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Cheap flights from Chicago to Puerto Plata from $265

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Puerto Plata departing on 10/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Puerto Plata

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
1:45 pm - 10:31 pm
POP
-
ORD
9h 46m
1 stop
$628American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
8:46 pm - 12:15 pm
ORD
-
POP
14h 29m
2 stops
American Airlines Logo
1:45 pm - 11:53 pm
POP
-
ORD
11h 08m
2 stops
$633American Airlines
Fri, Oct 9 - Sat, Oct 17
Delta Logo
5:30 am - 3:55 pm
ORD
-
POP
8h 25m
1 stop
Delta Logo
5:10 pm - 11:50 pm
POP
-
ORD
8h 40m
1 stop
$638Delta
Sun, Nov 15 - Sun, Nov 22
American Airlines Logo
8:46 pm - 12:15 pm
ORD
-
POP
14h 29m
2 stops
American Airlines Logo
1:45 pm - 11:53 pm
POP
-
ORD
11h 08m
2 stops
$643American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
5:00 am - 12:46 pm
ORD
-
POP
6h 46m
1 stop
American Airlines Logo
1:36 pm - 11:44 pm
POP
-
ORD
11h 08m
2 stops
$648American Airlines
Mon, Aug 31 - Sun, Sep 6
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
2:55 pm - 11:08 pm
POP
-
ORD
10h 13m
1 stop
$661American Airlines
Mon, Oct 26 - Tue, Nov 10
American Airlines Logo
8:55 pm - 12:15 pm
ORD
-
POP
14h 20m
2 stops
American Airlines Logo
2:55 pm - 12:28 am
POP
-
ORD
11h 33m
2 stops
$666American Airlines
Mon, Oct 26 - Tue, Nov 10
American Airlines Logo
7:05 pm - 12:15 pm
ORD
-
POP
16h 10m
1 stop
American Airlines Logo
2:55 pm - 12:28 am
POP
-
ORD
11h 33m
2 stops
$671American Airlines
Wed, Oct 28 - Tue, Nov 10
American Airlines Logo
5:00 am - 12:15 pm
ORD
-
POP
6h 15m
1 stop
American Airlines Logo
2:55 pm - 11:02 am
POP
-
ORD
22h 07m
1 stop
$678American Airlines
Mon, Oct 26 - Tue, Nov 10
American Airlines Logo
5:00 am - 12:15 pm
ORD
-
POP
6h 15m
1 stop
American Airlines Logo
2:55 pm - 11:02 am
POP
-
ORD
22h 07m
1 stop
$688American Airlines
Mon, Oct 26 - Tue, Nov 10

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American Airlines flights from Chicago to Puerto Plata

Our best American Airlines deals on Chicago to Puerto Plata flight tickets
American Airlines
Oct 9
ORD7:05 pmChicago O'Hare Intl
16h 10m
1 stop
POP12:15 pmPuerto Plata La Union
Oct 17
POP1:45 pmPuerto Plata La Union
9h 46m
1 stop
ORD10:31 pmChicago O'Hare Intl
$628
American Airlines
Oct 9
ORD8:46 pmChicago O'Hare Intl
14h 29m
2 stops
POP12:15 pmPuerto Plata La Union
Oct 17
POP1:45 pmPuerto Plata La Union
11h 08m
2 stops
ORD11:53 pmChicago O'Hare Intl
$633
American Airlines
Oct 9
ORD8:46 pmChicago O'Hare Intl
14h 29m
2 stops
POP12:15 pmPuerto Plata La Union
Oct 17
POP1:45 pmPuerto Plata La Union
11h 08m
2 stops
ORD11:53 pmChicago O'Hare Intl
$643

JetBlue flights from Chicago to Puerto Plata

Our best JetBlue deals on Chicago to Puerto Plata flight tickets
JetBlue
Aug 18
ORD6:00 amChicago O'Hare Intl
7h 10m
1 stop
POP2:10 pmPuerto Plata La Union
Aug 22
POP12:30 pmPuerto Plata La Union
22h 36m
1 stop
ORD10:06 amChicago O'Hare Intl
$804
JetBlue
Aug 17
ORD6:00 amChicago O'Hare Intl
7h 10m
1 stop
POP2:10 pmPuerto Plata La Union
Aug 22
POP12:30 pmPuerto Plata La Union
22h 36m
1 stop
ORD10:06 amChicago O'Hare Intl
$841
JetBlue
Jul 17
ORD9:42 amChicago O'Hare Intl
27h 28m
1 stop
POP2:10 pmPuerto Plata La Union
Jul 25
POP12:00 pmPuerto Plata La Union
23h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
$847

