C$468 Cheap Flights from Chicago (CHIA) to Puerto Plata (POP)

Compare Chicago to Puerto Plata flight deals

Find the cheapest month or even day of the year to fly to Puerto Plata

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Flight deals from Chicago to Puerto Plata

Looking for a cheap last-minute deal or the best return flight from Chicago to Puerto Plata Airport? If you want to travel next month, return fares start from C$939. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Puerto Plata

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Puerto Plata flights are currently cheapest in May.

Chicago to Puerto Plata: Alternative routes

Compare routes from Chicago to Puerto Plata below. You may find an airport to fly into that's cheaper, faster, or easier than Puerto Plata.

Chicago to Puerto Plata: Flight information

The things to know before you go.
Cheapest flight foundC$468
Cheapest month to flyMay

Finding cheap flights from Chicago to Puerto Plata: Frequently asked questions

The best price we found for a return flight from Chicago to Puerto Plata is C$706. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Puerto Plata. But we found flights with one stop from C$706.
As of April 2026, there are no flights flying from Chicago to Puerto Plata.
The cheapest month to fly from Chicago to Puerto Plata is usually July.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Puerto Plata Airport on Tuesday, July 21, 2026.
No airlines currently offer direct flights between Chicago and Puerto Plata Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Puerto Plata but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Puerto Plata is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Puerto Plata is Copa .

Travelling from Chicago to La Union Airport (POP): what you need to know

  • Chicago has a couple of airports where you can kick off your trip. Check out your options for reserving a flight from Chicago to La Union Airport (POP) leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • The timezone in Puerto Plata is UTC-4, which is 1 hour ahead of Chicago. La Union Airport is located in Puerto Plata.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to board your flight from Chicago to POP.

  • Flying during a peak time like August? Busy periods (like spring break, summer and New Year) can add another hour at check-in and security. Be extra safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • Think about adding a stopover to potentially find a cheaper flight from Chicago to POP. Just uncheck 'Direct flights only' when searching for departures from O'Hare International Airport (ORD). Take a pause at one of these airports:

    • Charlotte Douglas International Airport (CLT)

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Miami International Airport (MIA)

  • ORD is roughly 40 kilometres from central Chicago. To help work out how to get there, use Google Maps. This useful travel app will show you the best route and your public transport options.

  • Booked an early flight from Chicago to La Union Airport? Avoid the hassle of rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these stays close to O'Hare International Airport:

Chicago Midway International Airport (MDW)

  • Maximize your vacation with a stopover on your flight from Chicago to La Union Airport. Visit family or friends or tick a new city off your bucket list. Whatever you decide to do, check out these options between Chicago Midway International Airport and POP:

    • Charlotte Douglas International Airport (CLT)

    • Miami International Airport (MIA)

    • Pearson International Airport (YYZ)

  • You can reach MDW from the centre of Chicago in about 21 minutes by car (depending on traffic conditions). The journey on public transport will take roughly 46 minutes to cover the 19 kilometres or so.

  • You're off on vacation, so why not enjoy an additional night away? Think about checking in to one of these hotels near Chicago Midway International Airport the day before your flight from Chicago to POP:

About La Union Airport (POP)

Getting from La Union Airport (POP) to central Puerto Plata

  • La Union Airport is approximately 19 kilometres from the centre of Puerto Plata. With your own car rental or if you're catching a cab, the drive is around 28 minutes.

How to find the cheapest flights from Chicago to La Union Airport (POP)

  • The best price we've seen for a one-way ticket from Chicago to La Union Airport is C$468. The cheapest price for a return flight is C$706. Keep in mind fares can change due to demand at the time of booking.

  • It's usually smart to book ahead of time if you want to find flight tickets from Chicago to POP. That's because flight prices are based on demand, which tends to increase closer to the departure date.

  • If you're flexible with your travel plans, make the most of the 'Whole month' tool. It'll give you the lowest price in every month when searching for your ticket from Chicago to La Union Airport.

  • Log into your online account or use the app to create a Price Alert. We'll notify you straight away if there's a better deal on this route. It doesn't take long, and it'll save you the hassle of searching for flight tickets from Chicago to POP every day.

  • Use the filters to tailor your flights from Chicago to La Union Airport. Simply select your preferred departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest' to see the best deals.

The best time to fly from Chicago to La Union Airport (POP)

  • It's time to pick your trip dates for your flight from Chicago to La Union Airport. March is the busiest month for a trip to Puerto Plata. If you prefer a quieter atmosphere, go in May.

  • Lock in your flight from Chicago to POP for August if you're eager to experience the city during its warmest month. You can expect temperatures in Puerto Plata to range from 23ºC to 31ºC.

  • If you'd rather travel in cooler conditions, search for a cheap flight from Chicago to La Union Airport in February when temperatures average between 19ºC and 27ºC.

More about Puerto Plata

  • Start your Puerto Plata trip right by choosing the ideal place to stay. As soon as you've booked your flight from Chicago to La Union Airport, explore our selection of hotels including:

  • There are so many things to discover in this city it can be tricky to work out where to begin. Fortaleza San Felipe, Teleferico Puerto Plata Cable Car and Mount Isabel de Torres are top attractions which should be on any well-planned Puerto Plata itinerary.

Complete your Puerto Plata trip with a car rental

  • Finding you a cheap flight from Chicago to La Union Airport isn't the only thing we're good at. Check out our car rentals in Puerto Plata and see the sights your way. We search for deals from trusted car rental providers and put them all in one place. Instantly compare offers and then book with no fees.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.