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$178+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$384
(Southwest)

One-way from

$178
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$460

Good one-way deal

$549 or less
From Punta Cana to Chicago Midway
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One-way flight from Punta Cana to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($157 potential increase over avg. RT price).
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Cheapest flight prices on average. 13% potential price decrease ($75 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Punta Cana to Chicago Midway.
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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.
Fri 10/33:30 pmPUJ - MDW
1 stop7h 50mSouthwest
Mon 10/65:00 amMDW - PUJ
1 stop8h 30mSouthwest
Deal found 9/11$384
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/171:57 pmPUJ - MDW
2 stops20h 43mDelta
Mon 9/226:15 pmMDW - PUJ
2 stops17h 17mDelta
Deal found 9/10$445
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 9/173:59 pmPUJ - MDW
2 stops17h 41mDelta
Tue 9/236:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 9/9$462
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:10 pmPUJ - MDW
1 stop8h 55mSouthwest
Wed 12/35:05 amMDW - PUJ
1 stop7h 55mSouthwest
Deal found 9/10$466
This eDestinos deal was found by Cheapflights users on 9/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/99:38 amPUJ - MDW
1 stop26h 49mMultiple Airlines
Wed 10/158:05 amMDW - PUJ
2 stops24h 27mMultiple Airlines
Deal found 9/11$471
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.
Wed 9/173:05 pmPUJ - MDW
2 stops18h 00mSouthwest
Tue 9/236:25 amMDW - PUJ
1 stop6h 40mSouthwest
Deal found 9/9$485
This Mytrip deal was found by Cheapflights users on 9/11. 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.
Thu 10/231:32 pmPUJ - MDW
2 stops11h 14mFrontier
Sun 10/266:20 amMDW - PUJ
2 stops28h 49mFrontier
Deal found 9/11$533
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/173:05 pmPUJ - MDW
2 stops18h 00mSouthwest
Mon 9/225:10 amMDW - PUJ
1 stop7h 55mSouthwest
Deal found 9/10$558

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 September 11, 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 10/23

3:30 pm-10:20 pm

1 stop7h 50m

Chicago Midway

Sun 10/26

6:25 am-2:20 pm

1 stop6h 55m

$384

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 10/3

3:30 pm-10:20 pm

1 stop7h 50m

Chicago Midway

Mon 10/6

5:00 am-2:30 pm

1 stop8h 30m

$384

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$396

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 2/14

4:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Sat 2/21

6:00 am-2:56 pm

1 stop6h 56m

$433

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 11/26

4:10 pm-11:05 pm

1 stop8h 55m

Chicago Midway

Wed 12/3

5:05 am-3:00 pm

1 stop7h 55m

$466

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/23

1:32 pm-11:46 pm

2 stops11h 14m

Chicago Midway

Sun 10/26

6:20 am-12:09 pm

2 stops28h 49m

$533

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 2/14

9:38 am-11:25 pm

2 stops15h 47m

Chicago Midway

Fri 2/20

8:56 pm-12:54 pm

1 stop13h 58m

$535

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/23

9:38 am-11:17 am

1 stop26h 39m

$178

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 10/27

12:10 pm-11:03 pm

1 stop11h 53m

$187

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 11/7

1:10 pm-10:26 am

1 stop23h 16m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 results
1
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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 50m. Punta Cana and Chicago Midway Airport are separated by a distance of 1967 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Punta Cana to Chicago Midway Airport?

    Looking for the cheapest flight from Punta Cana to Chicago Midway Airport? While on average our users pay $549, our data indicates the cheapest price to be $525. The most popular route (Punta Cana - Chicago Midway), is priced around $396.

  • 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.

  • What is the cheapest month to book a flight from Punta Cana to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Punta Cana to Chicago Midway Airport (average of $160). Flying from Punta Cana to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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