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$149+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Delta deal was found by Cheapflights users on 1/21. 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 5/52:40 pm
PUJ
-
MDW
1 stop8h 49m
Delta
Tue 5/126:00 am
MDW
-
PUJ
1 stop7h 48m
Delta
Deal found 1/21$369
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 2/185:47 pm
PUJ
-
MDW
2 stops30h 50m
Multiple Airlines
Sun 3/16:15 am
MDW
-
PUJ
1 stop10h 23m
Multiple Airlines
Deal found 1/18$390
This Booking.com deal was found by Cheapflights users on 1/19. 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.
Thu 3/54:14 pm
PUJ
-
MDW
2 stops32h 05m
Frontier
Thu 3/126:00 am
MDW
-
PUJ
1 stop7h 17m
Frontier
Deal found 1/19$458
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/37:10 pm
PUJ
-
MDW
2 stops25h 57m
Multiple Airlines
Sun 3/87:30 am
MDW
-
PUJ
1 stop7h 56m
Multiple Airlines
Deal found 1/19$479
This Booking.com deal was found by Cheapflights users on 1/20. 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.
Thu 3/124:11 pm
PUJ
-
MDW
2 stops21h 57m
Frontier
Wed 3/186:00 am
MDW
-
PUJ
1 stop7h 17m
Frontier
Deal found 1/20$502
This Southwest deal was found by Cheapflights users on 1/18. 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 5/912:55 pm
PUJ
-
MDW
Nonstop5h 00m
Southwest
Sat 5/169:40 am
MDW
-
PUJ
Nonstop4h 20m
Southwest
Deal found 1/18$541
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/273:32 pm
PUJ
-
MDW
1 stop7h 47m
Multiple Airlines
Sun 4/51:10 pm
MDW
-
PUJ
2 stops24h 25m
Multiple Airlines
Deal found 1/20$557
This Delta deal was found by Cheapflights users on 1/19. 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 2/243:50 pm
PUJ
-
MDW
1 stop8h 43m
Delta
Tue 3/36:00 am
MDW
-
PUJ
1 stop7h 30m
Delta
Deal found 1/19$618

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$369
(Delta)

One-way from

$149
(Southwest)

Popular in

June

Cheapest in

February

Average price

$459

Good one-way deal

$464 or less
Provider with most accurate pricing for Punta Cana-Chicago Midway flight deals.
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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 ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
Search Deals
Price to beat on a one-way flight from Punta Cana to Chicago Midway.
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 January 21, 2026.
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 5/5

2:40 pm-10:29 pm

1 stop8h 49m

Chicago Midway

Tue 5/12

6:00 am-2:48 pm

1 stop7h 48m

$369

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 2/18

5:47 pm-10:37 pm

2 stops30h 50m

Chicago Midway

Sun 3/1

6:15 am-6:38 pm

1 stop10h 23m

$390

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 3/12

4:11 pm-1:08 pm

2 stops21h 57m

Chicago Midway

Wed 3/18

6:00 am-2:17 pm

1 stop7h 17m

$502

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 5/9

12:55 pm-4:55 pm

Nonstop5h 00m

Chicago Midway

Sat 5/16

9:40 am-3:00 pm

Nonstop4h 20m

$541

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 3/27

3:32 pm-10:19 pm

1 stop7h 47m

Chicago Midway

Sun 4/5

6:00 am-2:15 pm

1 stop7h 15m

$545

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 3/27

3:32 pm-10:19 pm

1 stop7h 47m

Chicago Midway

Sun 4/5

1:10 pm-2:35 pm

2 stops24h 25m

$557

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 2/24

3:50 pm-10:33 pm

1 stop8h 43m

Chicago Midway

Tue 3/3

6:00 am-3:30 pm

1 stop7h 30m

$618

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 5/5

2:05 pm-7:35 am

2 stops18h 30m

Chicago Midway

Tue 5/12

6:00 am-1:05 pm

1 stop6h 05m

$628

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 5/9

2:40 pm-9:45 pm

1 stop8h 05m

Chicago Midway

Sat 5/16

6:00 am-1:24 pm

1 stop6h 24m

$629

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 3/5

4:55 pm-10:31 pm

1 stop7h 36m

Chicago Midway

Thu 3/12

6:00 am-1:20 pm

1 stop6h 20m

$643

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 21 results
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2
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  • Most accurate provider: When it comes to deals on Punta Cana-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Punta Cana-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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.

Cheapflights Insights

Everything you need to know about your flight from Punta Cana to Chicago Midway Airport

What is the cheapest time of day to fly from PUJ to MDW?

Find hourly flight availability from Punta Cana to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2026.

When flying from Punta Cana to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 5h. 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 $563, our data indicates the cheapest price to be $266. The most popular route (Punta Cana - Chicago Midway), is priced around $447.

  • 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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