$192 Cheap Flights from Punta Cana (PUJ) to Chicago (MDW)

View $192 flight on Fri, Oct 31, 2025Opens in a new window

Popular airlines from Punta Cana Intl. Airport (PUJ) to Chicago Midway Airport (MDW)

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Cheap Flights from Punta Cana to Chicago (PUJ-MDW)

Prices were available within the past 7 days and start at $192 for one-way flights and $362 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Oct 31 - Mon, Nov 3
PUJ
Punta Cana
MDW
Chicago
$362 Roundtrip, found 2 days ago
$362
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 31 from Punta Cana to Chicago, returning Mon, Nov 3, priced at $362 found 2 days ago
Delta
Fri, Nov 14 - Mon, Nov 17
PUJ
Punta Cana
MDW
Chicago
$363 Roundtrip, found 5 hours ago
$363
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Nov 14 from Punta Cana to Chicago, returning Mon, Nov 17, priced at $363 found 5 hours ago
Southwest Airlines
Thu, Nov 6 - Tue, Nov 11
PUJ
Punta Cana
MDW
Chicago
$365 Roundtrip, found 3 days ago
$365
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Nov 6 from Punta Cana to Chicago, returning Tue, Nov 11, priced at $365 found 3 days ago
Delta
Sat, Nov 15 - Mon, Nov 17
PUJ
Punta Cana
MDW
Chicago
$369 Roundtrip, found 2 days ago
$369
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 15 from Punta Cana to Chicago, returning Mon, Nov 17, priced at $369 found 2 days ago
Southwest Airlines
Thu, Dec 18 - Tue, Dec 30
PUJ
Punta Cana
MDW
Chicago
$372 Roundtrip, found 4 days ago
$372
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Dec 18 from Punta Cana to Chicago, returning Tue, Dec 30, priced at $372 found 4 days ago
Southwest Airlines
Wed, Dec 24 - Sat, Jan 3
PUJ
Punta Cana
MDW
Chicago
$380 Roundtrip, found 4 days ago
$380
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 24 from Punta Cana to Chicago, returning Sat, Jan 3, priced at $380 found 4 days ago
Southwest Airlines
Fri, Oct 24 - Tue, Oct 28
PUJ
Punta Cana
MDW
Chicago
$384 Roundtrip, found 2 days ago
$384
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Oct 24 from Punta Cana to Chicago, returning Tue, Oct 28, priced at $384 found 2 days ago
Southwest Airlines
Fri, Oct 31 - Mon, Nov 3
PUJ
Punta Cana
MDW
Chicago
$385 Roundtrip, found 2 days ago
$385
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Punta Cana to Chicago, returning Mon, Nov 3, priced at $385 found 2 days ago
Southwest Airlines
Sat, Nov 22 - Sat, Nov 29
PUJ
Punta Cana
MDW
Chicago
$386 Roundtrip, found 6 days ago
$386
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Punta Cana to Chicago, returning Sat, Nov 29, priced at $386 found 6 days ago
Frontier Airlines
Sat, Oct 18 - Sat, Oct 25
PUJ
Punta Cana
MDW
Chicago
$429 Roundtrip, found 3 days ago
$429
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Punta Cana to Chicago, returning Sat, Oct 25, priced at $429 found 3 days ago

Find the cheapest month to fly from Punta Cana (PUJ) to Chicago (MDW)

February is typically the cheapest month to fly

From $348 - $867 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $408
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $408

Frequently asked questions

How much does a flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $192 or cheap return flight from $362 from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
October is the cheapest month to fly from PUJ to MDW. Timing your trip outside of the busy season is often the key to landing a great deal.
Which airlines fly direct from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Take a direct flight with Southwest Airlines and head straight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from PUJ to MDW, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
On average you can take your pick of 1 direct weekly flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW). For greater flexibility, consider flights with layovers. Just enter your details on Expedia and then filter your search results to show one or two stops.
What are the most popular departure times for flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Flights between PUJ and MDW tend to be busiest at 5 PM. If you want a more relaxed atmosphere and potentially cheaper tickets, choose a departure that's outside typical rush times.
What day of the week has the most flights from PUJ to MDW?
Saturday has the most flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW). Consider jetting off on this day and you'll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
The earliest flight taking off from Punta Cana Intl. Airport (PUJ) is at around 5:00PM UTC-4. Catch this flight and you'll reach Midway Intl. Airport (MDW) at approximately 8:00PM UTC-6. The total flight duration is 5h.
How long does it take to fly from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
It usually takes 5 hours to fly the 1,950 mi from PUJ to MDW.
What is the best time to fly from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Select a flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Punta Cana Intl. Airport (PUJ)?
If you're traveling on a direct flight from Punta Cana Intl. Airport (PUJ) to Chicago, you can arrive at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from PUJ to MDW are usually more expensive. To lock in the cheapest rates, start looking for flights as early as possible. That said, if you're flexible with your travel plans, you may land a cheap ticket just before your departure.
Is it cheaper to book a PUJ to MDW flight and hotel package?
Opting for a PUJ to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our wide range of accommodations and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Typically, you're able to cancel or reschedule your PUJ to MDW flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you'd like further information, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Punta Cana Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$362
Distance
1968 mi

Book with confidence

Book with confidence

Punta Cana to Chicago Flights

The cheapest times to fly from Punta Cana to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Punta Cana to Chicago are during the month of October. You can find some of the cheapest flights from Punta Cana to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Punta Cana to Chicago

Sunday is one of the best days to book for cheap flights from Punta Cana to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Punta Cana to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Punta Cana to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $192 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Punta Cana to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Punta Cana to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Punta Cana to Chicago Flights

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Explore a world of travel with Expedia

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