m
Deal found 10/15![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 10/15. 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.
Mon 10/196:44 pm -
2 stops17h 46m
Wed 10/214:05 pm -
2 stops21h 42m
Deal found 10/15![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop7h 36m
Sun 11/15:05 pm -
1 stop7h 28m
Deal found 10/18![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:04 am -
1 stop7h 36m
Tue 10/274:05 pm -
1 stop7h 28m
Deal found 10/18![Delta logo]()
$500
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:04 am -
1 stop6h 26m
Wed 11/45:05 pm -
1 stop7h 28m
Deal found 10/17![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:10 am -
1 stop8h 40m
Thu 11/124:50 pm -
1 stop8h 10m
Deal found 10/16![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:44 pm -
2 stops15h 44m
Thu 11/123:53 pm -
2 stops22h 58m
Deal found 10/16![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:25 pm -
2 stops17h 25m
Thu 11/193:35 pm -
1 stop7h 55m
Deal found 10/18![Southwest logo]()
$490
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop6h 28m
Thu 11/194:55 pm -
1 stop7h 59m
Deal found 10/18![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 10/15. 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.
Fri 11/135:05 am -
1 stop8h 05m
Fri 11/204:50 pm -
1 stop8h 10m
Deal found 10/15![Southwest logo]()
$485
This FlightHub deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
2 stops34h 24m
Tue 11/244:28 pm -
1 stop17h 44m
Deal found 10/18![Frontier logo]()
$486
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 11/285:25 am -
1 stop8h 35m
Thu 12/33:35 pm -
1 stop7h 55m
Deal found 10/15![Southwest logo]()
$460
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 October 20, 2026.
Search for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$183
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:44 pm -
2 stops15h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:04 am -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
2 stops34h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:28 pm -
2 stops23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:08 am -
3 stops33h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:21 pm -
2 stops41h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:28 pm -
2 stops23h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$231
This Southwest deal was found by Cheapflights users on 10/15. 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 11/95:10 am -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:42 pm -
2 stops40h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$242
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 October 20, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $400 (Delta) |
One-way from | $183 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $654 |
Good round-trip deal | $844 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 7,457,451 searches. Data last updated October 20, 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 Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Tue 12/29
6:15 pm-12:27 pm
1 stop16h 12m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Tue 11/17
6:00 am-2:28 pm
1 stop6h 28m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Thu 12/31
9:30 am-1:16 pm
2 stops25h 46m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$189
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/9
6:44 pm-12:28 pm
2 stops15h 44m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$189
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/2
6:04 am-3:40 pm
1 stop7h 36m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$203
Quickest round-trip
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Wed 10/28
6:04 am-1:30 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$203
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Tue 10/27
6:44 pm-1:30 pm
2 stops17h 46m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$209
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/9
5:10 am-3:50 pm
1 stop8h 40m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$233
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Fri 11/13
6:00 am-3:30 pm
1 stop7h 30m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$263
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sun 1/3
6:00 am-4:49 pm
1 stop8h 49m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$263
Showing 1-10 of 20 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 October.
| 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 |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Punta Cana flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago Midway Airport-Punta Cana flight deals on Cheapflights vs. Ovago >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 Ovago the most. Ovago 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
How often are flights from Chicago to Punta Cana delayed?
About 39% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 90 minutes.
What is the most punctual flight time for Chicago to 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?
Friday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Punta Cana flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 39% of flights being delayed.
Reviews of airlines servicing 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 October 20, 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.
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
7.9
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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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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 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$478 | Average$1,001 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$511 | Average$831 | FlexibilityNo cancel fee | On-time63% |