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Punta Cana

$155+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$335
(Kiwi.com)

One-way from

$155
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$708

Good one-way deal

$126 or less
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. 17% potential increase in price ($158 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/2712:17 pmMDW - PUJ
1 stop8h 12mMultiple Airlines
Sat 11/19:38 amPUJ - MDW
1 stop12h 44mMultiple Airlines
Deal found 9/11$335
This Southwest deal was found by Cheapflights users on 9/9. 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.
Tue 11/45:05 amMDW - PUJ
1 stop7h 55mSouthwest
Fri 11/144:05 pmPUJ - MDW
1 stop8h 55mSouthwest
Deal found 9/9$357
This Southwest deal was found by Cheapflights users on 9/10. 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.
Mon 10/275:00 amMDW - PUJ
1 stop8h 30mSouthwest
Fri 10/311:40 pmPUJ - MDW
2 stops18h 30mSouthwest
Deal found 9/10$359
This Delta deal was found by Cheapflights users on 9/9. 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 11/106:00 amMDW - PUJ
1 stop7h 38mDelta
Fri 11/145:03 pmPUJ - MDW
1 stop8h 29mDelta
Deal found 9/9$363
This Delta deal was found by Cheapflights users on 9/9. 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 12/295:59 pmMDW - PUJ
1 stop18h 27mDelta
Thu 1/85:11 pmPUJ - MDW
1 stop17h 43mDelta
Deal found 9/9$365
This Delta deal was found by Cheapflights users on 9/9. 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 11/106:48 pmMDW - PUJ
2 stops16h 25mDelta
Wed 11/192:38 pmPUJ - MDW
1 stop10h 54mDelta
Deal found 9/9$368
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:15 amMDW - PUJ
1 stop7h 07mMultiple Airlines
Sat 11/19:38 amPUJ - MDW
1 stop12h 44mMultiple Airlines
Deal found 9/10$379
This Southwest deal was found by Cheapflights users on 9/10. 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.
Mon 10/275:00 amMDW - PUJ
1 stop8h 30mSouthwest
Sat 11/12:25 pmPUJ - MDW
1 stop7h 35mSouthwest
Deal found 9/10$385
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:50 amMDW - PUJ
1 stop7h 10mSouthwest
Thu 12/42:40 pmPUJ - MDW
1 stop8h 25mSouthwest
Deal found 9/11$386
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:05 amMDW - PUJ
1 stop7h 05mSouthwest
Wed 10/293:10 pmPUJ - MDW
2 stops18h 10mSouthwest
Deal found 9/11$388
This Delta deal was found by Cheapflights users on 9/9. 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 11/106:00 amMDW - PUJ
1 stop6h 25mDelta
Tue 11/185:03 pmPUJ - MDW
1 stop8h 29mDelta
Deal found 9/9$389

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 September 11, 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 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

Thu 11/20

2:38 pm-11:32 pm

1 stop10h 54m

$389

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/10

6:00 am-2:25 pm

1 stop6h 25m

Punta Cana

Tue 11/18

5:03 pm-11:32 pm

1 stop8h 29m

$389

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 11/8

6:23 pm-1:26 pm

2 stops17h 03m

Punta Cana

Wed 11/19

2:38 pm-11:32 pm

1 stop10h 54m

$394

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 11/8

6:23 pm-1:26 pm

2 stops17h 03m

Punta Cana

Tue 11/18

5:03 pm-8:52 am

2 stops17h 49m

$394

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 9/27

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Sat 10/4

2:45 pm-9:10 pm

1 stop7h 25m

$413

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 12/9

6:40 am-3:10 pm

1 stop6h 30m

Punta Cana

Fri 12/12

4:05 pm-11:00 pm

1 stop8h 55m

$416

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 11/19

5:05 am-3:00 pm

1 stop7h 55m

Punta Cana

Wed 11/26

4:00 pm-11:50 pm

2 stops9h 50m

$425

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 12/28

6:00 pm-12:28 pm

1 stop16h 28m

Punta Cana

Thu 1/8

5:11 pm-8:54 am

1 stop17h 43m

$436

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/12

6:00 am-4:40 pm

1 stop8h 40m

Punta Cana

Wed 1/21

5:32 pm-8:50 am

2 stops17h 18m

$446

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 1/23

6:00 am-4:40 pm

1 stop8h 40m

Punta Cana

Wed 1/28

2:05 pm-9:46 pm

1 stop9h 41m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 21 results
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $443). Flying from Chicago Midway Airport to Punta Cana in June is currently the most expensive (average of $591). 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 September 11, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 60% on flights from Chicago Midway Airport to Punta Cana by exploring options for tickets at noon.

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 September 11, 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
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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 18m. 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 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 $146, our data indicates the cheapest price to be $126. 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $443). Flying from Chicago Midway Airport to Punta Cana in June is currently the most expensive (average of $591). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$495Average$743FlexibilityNo cancel feeOn-time63%
DeltaCheapest$539Average$802FlexibilityNo cancel feeOn-timeN/A

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