$152+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Apr 11 — Apr 181
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 March 12, 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 March 12, 2026.
This FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:14 am
MDW
- PUJ
2 stops25h 55m
Frontier
Sat 5/92:56 pm
PUJ
- MDW
1 stop8h 23m
Frontier
Deal found 3/8![Frontier logo]()
$332
This Priceline deal was found by Cheapflights users on 3/9. 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.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Sat 4/1811:07 am
PUJ
- MDW
1 stop21h 52m
Frontier
Deal found 3/9![Frontier logo]()
$339
This FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MDW
- PUJ
1 stop6h 46m
Frontier
Sat 5/162:56 pm
PUJ
- MDW
1 stop8h 23m
Frontier
Deal found 3/8![Frontier logo]()
$349
This Frontier deal was found by Cheapflights users on 3/8. 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.
Sat 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Fri 4/241:37 pm
PUJ
- MDW
2 stops9h 49m
Frontier
Deal found 3/8![Frontier logo]()
$360
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:40 am
MDW
- PUJ
1 stop26h 27m
Frontier
Sat 4/1811:07 am
PUJ
- MDW
1 stop21h 52m
Frontier
Deal found 3/9![Frontier logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/217:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Thu 4/239:38 am
PUJ
- MDW
2 stops13h 44m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Tue 5/199:38 am
PUJ
- MDW
2 stops34h 53m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/147:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Tue 4/217:10 pm
PUJ
- MDW
1 stop18h 50m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$372
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 March 12, 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 March 12, 2026.
This Delta deal was found by Cheapflights users on 3/9. 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.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 21m
Delta
Fri 4/172:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 3/9![Delta logo]()
$521
This Southwest deal was found by Cheapflights users on 3/8. 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.
Fri 5/18:35 pm
MDW
- PUJ
2 stops16h 40m
Southwest
Mon 5/42:05 pm
PUJ
- MDW
1 stop11h 00m
Southwest
Deal found 3/8![Southwest logo]()
$555
This Southwest deal was found by Cheapflights users on 3/9. 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 5/159:25 pm
MDW
- PUJ
1 stop13h 30m
Southwest
Mon 5/184:00 pm
PUJ
- MDW
2 stops18h 10m
Southwest
Deal found 3/9![Southwest logo]()
$578
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 6/95:59 pm
MDW
- PUJ
2 stops17h 21m
Delta
Fri 6/124:15 pm
PUJ
- MDW
2 stops21h 15m
Delta
Deal found 3/8![Delta logo]()
$603
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:40 am
MDW
- PUJ
Nonstop4h 20m
Southwest
Thu 5/71:40 pm
PUJ
- MDW
1 stop9h 40m
Southwest
Deal found 3/12![Southwest logo]()
$593
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 4/266:00 am
MDW
- PUJ
1 stop7h 32m
Delta
Tue 5/53:57 pm
PUJ
- MDW
1 stop7h 31m
Delta
Deal found 3/8![Delta logo]()
$609
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:40 am
MDW
- PUJ
Nonstop4h 20m
Southwest
Wed 4/152:05 pm
PUJ
- MDW
1 stop8h 20m
Southwest
Deal found 3/11![Southwest logo]()
$624
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 6/95:59 pm
MDW
- PUJ
2 stops17h 21m
Delta
Sat 6/135:15 pm
PUJ
- MDW
1 stop17h 36m
Delta
Deal found 3/8![Delta logo]()
$688
This Southwest deal was found by Cheapflights users on 3/8. 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.
Mon 6/19:25 pm
MDW
- PUJ
2 stops14h 40m
Southwest
Mon 6/81:25 pm
PUJ
- MDW
2 stops10h 35m
Southwest
Deal found 3/8![Southwest logo]()
$718
This Delta deal was found by Cheapflights users on 3/7. 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.
Mon 5/46:00 am
MDW
- PUJ
1 stop6h 21m
Delta
Thu 5/72:50 pm
PUJ
- MDW
1 stop7h 19m
Delta
Deal found 3/7![Delta logo]()
$735
This Delta deal was found by Cheapflights users on 3/11. 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.
Mon 5/46:00 am
MDW
- PUJ
1 stop6h 21m
Delta
Sat 5/92:50 pm
PUJ
- MDW
1 stop7h 19m
Delta
Deal found 3/11![Delta logo]()
$754
Last-minute flights from Midway to Punta CanaDiscover last-minute flight deals from Midway to Punta Cana. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Punta Cana. Data last updated March 12, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:40 am
MDW
- PUJ
1 stop26h 27m
Frontier
Sat 4/1811:07 am
PUJ
- MDW
1 stop21h 52m
Frontier
Deal found 3/9![Frontier logo]()
$364
This Orbitz deal was found by Cheapflights users on 3/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- PUJ
1 stop6h 45m
Frontier
Sat 4/1811:07 am
PUJ
- MDW
1 stop21h 52m
Frontier
Deal found 3/9![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/147:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Tue 4/217:10 pm
PUJ
- MDW
1 stop18h 50m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$372
This Frontier deal was found by Cheapflights users on 3/8. 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.
