$184+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Oct 9 — Oct 161
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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Best
Last-minute
One-way
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 September 9, 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 September 9, 2026.
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:13 pm -
1 stop17h 15m
Thu 11/124:55 pm -
1 stop7h 59m
Deal found 9/7![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 9/7. 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 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
Tue 11/33:55 pm -
1 stop8h 38m
Deal found 9/7![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:30 am -
2 stops24h 58m
Sat 11/143:45 pm -
1 stop19h 05m
Deal found 9/7![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 9/7. 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 10/265:00 am -
1 stop6h 25m
Fri 10/302:45 pm -
1 stop8h 15m
Deal found 9/7![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 9/7. 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 10/265:00 am -
1 stop6h 25m
Mon 11/24:50 pm -
2 stops18h 10m
Deal found 9/7![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:31 pm -
2 stops20h 57m
Wed 11/184:55 pm -
1 stop7h 59m
Deal found 9/7![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 9/4. 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 10/275:45 am -
1 stop7h 00m
Tue 11/32:40 pm -
2 stops10h 00m
Deal found 9/4![Southwest logo]()
$469
This Southwest deal was found by Cheapflights users on 9/7. 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.
Tue 11/175:20 am -
1 stop7h 20m
Tue 11/244:10 pm -
1 stop9h 00m
Deal found 9/7![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 9/7. 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 11/288:40 am -
Nonstop4h 35m
Sat 12/53:35 pm -
1 stop8h 05m
Deal found 9/7![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sun 11/157:00 am -
1 stop6h 50m
Sun 11/224:05 pm -
2 stops19h 15m
Deal found 9/7![Southwest logo]()
$485
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 September 9, 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 September 9, 2026.
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:13 pm -
1 stop17h 15m
Wed 11/184:55 pm -
1 stop7h 59m
Deal found 9/7![Delta logo]()
$460
This Southwest deal was found by Cheapflights users on 9/7. 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 10/285:45 am -
1 stop7h 00m
Wed 11/42:40 pm -
2 stops10h 00m
Deal found 9/7![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 9/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:13 pm -
1 stop17h 15m
Mon 11/161:53 pm -
2 stops24h 58m
Deal found 9/7![Delta logo]()
$593
This Southwest deal was found by Cheapflights users on 9/7. 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 11/238:25 pm -
2 stops17h 25m
Wed 11/254:10 pm -
1 stop9h 00m
Deal found 9/7![Southwest logo]()
$640
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:04 am -
1 stop6h 26m
Sat 10/314:05 pm -
1 stop7h 28m
Deal found 9/6![Delta logo]()
$595
This Delta deal was found by Cheapflights users on 9/4. 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 11/275:29 pm -
1 stop18h 51m
Fri 12/44:55 pm -
2 stops18h 42m
Deal found 9/4![Delta logo]()
$623
This Southwest deal was found by Cheapflights users on 9/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:20 am -
1 stop7h 20m
Tue 11/173:35 pm -
1 stop7h 50m
Deal found 9/8![Southwest logo]()
$696
This Southwest deal was found by Cheapflights users on 9/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 am -
1 stop7h 25m
Fri 9/251:45 pm -
1 stop10h 00m
Deal found 9/8![Southwest logo]()
$712
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:04 am -
1 stop6h 26m
Thu 10/224:05 pm -
1 stop7h 28m
Deal found 9/9![Delta logo]()
$650
This Delta deal was found by Cheapflights users on 9/7. 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 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 11/13:55 pm -
1 stop8h 38m
Deal found 9/7![Delta logo]()
$676
This Southwest deal was found by Cheapflights users on 9/4. 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 10/195:00 am -
1 stop6h 25m
Mon 10/262:45 pm -
1 stop8h 15m
Deal found 9/4![Southwest logo]()
$773
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 10/306:04 am -
1 stop6h 26m
Sat 11/75:05 pm -
1 stop7h 28m
Deal found 9/8![Delta logo]()
$721
Last-minute flights from Midway to Punta CanaDiscover last-minute flight deals from Midway to Punta Cana. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Punta Cana. Data last updated September 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:20 pm -
2 stops15h 25m
Wed 10/72:45 pm -
1 stop7h 40m
Deal found 9/8![Southwest logo]()
$491
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sun 10/255:10 am -
1 stop7h 40m
Thu 10/292:45 pm -
1 stop8h 15m
Deal found 9/9![Southwest logo]()
$475
This Southwest deal was found by Cheapflights users on 9/7. 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 10/265:00 am -
1 stop6h 25m
Fri 10/302:45 pm -
1 stop8h 15m
Deal found 9/7![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 9/7. 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 10/265:00 am -
1 stop6h 25m
Mon 11/24:50 pm -
2 stops18h 10m
Deal found 9/7![Southwest logo]()
$455
This Delta deal was found by Cheapflights users on 9/7. 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 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
Tue 11/33:55 pm -
1 stop8h 38m
Deal found 9/7![Delta logo]()
$410
This Southwest deal was found by Cheapflights users on 9/4. 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 10/275:45 am -
1 stop7h 00m
Tue 11/32:40 pm -
2 stops10h 00m
Deal found 9/4![Southwest logo]()
$469
This Southwest deal was found by Cheapflights users on 9/5. 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 10/285:45 am -
1 stop7h 00m
Wed 11/43:35 pm -
1 stop7h 50m
Deal found 9/5![Southwest logo]()
$486
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 September 9, 2026.
Search for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Southwest deal was found by Cheapflights users on 9/7. 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 11/288:40 am -
Nonstop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 9/7. 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.
Tue 10/275:45 am -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$188
This Delta deal was found by Cheapflights users on 9/6. 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 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 9/6![Delta logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:07 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:04 pm -
2 stops17h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
2 stops33h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:24 am -
2 stops29h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
2 stops33h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
2 stops28h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 12/79:23 pm -
2 stops33h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:07 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$223
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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $401 (Delta) |
One-way from | $184 (Southwest) |
Popular in | June |
Cheapest in | November |
Average price | $731 |
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 September 9, 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
Fri 11/13
5:13 pm-12:28 pm
1 stop17h 15m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$238
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 11/2
6:04 am-2:30 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$238
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 9/12
5:00 am-1:25 pm
1 stop7h 25m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$258
Quickest round-trip
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Sat 9/12
6:05 am-1:25 pm
1 stop6h 20m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$258
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Thu 11/12
8:40 pm-3:10 pm
2 stops16h 30m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$264
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 9/21
6:25 am-12:48 pm
2 stops29h 23m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$315
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Fri 10/30
6:04 am-1:30 pm
1 stop6h 26m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$323
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 9/21
6:05 am-1:25 pm
1 stop6h 20m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$323
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Mon 12/7
6:00 am-3:29 pm
1 stop7h 29m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$323
ChicagoPunta Cana
MDW Chicago Midway - PUJ Punta Cana
MDWPUJ
Chicago Midway
Tue 11/10
5:13 pm-12:28 pm
1 stop17h 15m
Punta Cana
Wed 11/18
4:55 pm-10:54 pm
1 stop7h 59m
$460
Showing 1-10 of 21 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 September.
| 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 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
How often are flights from Chicago to Punta Cana delayed?
About 40% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 91 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 40% 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 September 9, 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.
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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Top 2 airlines flying from Midway to Punta Cana
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$478 | Average$960 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$503 | Average$860 | FlexibilityNo cancel fee | On-time63% |