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Puerto Plata that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 27, 2026.
Use the filters below to find and compare flights from Chicago to Puerto Plata that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Fri 10/9

7:05 pm-12:15 pm

1 stop16h 10m

Puerto Plata La Union

Sat 10/17

1:45 pm-10:31 pm

1 stop9h 46m

$628

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Fri 10/9

8:46 pm-12:15 pm

2 stops14h 29m

Puerto Plata La Union

Sat 10/17

1:45 pm-11:53 pm

2 stops11h 08m

$633
Quickest round-trip

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Sun 11/15

5:30 am-3:55 pm

1 stop8h 25m

Puerto Plata La Union

Sun 11/22

5:10 pm-11:50 pm

1 stop8h 40m

$638

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Fri 10/9

8:46 pm-12:15 pm

2 stops14h 29m

Puerto Plata La Union

Sat 10/17

1:45 pm-11:53 pm

2 stops11h 08m

$643

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Mon 8/31

5:00 am-12:46 pm

1 stop6h 46m

Puerto Plata La Union

Sun 9/6

1:36 pm-11:44 pm

2 stops11h 08m

$648

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Mon 10/26

7:05 pm-12:15 pm

1 stop16h 10m

Puerto Plata La Union

Tue 11/10

2:55 pm-11:08 pm

1 stop10h 13m

$661

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Mon 10/26

8:55 pm-12:15 pm

2 stops14h 20m

Puerto Plata La Union

Tue 11/10

2:55 pm-12:28 am

2 stops11h 33m

$666

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Wed 10/28

7:05 pm-12:15 pm

1 stop16h 10m

Puerto Plata La Union

Tue 11/10

2:55 pm-12:28 am

2 stops11h 33m

$671

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Mon 10/26

5:00 am-12:15 pm

1 stop6h 15m

Puerto Plata La Union

Tue 11/10

2:55 pm-11:02 am

1 stop22h 07m

$678

ChicagoPuerto Plata

ORD - POP

ORDPOP

Chicago O'Hare Intl

Mon 10/26

5:00 am-12:15 pm

1 stop6h 15m

Puerto Plata La Union

Tue 11/10

2:55 pm-11:02 am

1 stop22h 07m

$688

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Puerto Plata from

How to get the cheapest flight ticket from Chicago to Puerto Plata

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Puerto Plata?

In general, February is the cheapest month to fly from Chicago to Puerto Plata. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $182. If you’re not able to fly to Puerto Plata in February, then June is your next best option. Flight prices from Chicago to Puerto Plata during June average around $241.

Can stopping save me money on Chicago to Puerto Plata flights?

You could potentially save up to 7% on your flight if you consider stops on a Chicago to Puerto Plata flight.

Cheap Chicago to Puerto Plata flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Puerto Plata

Fastest flight time

7h 10m

Direct flights

None
The fastest flight from Chicago to Puerto Plata takes 7h 10m
There are no direct flights from Chicago to Puerto Plata. There are no popular flight routes from Chicago to Puerto Plata.
Search flight deals

Frequently asked questions about flying from Chicago to Puerto Plata

  • When did momondo last update prices for flights from Chicago to Puerto Plata?

    Prices for flights from Chicago to Puerto Plata are updated daily.

  • How many operators does momondo search for flights from Chicago to Puerto Plata?

  • How old do you have to be to fly from Chicago to Puerto Plata?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Puerto Plata.

  • What documentation or ID do you need to fly to Puerto Plata?

    The required travel and health documents for your Puerto Plata trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Puerto Plata. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Puerto Plata

Compare and see reviews for airlines that fly from Chicago to Puerto Plata with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $357Free CancellationRating
7.8
8,451 reviews
Search Delta flights
American AirlinesPriceFrom $387Free CancellationRating
7.1
11,779 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Puerto Plata?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Puerto Plata from Chicago.

Can I find flights from Chicago to Puerto Plata with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Puerto Plata from Chicago with this policy.

How can momondo help me find flights from Chicago to Puerto Plata?

Once all potential Chicago to Puerto Plata flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Puerto Plata right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Puerto Plata from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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