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$162+ Cheap flights from Punta Cana (PUJ) to Midway (MDW)

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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Punta Cana to Midway

Cheapest flights from Punta Cana to Midway
Explore the most affordable flight options available from Punta Cana to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Mytrip deal was found by Cheapflights users on 12/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:37 amPUJ - MDW
1 stop12h 35mFrontier
Thu 1/16:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/11$340
This Booking.com deal was found by Cheapflights users on 12/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:19 pmPUJ - MDW
1 stop27h 19mFrontier
Wed 12/316:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/9$345
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:19 pmPUJ - MDW
1 stop7h 53mMultiple Airlines
Wed 12/313:10 pmMDW - PUJ
1 stop20h 59mMultiple Airlines
Deal found 12/11$356
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:08 pmPUJ - MDW
1 stop8h 50mMultiple Airlines
Thu 1/16:12 amMDW - PUJ
2 stops32h 38mMultiple Airlines
Deal found 12/11$358
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:37 amPUJ - MDW
1 stop8h 01mMultiple Airlines
Wed 12/313:10 pmMDW - PUJ
1 stop20h 59mMultiple Airlines
Deal found 12/11$364
This Priceline deal was found by Cheapflights users on 12/11. 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 12/2511:37 amPUJ - MDW
1 stop12h 35mFrontier
Thu 1/16:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/11$372

Find flight deals from Punta Cana to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Punta Cana (PUJ) to Midway (MDW). 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$326
(Kiwi.com)

One-way from

$162
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$397
Provider with most accurate pricing for Punta Cana-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago Midway flights.
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From Punta Cana to Chicago Midway
Search Deals
One-way flight from Punta Cana to Chicago Midway
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Punta Cana to Midway 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 December 12, 2025.
Use the filters below to find and compare flights from Punta Cana to Chicago Midway Airport that are best for you.

Fly from

Punta Cana

Fly to

Midway

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 1/22

4:55 pm-10:22 pm

1 stop7h 27m

Chicago Midway

Tue 1/27

6:00 am-3:30 pm

1 stop7h 30m

$377

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 1/26

4:55 pm-10:22 pm

1 stop7h 27m

Chicago Midway

Mon 2/2

6:00 am-3:30 pm

1 stop7h 30m

$412

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 12/29

4:46 pm-10:22 pm

1 stop7h 36m

Chicago Midway

Mon 1/5

6:45 am-3:40 pm

1 stop6h 55m

$455

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/17

2:45 pm-10:29 pm

1 stop8h 44m

Chicago Midway

Tue 3/24

6:30 am-2:25 pm

1 stop6h 55m

$460

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 12/23

4:00 pm-11:50 pm

2 stops9h 50m

Chicago Midway

Tue 12/30

5:45 am-3:10 pm

1 stop7h 25m

$479

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/26

4:10 pm-10:45 pm

1 stop8h 35m

Chicago Midway

Thu 3/5

9:15 am-3:30 pm

Nonstop4h 15m

$488

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 1/28

2:40 pm-10:05 pm

2 stops9h 25m

Chicago Midway

Wed 2/4

5:00 am-2:30 pm

1 stop7h 30m

$495

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/22

1:10 pm-9:45 pm

1 stop9h 35m

Chicago Midway

Wed 4/29

6:00 am-2:48 pm

1 stop7h 48m

$495

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 12/27

3:25 pm-6:25 pm

Nonstop5h 00m

Chicago Midway

Sat 1/3

5:05 am-4:30 pm

1 stop9h 25m

$523

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/27

4:10 pm-10:45 pm

1 stop8h 35m

Chicago Midway

Fri 3/6

9:15 am-3:30 pm

Nonstop4h 15m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 20 results
1
2

Compare providers for flights from Punta Cana to Midway

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 Punta Cana to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Punta Cana-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Punta Cana-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Punta Cana-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Punta Cana-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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 Punta Cana-Chicago Midway Airport 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 Punta Cana to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Punta Cana with our price prediction graph.
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.

Related info for your journey

Find useful and relevant information for your journey from Punta Cana to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Punta Cana to Chicago Midway?

    Punta Cana (PUJ) is the airport you will fly out of if you book a flight from Punta Cana to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Punta Cana; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Punta Cana airport to Chicago Midway. It is only a 9.2 mi journey to Punta Cana (PUJ) from Punta Cana’s city center.

  • How long is the flight from Punta Cana to Chicago Midway Airport?

    Departing from Punta Cana to Chicago Midway Airport will take you 7h 27m. Punta Cana and Chicago Midway Airport are separated by a distance of 1967 mi.

  • Can I find deals for flights from Punta Cana to Midway that include hotel bookings?

    Yes. In addition to deals on Punta Cana to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Punta Cana to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Punta Cana to Midway.

  • Can I find deals for business class flights from Punta Cana to Midway?

    Yes. Cheapflights offers flight deals from Punta Cana to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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