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Punta Cana

$139+ 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
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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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 January 26, 2026.

This Travelocity deal was found by Cheapflights users on 1/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
-
PUJ
1 stop6h 46m
Frontier
Sat 5/22:56 pm
PUJ
-
MDW
1 stop8h 23m
Frontier
Deal found 1/24$329
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
-
PUJ
1 stop6h 46m
Frontier
Sat 5/92:56 pm
PUJ
-
MDW
1 stop8h 23m
Frontier
Deal found 1/25$357
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Fri 2/66:20 am
MDW
-
PUJ
1 stop30h 41m
Multiple Airlines
Thu 2/125:47 pm
PUJ
-
MDW
2 stops26h 06m
Multiple Airlines
Deal found 1/24$360
This Trip.com deal was found by Cheapflights users on 1/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
-
PUJ
1 stop7h 17m
Frontier
Sat 3/72:16 pm
PUJ
-
MDW
1 stop9h 29m
Frontier
Deal found 1/24$367
This Frontier deal was found by Cheapflights users on 1/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:04 pm
MDW
-
PUJ
2 stops14h 05m
Frontier
Sat 4/182:56 pm
PUJ
-
MDW
1 stop8h 23m
Frontier
Deal found 1/24$376
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Thu 3/56:15 am
MDW
-
PUJ
1 stop8h 16m
Multiple Airlines
Thu 3/129:38 am
PUJ
-
MDW
2 stops13h 41m
Multiple Airlines
Deal found 1/24$381
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 2/85:13 pm
MDW
-
PUJ
2 stops21h 23m
Multiple Airlines
Wed 2/111:01 pm
PUJ
-
MDW
1 stop26h 55m
Multiple Airlines
Deal found 1/25$387
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
-
PUJ
2 stops12h 17m
Frontier
Sat 3/72:16 pm
PUJ
-
MDW
1 stop9h 29m
Frontier
Deal found 1/25$388
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 2/226:15 am
MDW
-
PUJ
1 stop10h 23m
Multiple Airlines
Sun 3/112:12 pm
PUJ
-
MDW
2 stops36h 17m
Multiple Airlines
Deal found 1/25$389
This CheapOair deal was found by Cheapflights users on 1/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
-
PUJ
1 stop27h 07m
Frontier
Wed 4/151:16 pm
PUJ
-
MDW
2 stops19h 48m
Frontier
Deal found 1/24$394

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Travelocity)

One-way from

$139
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$714

Good round-trip deal

$579 or less
Provider with most accurate pricing for Chicago Midway-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Punta Cana flights.
Search Deals
From Chicago Midway to Punta Cana
Search Deals
One-way flight from Chicago Midway to Punta Cana
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($171 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Punta Cana.
Search Deals

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 January 26, 2026.
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 4/26

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Wed 4/29

2:46 pm-10:28 pm

1 stop8h 42m

$397

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 4/12

6:00 am-2:25 pm

1 stop7h 25m

Punta Cana

Thu 4/16

3:57 pm-10:28 pm

1 stop7h 31m

$397

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/23

6:07 pm-12:40 pm

2 stops17h 33m

Punta Cana

Tue 3/31

3:50 pm-5:54 pm

2 stops27h 04m

$401

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 4/11

9:40 am-3:00 pm

Nonstop4h 20m

Punta Cana

Thu 4/16

2:05 pm-11:40 pm

1 stop10h 35m

$417

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 4/9

7:10 am-3:00 pm

1 stop6h 50m

Punta Cana

Tue 4/14

2:05 pm-9:25 pm

1 stop8h 20m

$462

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 3/3

5:00 am-2:30 pm

1 stop7h 30m

Punta Cana

Sat 3/14

2:50 pm-7:00 pm

Nonstop5h 10m

$488

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 3/18

9:15 am-2:30 pm

Nonstop4h 15m

Punta Cana

Wed 3/25

2:35 pm-6:40 pm

Nonstop5h 05m

$494

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/9

9:15 am-2:30 pm

Nonstop4h 15m

Punta Cana

Sun 3/15

2:35 pm-12:50 am

1 stop11h 15m

$513

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/14

8:25 am-2:50 pm

Nonstop4h 25m

Punta Cana

Thu 2/19

2:40 pm-10:25 pm

1 stop9h 45m

$520

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 2/26

9:20 pm-2:30 pm

2 stops15h 10m

Punta Cana

Wed 3/4

2:40 pm-9:00 pm

1 stop8h 20m

$522

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Punta Cana flight deals on Cheapflights vs. FlightHub >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 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 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 $252). Flying from Chicago Midway Airport to Punta Cana in December is currently the most expensive (average of $863). 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 January 26, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Punta Cana as you normally would.

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 January 26, 2026.
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
4,268 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

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
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

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
Delta
7.9
Good
8,113 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

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
Frontier
5.7
Fair
3,058 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

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 4h 20m. 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 $418 and $539 round-trip. Users have found that Frontier is 52% 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 $759, our data indicates the cheapest price to be $475. The most popular route (Chicago Midway - Punta Cana), is priced around $357.

  • 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 $252). Flying from Chicago Midway Airport to Punta Cana in December is currently the most expensive (average of $863). 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$418Average$660FlexibilityNo cancel feeOn-time63%
DeltaCheapest$539Average$779FlexibilityNo cancel feeOn-timeN/A

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