Sat 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Fri 4/241:37 pm
PUJ
- MDW
2 stops9h 49m
Frontier
Deal found 3/8![Frontier logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/217:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Thu 4/239:38 am
PUJ
- MDW
2 stops13h 44m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/217:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Tue 4/287:10 pm
PUJ
- MDW
1 stop18h 50m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$381
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Wed 4/299:13 pm
PUJ
- MDW
2 stops26h 06m
Frontier
Deal found 3/9![Frontier logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Sat 5/29:38 am
PUJ
- MDW
2 stops13h 36m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$375
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 March 12, 2026.
Search for one-way flight options from Midway to Punta Cana. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:30 am
MDW
- PUJ
1 stop9h 01m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$152
This Super.com deal was found by Cheapflights users on 3/9. 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 4/186:00 am
MDW
- PUJ
1 stop6h 54m
Frontier
Deal found 3/9![Frontier logo]()
$155
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:30 am
MDW
- PUJ
1 stop12h 24m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- PUJ
1 stop12h 45m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$160
This Trip.com deal was found by Cheapflights users on 3/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:30 am
MDW
- PUJ
1 stop13h 59m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$161
This Priceline deal was found by Cheapflights users on 3/9. 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.
Sat 5/309:16 pm
MDW
- PUJ
1 stop15h 59m
Frontier
Deal found 3/9![Frontier logo]()
$163
This Super.com deal was found by Cheapflights users on 3/9. 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.
Fri 5/89:14 am
MDW
- PUJ
1 stop23h 43m
Frontier
Deal found 3/9![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/209:14 am
MDW
- PUJ
1 stop30h 26m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/127:30 am
MDW
- PUJ
1 stop7h 49m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$168
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 March 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (FlightHub) |
One-way from | $152 (Trip.com) |
Popular in | March |
Cheapest in | October |
Average price | $1,125 |
Good round-trip deal | $571 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 March 12, 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 4/13
6:00 am-1:21 pm
1 stop6h 21m
Punta Cana
Fri 4/17
2:46 pm-10:28 pm
1 stop8h 42m
$521
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 5/1
8:35 pm-2:15 pm
2 stops16h 40m
Punta Cana
Mon 5/4
2:05 pm-12:05 am
1 stop11h 00m
$555
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 5/15
9:25 pm-11:55 am
1 stop13h 30m
Punta Cana
Mon 5/18
4:00 pm-9:10 am
2 stops18h 10m
$578
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 5/2
9:40 am-3:00 pm
Nonstop4h 20m
Punta Cana
Thu 5/7
1:40 pm-10:20 pm
1 stop9h 40m
$593
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/9
5:59 pm-12:20 pm
2 stops17h 21m
Punta Cana
Fri 6/12
4:15 pm-12:30 pm
2 stops21h 15m
$603
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/26
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
Tue 5/5
3:57 pm-10:28 pm
1 stop7h 31m
$609
Quickest round-trip
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 4/11
9:40 am-3:00 pm
Nonstop4h 20m
Punta Cana
Wed 4/15
2:05 pm-9:25 pm
1 stop8h 20m
$624
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/9
5:59 pm-12:20 pm
2 stops17h 21m
Punta Cana
Sat 6/13
5:15 pm-9:51 am
1 stop17h 36m
$688
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 6/1
9:25 pm-1:05 pm
2 stops14h 40m
Punta Cana
Mon 6/8
1:25 pm-11:00 pm
2 stops10h 35m
$718
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 5/4
6:00 am-1:21 pm
1 stop6h 21m
Punta Cana
Thu 5/7
2:50 pm-9:09 pm
1 stop7h 19m
$735
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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 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
More
What is the cheapest month to book a flight from Chicago Midway Airport to Punta Cana?
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $252). Flying from Chicago Midway Airport to Punta Cana in December is currently the most expensive (average of $863). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to 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 March 12, 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 24% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 109 minutes.
What is the most punctual flight time for Chicago to 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 Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Punta Cana flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.
What’s the top layover airport for flights from Chicago Midway Airport to Punta Cana?
Share of 1-stop round-trip flights from Chicago Midway Airport to Punta Cana chosen by Cheapflights users in the past 12 months, using the same layover each way.
Baltimore (BWI) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago Midway Airport to Punta Cana on Cheapflights.
What’s the cheapest layover airport for flights from Chicago Midway Airport to Punta Cana?
Average round-trip fare for 1-stop flights from Chicago Midway Airport to Punta Cana, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $606.
What’s the fastest layover option from Chicago Midway Airport to Punta Cana?
Shortest average travel time for 1-stop one-way flights from Chicago Midway Airport to Punta Cana, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 8h 03m.
Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Punta Cana?
Average layover duration for 1-stop one-way flights from Chicago Midway Airport to Punta Cana, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.
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 March 12, 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.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
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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 March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$418 | Average$659 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$539 | Average$779 | FlexibilityNo cancel fee | On-timeN/A |