$152 Cheap Flights from Chicago (MDW) to Punta Cana (PUJ)

View $152 flight on Sat, Jan 10, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $152 for one-way flights and $327 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jan 10 - Sat, Jan 31
MDW
Chicago
PUJ
Punta Cana
$327 Roundtrip, found 23 hours ago
$327
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to Punta Cana, returning Sat, Jan 31, priced at $327 found 23 hours ago
Frontier Airlines
Sat, Jan 3 - Sat, Jan 31
MDW
Chicago
PUJ
Punta Cana
$328 Roundtrip, found 2 days ago
$328
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jan 3 from Chicago to Punta Cana, returning Sat, Jan 31, priced at $328 found 2 days ago
Frontier Airlines
Wed, Dec 31 - Sat, Jan 10
MDW
Chicago
PUJ
Punta Cana
$345 Roundtrip, found 9 hours ago
$345
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 31 from Chicago to Punta Cana, returning Sat, Jan 10, priced at $345 found 9 hours ago
Frontier Airlines
Sat, Jan 17 - Sat, Jan 31
MDW
Chicago
PUJ
Punta Cana
$346 Roundtrip, found 5 hours ago
$346
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Chicago to Punta Cana, returning Sat, Jan 31, priced at $346 found 5 hours ago
Frontier Airlines
Wed, Apr 8 - Sat, Apr 11
MDW
Chicago
PUJ
Punta Cana
$349 Roundtrip, just found
$349
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Apr 8 from Chicago to Punta Cana, returning Sat, Apr 11, priced at $349 just found
Frontier Airlines
Wed, Dec 31 - Sat, Jan 10
MDW
Chicago
PUJ
Punta Cana
$351 Roundtrip, found 9 hours ago
$351
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 31 from Chicago to Punta Cana, returning Sat, Jan 10, priced at $351 found 9 hours ago
Frontier Airlines
Sat, Jan 10 - Sat, Jan 17
MDW
Chicago
PUJ
Punta Cana
$357 Roundtrip, found 7 hours ago
$357
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to Punta Cana, returning Sat, Jan 17, priced at $357 found 7 hours ago
Frontier Airlines
Wed, Apr 8 - Sat, Apr 11
MDW
Chicago
PUJ
Punta Cana
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 8 from Chicago to Punta Cana, returning Sat, Apr 11, priced at $359 found 1 day ago
Southwest Airlines
Tue, Mar 10 - Mon, Mar 16
MDW
Chicago
PUJ
Punta Cana
$383 Roundtrip, found 2 days ago
$383
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Mar 10 from Chicago to Punta Cana, returning Mon, Mar 16, priced at $383 found 2 days ago
Delta
Mon, Jan 19 - Sat, Jan 24
MDW
Chicago
PUJ
Punta Cana
$394 Roundtrip, just found
$394
Roundtrip
just found
Select Delta flight, departing Mon, Jan 19 from Chicago to Punta Cana, returning Sat, Jan 24, priced at $394 just found

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

May is typically the cheapest month to fly

From $309 - $909 per traveler.

Alternative airports near Punta Cana

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

Select flight to Punta Cana Intl. PUJ. Cheapest and Closest option available. Average driving time to city center is 2 minutes. Flights from $508
PUJ
Punta Cana Intl.
CheapestClosest
Average driving time to city center2 min
Flights from $508

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ) cost?
Grab a cheap one-way flight from $152 or cheap return flight from $327 from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ) 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 Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
Flying in January is a good way to save, as it's the cheapest month for flights between MDW and PUJ. You'll usually find the lowest fares during off-peak months.
Which airlines fly direct from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
Hop on a nonstop flight with Southwest Airlines and go straight from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
To find the cheapest airline flying from MDW to PUJ, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
On average, Midway Intl. Airport (MDW) has 1 nonstop flights to Punta Cana Intl. Airport (PUJ) weekly. If you want more options, use Expedia's filters to discover flights with layovers. Squeeze in a visit to another city or simply break up your journey.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
More people fly between MDW and PUJ at 9 AM than at any other point in the day. Looking for a quieter experience? Travel outside of rush hours and you could save on your fare as well.
What day of the week has the most flights from MDW to PUJ?
If you depart on a Saturday, you'll get the biggest range of options for flights from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ).
What is the earliest flight from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
Take the earliest flight at around 9:35AM UTC-6, heading out of Midway Intl. Airport (MDW). You'll be flying for roughly 4h 25m, landing at Punta Cana Intl. Airport (PUJ) at approximately 4:00PM UTC-4.
How long does it take to fly from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
The average flight time from MDW to PUJ is 4 hours and 25 minutes, covering a total distance of 1,950 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
Book a flight from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**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 Punta Cana from Midway Intl. Airport (MDW)?
Punta Cana Intl. Airport (PUJ) is the only airport in Punta Cana with direct flights from Midway Intl. Airport (MDW). Compare your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ) last-minute?
Booking your ticket from MDW to PUJ right before your getaway is typically more expensive. But if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to PUJ flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to PUJ flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one place will take the hassle out of planning your trip. Simply pick your flights and choose from our wide range of hotels, then customize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Punta Cana Intl. Airport (PUJ)?
Typically, you're able to cancel or reschedule your MDW to PUJ flight. However, there may be additional charges, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you need more details, visit our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Punta Cana Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$327
Distance
1968 mi
Average flight time
4 hours 20 mins

Book with confidence

Chicago to Punta Cana Flights

The cheapest times to fly from Chicago to Punta Cana

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 Chicago to Punta Cana are during the month of January. You can find some of the cheapest flights from Chicago to Punta Cana with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Chicago to Punta Cana: 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 Chicago to Punta Cana

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 Chicago to Punta Cana in 2026. You can also book with separate airlines for your outbound and return journeys, from $152 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 Chicago to Punta Cana 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 Chicago to Punta Cana 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.

 

Chicago to Punta Cana Flights

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*Available to One Key members.