$188 Cheap Flights from Punta Cana (PUJ) to Chicago (MDW)

View $188 flight on Sat, Jan 31, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $188 for one-way flights and $363 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Nov 12 - Tue, Nov 18
PUJ
Punta Cana
MDW
Chicago
$363 Roundtrip, found 6 hours ago
$363
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Nov 12 from Punta Cana to Chicago, returning Tue, Nov 18, priced at $363 found 6 hours ago
Delta
Fri, Dec 12 - Sun, Dec 14
PUJ
Punta Cana
MDW
Chicago
$363 Roundtrip, just found
$363
Roundtrip
just found
Select Delta flight, departing Fri, Dec 12 from Punta Cana to Chicago, returning Sun, Dec 14, priced at $363 just found
Delta
Thu, Jan 15 - Sat, Jan 31
PUJ
Punta Cana
MDW
Chicago
$368 Roundtrip, found 10 hours ago
$368
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Jan 15 from Punta Cana to Chicago, returning Sat, Jan 31, priced at $368 found 10 hours ago
Delta
Thu, Jan 22 - Sun, Jan 25
PUJ
Punta Cana
MDW
Chicago
$370 Roundtrip, found 4 hours ago
$370
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Jan 22 from Punta Cana to Chicago, returning Sun, Jan 25, priced at $370 found 4 hours ago
Delta
Mon, Jan 12 - Sat, Jan 31
PUJ
Punta Cana
MDW
Chicago
$372 Roundtrip, found 10 hours ago
$372
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Jan 12 from Punta Cana to Chicago, returning Sat, Jan 31, priced at $372 found 10 hours ago
Delta
Tue, Dec 16 - Wed, Dec 31
PUJ
Punta Cana
MDW
Chicago
$378 Roundtrip, found 10 hours ago
$378
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Dec 16 from Punta Cana to Chicago, returning Wed, Dec 31, priced at $378 found 10 hours ago
Delta
Sat, Jan 17 - Tue, Jan 27
PUJ
Punta Cana
MDW
Chicago
$381 Roundtrip, found 10 hours ago
$381
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Jan 17 from Punta Cana to Chicago, returning Tue, Jan 27, priced at $381 found 10 hours ago
Southwest Airlines
Tue, Nov 4 - Mon, Nov 10
PUJ
Punta Cana
MDW
Chicago
$387 Roundtrip, found 11 hours ago
$387
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Punta Cana to Chicago, returning Mon, Nov 10, priced at $387 found 11 hours ago
Southwest Airlines
Fri, Nov 14 - Tue, Nov 18
PUJ
Punta Cana
MDW
Chicago
$392 Roundtrip, found 2 days ago
$392
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Punta Cana to Chicago, returning Tue, Nov 18, priced at $392 found 2 days ago
Frontier Airlines
Tue, Mar 31 - Tue, Apr 7
PUJ
Punta Cana
MDW
Chicago
$431 Roundtrip, found 5 days ago
$431
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Mar 31 from Punta Cana to Chicago, returning Tue, Apr 7, priced at $431 found 5 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 $292
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $292
Flights from Punta Cana (PUJ) to Chicago (MDW)
Origin airport
Punta Cana Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$362
Distance
1968 mi

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 November. 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 $188 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.

 

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 $188 or cheap return flight from $363 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)?
November 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.

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*Available to One Key members.