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Punta Cana

$173+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
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 July 24, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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.
Mon 8/315:00 am
MDW
-
PUJ
1 stop7h 40m
Southwest
Thu 9/31:45 pm
PUJ
-
MDW
1 stop8h 45m
Southwest
Deal found 7/23$380
This Delta deal was found by Cheapflights users on 7/23. 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.
Sat 9/264:30 pm
MDW
-
PUJ
2 stops19h 12m
Delta
Thu 10/14:00 pm
PUJ
-
MDW
2 stops18h 07m
Delta
Deal found 7/23$385
This Delta deal was found by Cheapflights users on 7/23. 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.
Sat 9/262:00 pm
MDW
-
PUJ
2 stops21h 42m
Delta
Wed 9/304:00 pm
PUJ
-
MDW
2 stops18h 07m
Delta
Deal found 7/23$418
This Southwest deal was found by Cheapflights users on 7/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:55 pm
MDW
-
PUJ
2 stops16h 25m
Southwest
Thu 10/11:25 pm
PUJ
-
MDW
2 stops10h 40m
Southwest
Deal found 7/21$432
This Delta deal was found by Cheapflights users on 7/23. 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 12/76:00 am
MDW
-
PUJ
1 stop6h 25m
Delta
Fri 12/112:40 pm
PUJ
-
MDW
1 stop9h 30m
Delta
Deal found 7/23$446
This Delta deal was found by Cheapflights users on 7/23. 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 9/226:05 am
MDW
-
PUJ
1 stop6h 20m
Delta
Thu 10/14:00 pm
PUJ
-
MDW
2 stops18h 07m
Delta
Deal found 7/23$455
This Kissandfly.com deal was found by Cheapflights users on 7/21. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:11 am
MDW
-
PUJ
1 stop7h 28m
KLM
Sat 9/54:04 pm
PUJ
-
MDW
1 stop7h 32m
KLM
Deal found 7/21$467
This Delta deal was found by Cheapflights users on 7/21. 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.
Fri 8/286:05 am
MDW
-
PUJ
1 stop6h 20m
Delta
Wed 9/21:10 pm
PUJ
-
MDW
1 stop10h 26m
Delta
Deal found 7/21$470
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:00 am
MDW
-
PUJ
1 stop7h 40m
Southwest
Thu 8/272:35 pm
PUJ
-
MDW
1 stop7h 25m
Southwest
Deal found 7/19$474
This Delta deal was found by Cheapflights users on 7/21. 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.
Wed 9/94:30 pm
MDW
-
PUJ
2 stops19h 12m
Delta
Wed 9/162:50 pm
PUJ
-
MDW
1 stop8h 54m
Delta
Deal found 7/21$475
This FlightHub deal was found by Cheapflights users on 7/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
-
PUJ
1 stop7h 16m
Frontier
Tue 8/113:31 pm
PUJ
-
MDW
1 stop19h 20m
Frontier
Deal found 7/19$481
This Frontier deal was found by Cheapflights users on 7/22. 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 8/296:05 am
MDW
-
PUJ
1 stop7h 22m
Frontier
Sat 9/53:37 pm
PUJ
-
MDW
1 stop8h 10m
Frontier
Deal found 7/22$482

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 July 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$380
(Southwest)

One-way from

$173
(Delta)

Popular in

June

Cheapest in

April

Average price

$760

Good round-trip deal

$578 or less

Good one-way deal

$338 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. 11% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Punta Cana.
Search Deals
Price to beat on a one-way 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 July 24, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/28

7:55 pm-1:20 pm

2 stops16h 25m

Punta Cana

Thu 10/1

1:25 pm-11:05 pm

2 stops10h 40m

$432

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/22

6:05 am-1:25 pm

1 stop6h 20m

Punta Cana

Thu 10/1

4:00 pm-9:07 am

2 stops18h 07m

$455
Quickest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/29

6:11 am-1:25 pm

1 stop6h 14m

Punta Cana

Sat 9/5

4:04 pm-10:36 pm

1 stop7h 32m

$490

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 8/24

6:05 am-1:25 pm

1 stop6h 20m

Punta Cana

Thu 8/27

2:50 pm-10:36 pm

1 stop8h 46m

$530

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/8

6:05 am-2:32 pm

1 stop7h 27m

Punta Cana

Sat 9/12

4:00 pm-9:07 am

2 stops18h 07m

$555

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 8/23

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Thu 8/27

1:45 pm-7:30 am

2 stops18h 45m

$579

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/1

1:18 pm-11:43 am

2 stops21h 25m

Punta Cana

Thu 8/13

1:10 pm-12:39 pm

2 stops24h 29m

$632

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 8/21

5:00 am-1:40 pm

1 stop7h 40m

Punta Cana

Fri 8/28

1:45 pm-9:30 pm

1 stop8h 45m

$635

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 10/22

8:55 pm-1:45 pm

2 stops15h 50m

Punta Cana

Tue 10/27

2:45 pm-9:20 pm

1 stop7h 35m

$642

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 9/25

6:05 am-2:32 pm

1 stop7h 27m

Punta Cana

Mon 9/28

4:00 pm-10:44 pm

1 stop7h 44m

$721

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $515). Flying from Chicago Midway Airport to Punta Cana in June is currently the most expensive (average of $1,285). 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 July 24, 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.

How much does it cost to fly round-trip from Chicago Midway Airport to Punta Cana?

Airfare is below average for this route at the moment.

Chicago Midway Airport to Punta Cana flights typically cost between $710 and $1,014 in August.
The cheapest round-trip price found within the last 5 days was $380 on Southwest (Aug 31-Sep 3).

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 July 24, 2026.
Get a feel of what it's like to fly with Southwest 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
4,236 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.6
Fair
2,772 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore 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 2 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 6h 20m. Fly via Southwest or Delta 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 $478 on this airline. An additional option worth looking into is Southwest, starting at $503. Users have found that Frontier is 46% 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 $483, our data indicates the cheapest price to be $145. The most popular route (Chicago Midway - Punta Cana), is priced around $395.

  • 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 $515). Flying from Chicago Midway Airport to Punta Cana in June is currently the most expensive (average of $1,285). 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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Alternative routes for Midway to Punta Cana

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

Top 2 airlines flying from Midway to Punta Cana

Discover the top 2 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 July 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$478Average$960FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$503Average$981FlexibilityNo cancel feeOn-time63%

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