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$146+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$422
(Booking.com)

One-way from

$146
(Southwest)

Popular in

March

Cheapest in

August

Average price

$443

Good one-way deal

$320 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. 22% potential increase in price ($178 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($78 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/153:24 pmPUJ - MDW
1 stop20h 16mFrontier
Tue 8/511:39 amMDW - PUJ
1 stop25h 31mFrontier
Deal found 6/10$422
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/192:40 pmPUJ - MDW
1 stop8h 09mDelta
Wed 8/276:00 amMDW - PUJ
1 stop7h 34mDelta
Deal found 6/10$452
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 6/182:45 pmPUJ - MDW
1 stop10h 00mSouthwest
Sat 6/218:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Deal found 6/10$479
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Thu 7/1012:40 pmPUJ - MDW
1 stop8h 42mMultiple Airlines
Thu 7/179:12 pmMDW - PUJ
2 stops16h 18mMultiple Airlines
Deal found 6/10$512
This WestJet deal was found by Cheapflights users on 6/10. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1812:25 pmPUJ - MDW
2 stops30h 15mWestJet
Sat 6/211:47 pmMDW - PUJ
2 stops20h 01mWestJet
Deal found 6/10$3,577

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 June 12, 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

Tue 7/15

3:24 pm-10:40 am

1 stop20h 16m

Chicago Midway

Tue 8/5

11:39 am-2:10 pm

1 stop25h 31m

$422

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

2:40 pm-9:49 pm

1 stop8h 09m

Chicago Midway

Tue 8/26

6:00 am-1:15 pm

1 stop6h 15m

$452

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 7/10

12:40 pm-8:22 pm

1 stop8h 42m

Chicago Midway

Thu 7/17

9:12 pm-2:30 pm

2 stops16h 18m

$512

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

3:05 pm-8:55 am

2 stops18h 50m

Chicago Midway

Wed 8/27

6:25 am-2:05 pm

1 stop6h 40m

$559

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 7/15

12:25 pm-1:06 pm

2 stops25h 41m

Chicago Midway

Tue 8/5

1:46 pm-11:28 am

2 stops20h 42m

$3,620

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 7/12

3:20 pm-7:10 pm

Nonstop4h 50m

$146

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/30

2:42 pm-9:44 pm

1 stop8h 02m

$187

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sun 8/31

3:38 pm-11:27 pm

1 stop8h 49m

$191

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 8/8

1:01 pm-11:17 pm

2 stops11h 16m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 12, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
To help decide which airline to fly from Punta Cana to Chicago, see what other customers have to say about Southwest, Delta and WestJet. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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, Frontier ($422), Delta ($452), and Southwest ($559) offers the cheapest pricing from Punta Cana to Chicago Midway Airport. These flights start at 31% 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 Southwest ($146), Delta ($187), and Frontier ($191).

  • 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 $335, our data indicates the cheapest price to be $140. The most popular route (Punta Cana - Chicago Midway), is priced around $452.

  • 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 Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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