Punta Cana

$141+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
ene. 11 — ene. 181
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Cheap flight deals from Midway to Punta Cana

Cheapest flights from Midway to Punta Cana
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 diciembre 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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.
mié. 12/106:00 amMDW - PUJ
1 stop6h 25mDelta
mié. 12/173:50 pmPUJ - MDW
1 stop9h 57mDelta
Deal found 12/10$366
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/256:12 amMDW - PUJ
1 stop6h 57mFrontier
mar. 12/3011:37 amPUJ - MDW
1 stop12h 35mFrontier
Deal found 12/10$380
This Delta deal was found by Cheapflights users on 12/10. 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.
vie. 12/126:00 amMDW - PUJ
1 stop6h 25mDelta
jue. 12/186:11 pmPUJ - MDW
1 stop7h 36mDelta
Deal found 12/10$396
This Mytrip deal was found by Cheapflights users on 12/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/248:15 amMDW - PUJ
1 stop28h 54mFrontier
mié. 12/314:19 pmPUJ - MDW
1 stop27h 19mFrontier
Deal found 12/10$402
This Southwest deal was found by Cheapflights users on 12/10. 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.
sáb. 12/137:40 amMDW - PUJ
1 stop6h 25mSouthwest
sáb. 12/203:25 pmPUJ - MDW
Nonstop5h 00mSouthwest
Deal found 12/10$416
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.
mié. 12/248:15 amMDW - PUJ
1 stop24h 12mFrontier
dom. 12/283:21 pmPUJ - MDW
1 stop8h 51mFrontier
Deal found 12/11$418
This Southwest deal was found by Cheapflights users on 12/10. 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.
dom. 12/145:10 amMDW - PUJ
1 stop6h 35mSouthwest
dom. 12/214:00 pmPUJ - MDW
2 stops9h 50mSouthwest
Deal found 12/10$426
This Southwest deal was found by Cheapflights users on 12/10. 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.
mar. 12/166:40 amMDW - PUJ
1 stop6h 30mSouthwest
mar. 12/234:00 pmPUJ - MDW
2 stops9h 50mSouthwest
Deal found 12/10$436
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.
mié. 12/313:10 pmMDW - PUJ
1 stop20h 59mMultiple Airlines
mié. 1/76:08 pmPUJ - MDW
2 stops47h 25mMultiple Airlines
Deal found 12/11$450
This Delta deal was found by Cheapflights users on 12/10. 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.
mié. 12/176:00 amMDW - PUJ
1 stop7h 39mDelta
mié. 12/243:38 pmPUJ - MDW
1 stop8h 44mDelta
Deal found 12/10$452
This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/268:15 amMDW - PUJ
1 stop24h 12mFrontier
mié. 12/314:19 pmPUJ - MDW
1 stop27h 19mFrontier
Deal found 12/10$454

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 diciembre 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$324
(Kiwi.com)

One-way from

$141
(Trip.com)

Popular in

November

Cheapest in

October

Average price

$925

Good round-trip deal

$381 or less
Provider with most accurate pricing for Chicago Midway-Punta Cana flight deals.
Provider most trusted by Cheapflights users for Chicago Midway-Punta Cana flights.
From Chicago Midway to Punta Cana
One-way flight from Chicago Midway to Punta Cana
Highest demand for flights based on searches. 7% potential increase in price ($62 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Average for round-trip flights in December 2025
Price to beat on a round-trip flight from Chicago Midway to Punta Cana.

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

Fly from

Midway

Fly to

Punta Cana

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dom. 1/18

6:45 am-4:41 pm

1 stop7h 56m

Punta Cana

jue. 1/22

4:55 pm-10:22 pm

1 stop7h 27m

$366

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 3/3

6:00 am-3:30 pm

1 stop7h 30m

Punta Cana

mar. 3/10

3:52 pm-10:29 pm

1 stop7h 37m

$366

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 1/12

6:45 am-4:41 pm

1 stop7h 56m

Punta Cana

sáb. 1/17

4:50 pm-10:07 pm

1 stop7h 17m

$382

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 3/3

5:00 am-2:30 pm

1 stop7h 30m

Punta Cana

mar. 3/10

2:35 pm-6:40 pm

Nonstop5h 05m

$402

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb. 1/31

6:25 am-3:25 pm

1 stop7h 00m

Punta Cana

sáb. 2/7

2:08 pm-10:22 pm

1 stop10h 14m

$426

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

vie. 1/23

6:00 am-2:20 pm

1 stop6h 20m

Punta Cana

lun. 1/26

4:55 pm-10:22 pm

1 stop7h 27m

$426

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 1/27

5:00 am-2:30 pm

1 stop7h 30m

Punta Cana

mar. 2/3

2:40 pm-10:05 pm

2 stops9h 25m

$433

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

vie. 2/6

5:30 am-2:30 pm

1 stop7h 00m

Punta Cana

mar. 2/10

2:40 pm-10:05 pm

2 stops9h 25m

$452

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 4/27

8:35 pm-2:15 pm

2 stops16h 40m

Punta Cana

lun. 5/4

2:05 pm-11:40 pm

1 stop10h 35m

$492

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

jue. 4/30

8:35 pm-3:00 pm

2 stops17h 25m

Punta Cana

jue. 5/7

2:05 pm-11:40 pm

1 stop10h 35m

$494

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 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 Chicago Midway Airport-Punta Cana flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago Midway Airport-Punta Cana flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.
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

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

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $266). Flying from Chicago Midway Airport to Punta Cana in August is currently the most expensive (average of $762). 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 diciembre 12, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 58% on flights from Chicago Midway Airport to Punta Cana by exploring options for tickets in the evening.

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 diciembre 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier 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.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Punta Cana. 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 into for flights to Punta Cana from Chicago Midway?

    If you book a flight to Punta Cana from Chicago Midway, you will be flying to Punta Cana, which is the city’s only airport. Punta Cana (PUJ) is located 9.2 mi from the center of Punta Cana. There are 0 flights from Chicago Midway to Punta Cana per day from 3 different airlines.

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

    There are many flights that can get you from Chicago Midway Airport to Punta Cana in 7h 30m. Fly via Delta or Southwest to get the fastest option. There are 1967 mi between Chicago Midway Airport and Punta Cana. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago Midway Airport to Punta Cana round-trip?

    Our cheapest airline available from Chicago Midway Airport to Punta Cana is Frontier. Our recent data shows that you can find tickets from as low as $370 on this airline. Additional options worth looking into are Southwest and Delta, starting at $495 and $539 round-trip. Users have found that Frontier is 50% cheaper than the other options available to this destination.

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

    Looking for the cheapest flight from Chicago Midway Airport to Punta Cana? While on average our users pay $503, our data indicates the cheapest price to be $348. The most popular route (Chicago Midway - Punta Cana), is priced around $338.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Punta Cana 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 Chicago Midway Airport to Punta Cana?

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $266). Flying from Chicago Midway Airport to Punta Cana in August is currently the most expensive (average of $762). 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 Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Bavaro

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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$495Average$740FlexibilityNo cancel feeOn-time63%
DeltaCheapest$539Average$869FlexibilityNo cancel feeOn-timeN/A

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