HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$157+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Punta Cana to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$394
(Delta)

One-way from

$157
(Frontier)

Popular in

June

Cheapest in

May

Average price

$464

Good one-way deal

$282 or less
Provider with most accurate pricing for Punta Cana-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago Midway flights.
Search Deals
From Punta Cana to Chicago Midway
Search Deals
One-way flight from Punta Cana to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2025
Search Deals
Price to beat on a one-way flight from Punta Cana to Chicago Midway.
Search Deals

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 January 30, 2025.

This Delta deal was found by Cheapflights users on 1/30. 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 3/54:50 pmPUJ - MDW
1 stop7h 30mDelta
Wed 3/126:00 amMDW - PUJ
1 stop7h 32mDelta
Deal found 1/30$394
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/15:00 pmPUJ - MDW
Nonstop5h 00mSouthwest
Tue 2/45:35 amMDW - PUJ
1 stop7h 10mSouthwest
Deal found 1/29$598
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/611:55 pmPUJ - MDW
2 stops14h 15mMultiple Airlines
Fri 2/286:48 pmMDW - PUJ
1 stop13h 52mMultiple Airlines
Deal found 1/29$675
This LATAM Airlines deal was found by Cheapflights users on 1/28. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/132:45 amPUJ - MDW
2 stops20h 44mLATAM Airlines
Mon 4/211:05 pmMDW - PUJ
2 stops25h 10mLATAM Airlines
Deal found 1/28$2,355
This WestJet deal was found by Cheapflights users on 1/29. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/124:15 pmPUJ - MDW
2 stops26h 45mWestJet
Tue 5/201:05 pmMDW - PUJ
2 stops23h 38mWestJet
Deal found 1/29$3,524

Find flights from Punta Cana to Midway within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 3/5

4:50 pm-10:20 pm

1 stop7h 30m

Chicago Midway

Wed 3/12

6:00 am-2:32 pm

1 stop7h 32m

$394

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/27

2:20 pm-9:35 pm

1 stop9h 15m

Chicago Midway

Sun 3/2

6:25 am-3:10 pm

1 stop6h 45m

$603

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 2/12

10:50 pm-12:10 pm

1 stop15h 20m

Chicago Midway

Sat 2/15

7:55 pm-4:34 pm

2 stops18h 39m

$780

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sun 4/13

2:45 am-10:29 pm

2 stops20h 44m

Chicago Midway

Mon 4/21

1:05 pm-3:15 pm

2 stops25h 10m

$2,355

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 5/12

4:15 pm-6:00 pm

2 stops26h 45m

Chicago Midway

Tue 5/20

1:05 pm-1:43 pm

2 stops23h 38m

$3,524

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 3/17

2:15 pm-11:58 pm

1 stop10h 43m

$157

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 3/3

1:39 pm-3:12 pm

1 stop27h 33m

$186

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/23

1:03 pm-10:29 pm

1 stop10h 26m

$193

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sun 3/9

3:55 pm-8:10 pm

Nonstop5h 15m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Compare providers for flights from Punta Cana to Midway

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 Punta Cana to Midway in January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 Punta Cana-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Punta Cana-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Punta Cana-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Punta Cana-Chicago Midway Airport 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 Punta Cana-Chicago Midway Airport 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 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.

Travel insights for flights from Punta Cana to Midway

Get recent, data-driven insights about flights from Punta Cana to Midway including ideal travel times, pricing trends, and more.

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 January 30, 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 January 30, 2025.
To help decide which airline to fly from Punta Cana to Chicago, see what other customers have to say about Southwest, Delta and LATAM Airlines. 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
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,838 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,817 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.0
Okay
3,424 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($394), Southwest ($603), and LATAM Airlines ($2,355) offers the cheapest pricing from Punta Cana to Chicago Midway Airport.

  • 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 Frontier ($157), Delta ($193), and Southwest ($241).

  • 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 $543, our data indicates the cheapest price to be $223. The most popular route (Punta Cana - Chicago Midway), is priced around $353.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Punta Cana to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.