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Cheap Flights from Chicago to Puerto Plata

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 $1,162. Find the lowest prices on one-way and return tickets right here.
Puerto Plata.$919 per passenger.Departing Tue, 21 Jul, returning Tue, 28 Jul.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Tue, 21 Jul, arriving in Puerto Plata.Inbound indirect flight with Copa, departs from Puerto Plata on Tue, 28 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $919, select.
Puerto Plata.$931 per passenger.Departing Mon, 25 May, returning Fri, 5 Jun.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Mon, 25 May, arriving in Puerto Plata.Inbound indirect flight with Copa, departs from Puerto Plata on Fri, 5 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $931, select.
Puerto Plata.$1,080 per passenger.Departing Wed, 20 Jan, returning Mon, 25 Jan.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 20 Jan, arriving in Puerto Plata.Inbound indirect flight with United, departs from Puerto Plata on Mon, 25 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,080, select.
Puerto Plata.$1,132 per passenger.Departing Thu, 18 Jun, returning Sun, 21 Jun.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Thu, 18 Jun, arriving in Puerto Plata.Inbound indirect flight with Copa, departs from Puerto Plata on Sun, 21 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,132, select.
Puerto Plata.$1,162 per passenger.Departing Sat, 23 May, returning Sun, 31 May.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Sat, 23 May, arriving in Puerto Plata.Inbound indirect flight with United, departs from Puerto Plata on Sun, 31 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,162, select.
Puerto Plata.$1,166 per passenger.Departing Wed, 30 Dec, returning Fri, 8 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 30 Dec, arriving in Puerto Plata.Inbound indirect flight with Delta, departs from Puerto Plata on Fri, 8 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,166, select.
Puerto Plata.$7,131 per passenger.Departing Wed, 22 Apr, returning Tue, 28 Apr.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago Midway on Wed, 22 Apr, arriving in Puerto Plata.Inbound indirect flight with WestJet, departs from Puerto Plata on Tue, 28 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $7,131, select.

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 July.
Apr
from $7,131
May
from $1,162
Jun
from $1,132
Jul
from $919
Aug
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Sep
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Oct
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Nov
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Dec
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Jan
from $1,080
Feb
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Mar
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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.

Puerto Plata

14km from central Puerto Plata
Closest
from $919
Search flights

Santiago

37km from central Puerto Plata
Cheapest
from $531
Search flights

Chicago to Puerto Plata: Flight information

The things to know before you go.
Cheapest flight found$589
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 $919. 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 $919.
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, 21 July 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 .

Flying from Chicago to La Union Airport (POP): What you need to know

  • Chicago is home to a couple of airports that set the stage for your next getaway. Explore your options for reserving a flight from Chicago to La Union Airport (POP) heading out from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

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

  • To ensure you catch your flight from Chicago to POP, leave enough time to check in and drop off your luggage. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • With more people on the move during high season, plan to be at your terminal even earlier. Two hours for domestic flights and up to four for international trips will allow for extra wait times.

Airports in Chicago

O'Hare International Airport (ORD)

  • Stopovers are the perfect opportunity to take a travel break and possibly even visit a new city. When searching for cheap flights from Chicago to POP departing from O'Hare International Airport (ORD), deselect the 'Direct flights only' box to find out where you can visit along the way. Some popular options include:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Miami International Airport (MIA)

  • ORD is about 40 kilometres from central Chicago. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 35 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the journey time to be around 55 minutes.

  • Booked an early flight from Chicago to La Union Airport? Avoid the mad dash to the terminal (and sneak in some extra precious sleep) by picking one of these stays near O'Hare International Airport:

  • When it comes to the on-time performance of O'Hare International Airport, data shows 74.85% of flights complete their journey on time.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Tick a new place off your list or just take a moment to reset with a stopover. If you'd like to break up your flight from Chicago to La Union Airport, here's where you can stop when departing from Chicago Midway International Airport:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Charlotte Douglas International Airport (CLT)

    • Miami International Airport (MIA)

  • With public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 19 kilometres away, and making the trip by car will take approximately 20 minutes.

  • Kick off your holiday early with an additional night away from home. Before catching your Chicago to POP flight, stay in one of these hotels near Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure sheds light on how often flights that leave from this airport arrive on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From central Chicago, RFD is around 137 kilometres away. It takes roughly 1 hour 25 minutes to reach the airport by car and 4 hours 15 minutes or so if you take public transport.

  • Make catching an early Chicago to La Union Airport flight one of the easiest parts of your trip. Book a room at one of these accommodation options close to Chicago Rockford International Airport and head to your check-in counter feeling relaxed and unhurried:

  • Airports have an on-time performance rating that monitors how often flights arrive at their destinations without delays. At RFD, that rate is 76.19%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About La Union Airport (POP)

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

  • $589 is the lowest price for a one-way ticket from Chicago to La Union Airport. A return flight starts at $919. These prices can change depending on availability and demand.

  • To find cheap flights from Chicago to POP, book in advance. Airlines typically offer the most competitive fares when tickets are first released.

  • Cheap Chicago to La Union Airport tickets are easier to find if you're not locked into specific dates. Try using the 'Whole month' search tool to compare fares across every month and then choose the cheapest day.

  • Finding a cheap flight ticket from Chicago to POP is easy with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch as soon as a better deal is available.

  • Bag the best deal on a flight from Chicago to La Union Airport with the help of the filters. Pick your ideal departure and arrival times, number of stops and airlines. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest.'

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

  • Think about your travel style when planning your trip dates. May is the quietest month to visit Puerto Plata. March is when most people book flights from Chicago to La Union Airport (POP), which may be perfect if you're after more excitement.

  • The warmest month in Puerto Plata is August, with temperatures ranging between 23ºC and 31ºC. Book your Chicago to POP flight ticket then if that's your ideal forecast.

  • Search for cheap tickets from Chicago to La Union Airport in February if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging 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, check out our range of accommodation options including:

  • There are so many things to see and do in this city, it can be tricky to know where to begin. Long Beach, Golden Beach (Playa Dorada) and Teleferico Puerto Plata Cable Car are major attractions which should feature on every Puerto Plata itinerary.

Explore more of the Dominican Republic

  • You've done Puerto Plata, now it's time to explore more of the Dominican Republic. Travel around 161 kilometres south-east to Santo Domingo to check off its top attractions. From Alcazar de Colon to The Cathedral of the Americas and República Dominicana - Santo Domingod, you've got a jam-packed schedule ahead.

  • If you're interested in discovering another major stop in the Dominican Republic, consider Santo Domingo Este, roughly 161 kilometres south-east of Puerto Plata. Lago los tres ojos, Los Corales Park and National Aquarium are among the biggest draws.

More travel options

Plan the rest of your trip from Chicago to Puerto Plata

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