$167 Cheap Flights from Chicago (MDW) to Punta Cana (PUJ)

View $167 flight on Mon, Oct 27, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $167 for one-way flights and $355 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Oct 27 - Wed, Oct 29
MDW
Chicago
PUJ
Punta Cana
$355 Roundtrip, found 1 day ago
$355
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Punta Cana, returning Wed, Oct 29, priced at $355 found 1 day ago
Southwest Airlines
Sun, Oct 19 - Wed, Oct 22
MDW
Chicago
PUJ
Punta Cana
$355 Roundtrip, found 12 hours ago
$355
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sun, Oct 19 from Chicago to Punta Cana, returning Wed, Oct 22, priced at $355 found 12 hours ago
Southwest Airlines
Mon, Sep 29 - Fri, Oct 3
MDW
Chicago
PUJ
Punta Cana
$356 Roundtrip, found 15 hours ago
$356
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Mon, Sep 29 from Chicago to Punta Cana, returning Fri, Oct 3, priced at $356 found 15 hours ago
Delta
Mon, Oct 27 - Wed, Nov 5
MDW
Chicago
PUJ
Punta Cana
$356 Roundtrip, found 17 hours ago
$356
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Punta Cana, returning Wed, Nov 5, priced at $356 found 17 hours ago
Southwest Airlines
Sun, Dec 7 - Fri, Dec 12
MDW
Chicago
PUJ
Punta Cana
$357 Roundtrip, found 16 hours ago
$357
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Chicago to Punta Cana, returning Fri, Dec 12, priced at $357 found 16 hours ago
Southwest Airlines
Sun, Oct 19 - Wed, Oct 22
MDW
Chicago
PUJ
Punta Cana
$359 Roundtrip, found 12 hours ago
$359
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sun, Oct 19 from Chicago to Punta Cana, returning Wed, Oct 22, priced at $359 found 12 hours ago
Southwest Airlines
Tue, Sep 30 - Fri, Oct 3
MDW
Chicago
PUJ
Punta Cana
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 30 from Chicago to Punta Cana, returning Fri, Oct 3, priced at $360 found 1 day ago
Southwest Airlines
Tue, Oct 14 - Tue, Oct 21
MDW
Chicago
PUJ
Punta Cana
$361 Roundtrip, found 2 hours ago
$361
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Oct 14 from Chicago to Punta Cana, returning Tue, Oct 21, priced at $361 found 2 hours ago
Southwest Airlines
Mon, Nov 10 - Thu, Nov 13
MDW
Chicago
PUJ
Punta Cana
$363 Roundtrip, found 2 hours ago
$363
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Nov 10 from Chicago to Punta Cana, returning Thu, Nov 13, priced at $363 found 2 hours ago
Frontier Airlines
Sat, Oct 18 - Sat, Oct 25
MDW
Chicago
PUJ
Punta Cana
$403 Roundtrip, found 1 hour ago
$403
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Chicago to Punta Cana, returning Sat, Oct 25, priced at $403 found 1 hour ago

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

February is typically the cheapest month to fly

From $296 - $855 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 $389
PUJ
Punta Cana Intl.
CheapestClosest
Average driving time to city center2 min
Flights from $389
Flights from Chicago (MDW) to Punta Cana (PUJ)
Origin airport
Midway Intl.
Destination airport
Punta Cana Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$354
Distance
1968 mi

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 October. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $167 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.

 

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 $167 or cheap return flight from $355 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 October 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.

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*Available to One Key members.