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Punta Cana

$160+ 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
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$343
(Delta)

One-way from

$160
(Delta)

Popular in

December

Cheapest in

August

Average price

$620

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. 20% potential increase in price ($186 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 11/106:00 amMDW - PUJ
1 stop6h 23mDelta
Fri 11/143:50 pmPUJ - MDW
1 stop7h 54mDelta
Deal found 7/27$343
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Sat 8/99:12 pmMDW - PUJ
2 stops43h 03mFrontier
Tue 8/123:25 pmPUJ - MDW
1 stop20h 15mFrontier
Deal found 7/28$352
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:00 amMDW - PUJ
1 stop8h 30mSouthwest
Wed 10/81:40 pmPUJ - MDW
1 stop9h 55mSouthwest
Deal found 7/27$368
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:51 amMDW - PUJ
1 stop23h 50mMultiple Airlines
Sat 9/2712:36 pmPUJ - MDW
1 stop21h 42mMultiple Airlines
Deal found 7/27$437

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 29, 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

Mon 11/10

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Fri 11/14

3:50 pm-9:44 pm

1 stop7h 54m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/9

9:12 pm-5:15 pm

2 stops43h 03m

Punta Cana

Tue 8/12

3:25 pm-10:40 am

1 stop20h 15m

$352

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/3

5:00 am-2:30 pm

1 stop8h 30m

Punta Cana

Wed 10/8

1:40 pm-10:35 pm

1 stop9h 55m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 9/20

10:51 am-11:41 am

1 stop23h 50m

Punta Cana

Sat 9/27

12:36 pm-9:18 am

1 stop21h 42m

$437

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 10/27

5:04 pm-12:32 pm

2 stops18h 28m

$160

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/30

6:10 am-2:19 pm

1 stop7h 09m

$161

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 9/5

9:48 am-11:41 am

1 stop24h 53m

$179

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 9/26

5:10 am-2:05 pm

1 stop7h 55m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 $594). 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 29, 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.

What’s the top layover airport for flights from Chicago Midway Airport to Punta Cana?

Share of 1-stop round-trip flights from Chicago Midway Airport to Punta Cana chosen by Cheapflights users in the past 12 months, using the same layover each way.

Baltimore (BWI) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago Midway Airport to Punta Cana on Cheapflights.

What’s the cheapest layover airport for flights from Chicago Midway Airport to Punta Cana?

Average round-trip fare for 1-stop flights from Chicago Midway Airport to Punta Cana, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $606.

What’s the fastest layover option from Chicago Midway Airport to Punta Cana?

Shortest average travel time for 1-stop one-way flights from Chicago Midway Airport to Punta Cana, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 00m.

Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Punta Cana?

Average layover duration for 1-stop one-way flights from Chicago Midway Airport to Punta Cana, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.

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 29, 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

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 Delta. Our recent data shows that you can find tickets from as low as $343 on this airline. Additional options worth looking into are Frontier and Southwest, starting at $352 and $368 round-trip. Users have found that Delta is 52% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Punta Cana one-way?

    $160 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Frontier and Southwest, with prices starting from $161 and $185, respectively.

  • 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 $343.

  • 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 $594). 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?

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%
DeltaCheapest$539Average$802FlexibilityNo cancel feeOn-timeN/A

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