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Punta Cana

$133+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap 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 October 27, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$315
(Kiwi.com)

One-way from

$133
(Kiwi.com)

Popular in

November

Cheapest in

October

Average price

$482

Good round-trip deal

$919 or less
Provider with most accurate pricing for Chicago Midway-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Punta Cana flights.
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From Chicago Midway to Punta Cana
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One-way flight from Chicago Midway to Punta Cana
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Highest demand for flights based on searches. 8% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago Midway to Punta Cana.
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Find 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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/62:59 pmMDW - PUJ
1 stop25h 39mMultiple Airlines
Sat 12/139:38 amPUJ - MDW
1 stop14h 52mMultiple Airlines
Deal found 10/25$315
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 12/318:15 amMDW - PUJ
1 stop24h 12mMultiple Airlines
Wed 1/141:01 pmPUJ - MDW
1 stop27h 46mMultiple Airlines
Deal found 10/24$316
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.
Wed 12/318:15 amMDW - PUJ
1 stop28h 54mMultiple Airlines
Wed 1/76:08 pmPUJ - MDW
2 stops31h 17mMultiple Airlines
Deal found 10/26$320
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 12/42:16 pmMDW - PUJ
1 stop27h 38mMultiple Airlines
Thu 12/119:38 amPUJ - MDW
1 stop14h 15mMultiple Airlines
Deal found 10/26$331
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amMDW - PUJ
1 stop8h 46mDelta
Wed 12/105:04 pmPUJ - MDW
1 stop8h 43mDelta
Deal found 10/27$338
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 11/275:30 pmMDW - PUJ
1 stop24h 55mMultiple Airlines
Thu 12/43:08 pmPUJ - MDW
1 stop8h 50mMultiple Airlines
Deal found 10/26$339
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/152:05 pmMDW - PUJ
2 stops20h 03mMultiple Airlines
Sat 11/229:38 amPUJ - MDW
1 stop9h 19mMultiple Airlines
Deal found 10/24$349
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.
Mon 11/176:00 amMDW - PUJ
1 stop7h 38mDelta
Thu 11/203:50 pmPUJ - MDW
1 stop9h 50mDelta
Deal found 10/26$351

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 October 27, 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

Sun 12/7

6:00 am-4:46 pm

1 stop8h 46m

Punta Cana

Thu 12/11

6:11 pm-11:47 pm

1 stop7h 36m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/25

7:16 pm-4:09 pm

1 stop18h 53m

Punta Cana

Thu 2/12

6:05 pm-9:56 am

1 stop17h 51m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/12

7:16 pm-2:52 pm

1 stop17h 36m

Punta Cana

Thu 1/29

4:20 pm-9:08 am

1 stop18h 48m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/18

7:16 pm-4:09 pm

1 stop18h 53m

Punta Cana

Thu 2/5

3:45 pm-10:26 pm

1 stop8h 41m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/19

6:00 am-3:30 pm

1 stop7h 30m

Punta Cana

Thu 2/5

3:45 pm-10:26 pm

1 stop8h 41m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/18

7:16 pm-4:09 pm

1 stop18h 53m

Punta Cana

Mon 2/2

4:20 pm-9:08 am

1 stop18h 48m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/17

6:45 am-4:41 pm

1 stop7h 56m

Punta Cana

Wed 1/28

3:45 pm-10:26 pm

1 stop8h 41m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/20

6:00 am-2:20 pm

1 stop6h 20m

Punta Cana

Mon 2/2

4:20 pm-9:08 am

1 stop18h 48m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/19

6:00 am-3:30 pm

1 stop7h 30m

Punta Cana

Mon 2/2

4:20 pm-9:08 am

1 stop18h 48m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/31

5:00 pm-1:30 pm

2 stops18h 30m

Punta Cana

Thu 2/5

4:20 pm-9:08 am

1 stop18h 48m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 22 results
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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 October.
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

*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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $194). 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 October 27, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 59% 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 October 27, 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.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,996 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 8h 46m. Fly via Delta to get the fastest option. There are 1967 mi between Chicago Midway Airport and Punta Cana.

  • 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 49% 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 $919, our data indicates the cheapest price to be $617. The most popular route (Chicago Midway - Punta Cana), is priced around $317.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $194). 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 October 27, 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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