HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$148+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Punta Cana to Midway 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.

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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/246:08 pmPUJ - MDW
2 stops25h 30mMultiple Airlines
Wed 12/316:12 amMDW - PUJ
1 stop26h 15mMultiple Airlines
Deal found 10/28$306
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/49:38 amPUJ - MDW
1 stop14h 15mMultiple Airlines
Thu 12/112:16 pmMDW - PUJ
1 stop27h 38mMultiple Airlines
Deal found 10/26$317
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/233:39 pmPUJ - MDW
2 stops24h 58mMultiple Airlines
Mon 1/199:43 pmMDW - PUJ
1 stop18h 17mMultiple Airlines
Deal found 10/27$319
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/69:38 amPUJ - MDW
1 stop14h 52mMultiple Airlines
Sat 12/132:59 pmMDW - PUJ
1 stop25h 39mMultiple Airlines
Deal found 10/26$331
This Delta deal was found by Cheapflights users on 10/26. 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 12/25:04 pmPUJ - MDW
1 stop8h 43mDelta
Tue 12/96:00 amMDW - PUJ
1 stop6h 25mDelta
Deal found 10/26$344
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/86:08 pmPUJ - MDW
2 stops40h 38mMultiple Airlines
Mon 12/153:10 pmMDW - PUJ
1 stop24h 50mMultiple Airlines
Deal found 10/28$353
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/83:11 pmPUJ - MDW
2 stops22h 19mMultiple Airlines
Sat 11/1511:36 amMDW - PUJ
1 stop29h 14mMultiple Airlines
Deal found 10/26$358
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/2310:40 amPUJ - MDW
1 stop29h 57mMultiple Airlines
Tue 12/306:14 amMDW - PUJ
2 stops32h 36mMultiple Airlines
Deal found 10/26$367

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$306
(Kiwi.com)

One-way from

$148
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$511
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.
Search Deals
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. 12% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 28, 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

Tue 12/2

5:04 pm-11:47 pm

1 stop8h 43m

Chicago Midway

Tue 12/9

6:00 am-3:39 pm

1 stop7h 39m

$344

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

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/17

2:08 pm-10:09 pm

1 stop10h 01m

Chicago Midway

Sat 1/24

6:00 am-4:41 pm

1 stop8h 41m

$379

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/31

3:00 pm-5:55 pm

Nonstop4h 55m

Chicago Midway

Sat 2/7

8:15 am-2:35 pm

Nonstop4h 20m

$384

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 11/22

3:20 pm-6:20 pm

Nonstop5h 00m

Chicago Midway

Sat 11/29

5:25 am-3:30 pm

1 stop8h 05m

$384

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/17

3:35 pm-10:10 pm

1 stop8h 35m

Chicago Midway

Sat 1/24

8:15 am-2:35 pm

Nonstop4h 20m

$394

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 1/24

3:35 pm-10:10 pm

1 stop8h 35m

Chicago Midway

Sat 1/31

8:15 am-2:35 pm

Nonstop4h 20m

$394

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 12/3

2:40 pm-9:05 pm

1 stop8h 25m

Chicago Midway

Wed 12/10

5:05 am-3:00 pm

1 stop7h 55m

$394

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 12/15

2:38 pm-11:47 pm

1 stop11h 09m

$189

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/23

6:06 pm-10:01 am

1 stop17h 55m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 18 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 October.
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 4h 55m. 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.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Punta Cana to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.