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Midway

$162+ Cheap flights from Punta Cana (PUJ) to Midway (MDW)

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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Punta Cana to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Punta Cana (PUJ) to Midway (MDW). 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

$350
(Delta)

One-way from

$162
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$1,090

Good one-way deal

$164 or less
From Punta Cana to Chicago Midway
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One-way flight from Punta Cana to Chicago Midway
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Highest demand for flights based on searches. 18% potential increase in price ($148 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($74 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 Punta Cana to Chicago Midway.
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Find flight deals from Punta Cana to Midway

Cheapest flights from Punta Cana to Midway
Explore the most affordable flight options available from Punta Cana to Midway. 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 7/29. 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 9/52:40 pmPUJ - MDW
1 stop7h 46mDelta
Sun 9/146:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 7/29$350
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:22 pmPUJ - MDW
1 stop8h 47mFrontier
Sat 10/186:10 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 7/29$391
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/273:05 pmPUJ - MDW
2 stops18h 00mSouthwest
Wed 9/36:15 amMDW - PUJ
1 stop6h 40mSouthwest
Deal found 7/28$431
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.
Wed 8/278:15 pmPUJ - MDW
2 stops21h 09mMultiple Airlines
Wed 9/39:35 amMDW - PUJ
2 stops27h 10mMultiple Airlines
Deal found 7/28$652
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:20 amPUJ - MDW
2 stops36h 17mWestJet
Thu 1/110:08 amMDW - PUJ
2 stops21h 48mWestJet
Deal found 7/27$1,571
This SmartFares deal was found by Cheapflights users on 7/26. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/92:45 amPUJ - MDW
2 stops31h 55mLATAM Airlines
Wed 9/176:30 pmMDW - PUJ
2 stops22h 45mLATAM Airlines
Deal found 7/26$2,564

Cheapflights Fare Finder

 
Customize your flight search to find flights from Punta Cana to Midway 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 Punta Cana to Chicago Midway Airport that are best for you.

Fly from

Punta Cana

Fly to

Midway

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 9/5

2:40 pm-9:26 pm

1 stop7h 46m

Chicago Midway

Sun 9/14

6:00 am-2:32 pm

1 stop7h 32m

$350

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 10/11

3:22 pm-11:09 pm

1 stop8h 47m

Chicago Midway

Sat 10/18

6:10 am-2:07 pm

1 stop6h 57m

$391

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/27

3:05 pm-8:05 am

2 stops18h 00m

Chicago Midway

Wed 9/3

6:15 am-1:55 pm

1 stop6h 40m

$431

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/27

8:15 pm-4:24 pm

2 stops21h 09m

Chicago Midway

Wed 9/3

9:35 am-1:45 pm

2 stops27h 10m

$652

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/9

2:45 am-9:40 am

2 stops31h 55m

Chicago Midway

Wed 9/17

6:30 pm-6:15 pm

2 stops22h 45m

$2,564

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/10

12:25 pm-1:03 pm

2 stops25h 38m

Chicago Midway

Wed 9/17

12:43 pm-10:49 am

2 stops21h 06m

$3,654

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 9/20

3:55 pm-8:39 am

1 stop17h 44m

$162

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 10/1

2:45 pm-9:36 pm

1 stop7h 51m

$192

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/28

3:05 pm-10:00 pm

1 stop7h 55m

$197

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 8/30

3:29 pm-11:08 pm

1 stop8h 39m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from Punta Cana to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Punta Cana 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 Punta Cana to Chicago Midway Airport

What is the cheapest time of day to fly from PUJ to MDW?

Find hourly flight availability from Punta Cana to Midway. 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.

When flying from Punta Cana to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and LATAM Airlines from Punta Cana to Chicago Midway Airport 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

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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.
LATAM Airlines
7.5
Good
1,821 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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.
WestJet
7.2
Good
2,973 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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 Punta Cana to Midway. 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 from for flights from Punta Cana to Chicago Midway?

    Punta Cana (PUJ) is the airport you will fly out of if you book a flight from Punta Cana to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Punta Cana; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Punta Cana airport to Chicago Midway. It is only a 9.2 mi journey to Punta Cana (PUJ) from Punta Cana’s city center.

  • What are the cheapest airlines flying from Punta Cana to Chicago Midway Airport round-trip?

    According to our current data, Delta ($350), Frontier ($391), and Southwest ($431) offers the cheapest pricing from Punta Cana to Chicago Midway Airport. These flights start at 46% lower than the current average price 3 months from now.

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

    The cheapest airlines for a one-way flight from Punta Cana to Chicago Midway Airport are Delta ($192), Southwest ($197), and Frontier ($200).

  • What are the cheapest flights from Punta Cana to Chicago Midway Airport?

    Looking for the cheapest flight from Punta Cana to Chicago Midway Airport? While on average our users pay $164, our data indicates the cheapest price to be $164. The most popular route (Punta Cana - Chicago Midway), is priced around $369.

  • Can I find deals for flights from Punta Cana to Midway that include hotel bookings?

    Yes. In addition to deals on Punta Cana to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Punta Cana to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Punta Cana to Midway.

  • Can I find deals for business class flights from Punta Cana to Midway?

    Yes. Cheapflights offers flight deals from Punta Cana to Midway 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 Punta Cana to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Punta Cana to Chicago Midway Airport (average of $160). Flying from Punta Cana to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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