$167 Cheap Flights from Chicago (MDW) to Puerto Plata (POP)

View $167 flight on Sun, Nov 16, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Gregorio Luperon Intl. Airport (POP)

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Puerto Plata (MDW-POP)

Prices were available within the past 7 days and start at $167 for one-way flights and $357 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Nov 19 - Wed, Dec 3
MDW
Chicago
POP
Puerto Plata
$357 Roundtrip, found 1 hour ago
$357
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Nov 19 from Chicago to Puerto Plata, returning Wed, Dec 3, priced at $357 found 1 hour ago
Delta
Wed, Nov 19 - Wed, Dec 3
MDW
Chicago
POP
Puerto Plata
$362 Roundtrip, found 1 hour ago
$362
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Nov 19 from Chicago to Puerto Plata, returning Wed, Dec 3, priced at $362 found 1 hour ago
Delta
Sun, Feb 22 - Mon, Mar 9
MDW
Chicago
POP
Puerto Plata
$372 Roundtrip, found 2 days ago
$372
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Feb 22 from Chicago to Puerto Plata, returning Mon, Mar 9, priced at $372 found 2 days ago
Delta
Sat, Feb 7 - Sat, Feb 14
MDW
Chicago
POP
Puerto Plata
$377 Roundtrip, found 4 hours ago
$377
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Feb 7 from Chicago to Puerto Plata, returning Sat, Feb 14, priced at $377 found 4 hours ago
Delta
Sat, Feb 21 - Mon, Mar 9
MDW
Chicago
POP
Puerto Plata
$387 Roundtrip, found 2 days ago
$387
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Feb 21 from Chicago to Puerto Plata, returning Mon, Mar 9, priced at $387 found 2 days ago
Delta
Wed, Mar 4 - Wed, Mar 11
MDW
Chicago
POP
Puerto Plata
$392 Roundtrip, found 17 hours ago
$392
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Mar 4 from Chicago to Puerto Plata, returning Wed, Mar 11, priced at $392 found 17 hours ago
Delta
Sun, Nov 16 - Mon, Nov 24
MDW
Chicago
POP
Puerto Plata
$435 Roundtrip, just found
$435
Roundtrip
just found
Select Delta flight, departing Sun, Nov 16 from Chicago to Puerto Plata, returning Mon, Nov 24, priced at $435 just found
Delta
Sun, Nov 16 - Mon, Nov 24
MDW
Chicago
POP
Puerto Plata
$440 Roundtrip, just found
$440
Roundtrip
just found
Select Delta flight, departing Sun, Nov 16 from Chicago to Puerto Plata, returning Mon, Nov 24, priced at $440 just found
Delta
Thu, Feb 19 - Mon, Mar 9
MDW
Chicago
POP
Puerto Plata
$450 Roundtrip, found 2 days ago
$450
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Feb 19 from Chicago to Puerto Plata, returning Mon, Mar 9, priced at $450 found 2 days ago
Delta
Wed, Mar 4 - Thu, Mar 12
MDW
Chicago
POP
Puerto Plata
$455 Roundtrip, found 17 hours ago
$455
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Mar 4 from Chicago to Puerto Plata, returning Thu, Mar 12, priced at $455 found 17 hours ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP) cost?
Snag a cheap one-way flight from $167 or cheap return flight from $357 from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP)?
November is the least expensive month to fly from MDW to POP. Traveling during quieter months is often the key to finding a great deal.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to POP. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP)?
Direct flights from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to POP?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary based on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP)?
To reach Gregorio Luperon Intl. Airport (POP) on schedule, select a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP) last-minute?
Last-minute fares from MDW to POP are usually more expensive. To lock in the lowest prices, start searching for flights as early as possible. That said, if you're flexible with your travel dates, it's possible to land a cheap ticket just before your departure.
Is it cheaper to book a MDW to POP flight and hotel package?
Securing a MDW to POP flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Choose from our extensive range of hotels and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Gregorio Luperon Intl. Airport (POP)?
In most cases, you can cancel or reschedule your MDW to POP flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you need further details, go to our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Gregorio Luperon Intl.
Airlines serving
Delta
Roundtrip price
$357
Distance
1824 mi

Book with confidence

Book with confidence

Chicago to Puerto Plata Flights

The cheapest times to fly from Chicago to Puerto Plata

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

 

The best time to book a flight from Chicago to Puerto Plata

Sunday is one of the best days to book for cheap flights from Chicago to Puerto Plata: 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 Puerto Plata

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 Puerto Plata 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 Puerto Plata 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 Puerto Plata 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 Puerto Plata Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.