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$117+ Cheap flights from Punta Cana (PUJ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheap flight deals from Punta Cana to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Punta Cana (PUJ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated agosto 14, 2025.

Round-trip from

$286
(Cheapflightsfares)

One-way from

$117
(Cheapflightsfares)

Popular in

June

Cheapest in

May

Average price

$399

Good round-trip deal

$360 or less

Good one-way deal

$198 or less
From Punta Cana to Chicago (CHI)
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One-way flight from Punta Cana to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Punta Cana to Chicago (CHI).
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Price to beat on a one-way flight from Punta Cana to Chicago (CHI).
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Find flight deals from Punta Cana to Chicago

Cheapest flights from Punta Cana to Chicago
Explore the most affordable flight options available from Punta Cana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/145:45 pmPUJ - ORD
Nonstop5h 08mFrontier
lun. 8/186:45 amORD - PUJ
Nonstop4h 40mFrontier
Deal found 8/12$285
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/303:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
sáb. 10/45:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Deal found 8/12$286
This eDestinos deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/63:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
sáb. 9/1311:57 amORD - PUJ
2 stops22h 48mSpirit Airlines
Deal found 8/12$309
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/63:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
dom. 9/145:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Deal found 8/12$318
This SmartFares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/253:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
mié. 10/111:57 amORD - PUJ
2 stops22h 48mSpirit Airlines
Deal found 8/12$324
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/155:08 pmPUJ - ORD
Nonstop5h 08mMultiple Airlines
vie. 8/293:07 pmORD - PUJ
1 stop10h 04mMultiple Airlines
Deal found 8/12$338
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/42:25 pmPUJ - MDW
1 stop7h 30mSouthwest
lun. 10/135:50 amMDW - PUJ
1 stop6h 55mSouthwest
Deal found 8/13$399
This Mytrip deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/1710:17 amPUJ - MDW
1 stop13h 07mFrontier
dom. 8/246:15 amMDW - PUJ
1 stop7h 08mFrontier
Deal found 8/13$455
This Mytrip deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/1511:20 amPUJ - MDW
1 stop13h 31mFrontier
jue. 8/216:15 amMDW - PUJ
1 stop7h 08mFrontier
Deal found 8/13$471
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/52:40 pmPUJ - MDW
1 stop8h 25mSouthwest
dom. 11/95:50 amMDW - PUJ
1 stop7h 10mSouthwest
Deal found 8/12$481
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/263:20 pmPUJ - MDW
2 stops26h 10mDelta
dom. 1/46:25 pmMDW - PUJ
1 stop16h 05mDelta
Deal found 8/12$512
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/263:20 pmPUJ - MDW
2 stops26h 10mDelta
vie. 1/26:00 amMDW - PUJ
1 stop8h 44mDelta
Deal found 8/12$541

Cheapflights Fare Finder

 
Customize your flight search to find flights from Punta Cana to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
Use the filters below to find and compare flights from Punta Cana to Chicago that are best for you.

Fly from

Punta Cana

Fly to

Chicago

Route

Depart

Return

Price

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 10/2

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

mar. 10/7

5:05 am-2:49 pm

1 stop8h 44m

$286

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 9/4

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

dom. 9/21

5:05 am-2:14 pm

1 stop8h 09m

$309

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

sáb. 9/6

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

sáb. 9/13

11:57 am-11:45 am

2 stops22h 48m

$311

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 9/25

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

mié. 10/1

11:57 am-11:45 am

2 stops22h 48m

$324

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mié. 10/15

3:57 pm-11:45 pm

1 stop8h 48m

Chicago O'Hare Intl

jue. 10/30

5:05 am-2:59 pm

1 stop8h 54m

$324

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

sáb. 9/6

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

dom. 9/14

5:05 am-2:14 pm

1 stop8h 09m

$335

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

sáb. 10/4

2:25 pm-8:55 pm

1 stop7h 30m

Chicago Midway

lun. 10/13

5:50 am-1:45 pm

1 stop6h 55m

$399

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

jue. 1/15

2:05 pm-9:46 pm

1 stop9h 41m

Chicago Midway

lun. 1/19

6:00 am-3:25 pm

1 stop7h 25m

$462

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

mié. 11/12

2:40 pm-9:05 pm

1 stop8h 25m

Chicago Midway

dom. 11/16

5:05 am-3:10 pm

1 stop8h 05m

$481

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

mié. 11/5

2:40 pm-9:05 pm

1 stop8h 25m

Chicago Midway

dom. 11/9

5:50 am-3:00 pm

1 stop7h 10m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 32 results
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The best insider tips for Punta Cana to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Punta Cana to Chicago trip
Airports
PUJ

Security lines at PUJ are efficient, typically under 20 minutes unless during peak times. Consider the VIP service for a faster experience.

Read more about PUJby Matt Meltzer
ORD

At ORD, expect long walks to immigration in Terminal 5. Consider the 'L' train for a quicker city transfer.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on PUJ

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Best time to book a flight from Punta Cana to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Punta Cana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Punta Cana to Chicago

What is the cheapest month to book a flight from Punta Cana to Chicago?

Currently, August is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $245). Flying from Punta Cana to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PUJ to CHI?

Find hourly flight availability from Punta Cana to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 14, 2025.

It’s typically best to fly out from Punta Cana to Chicago in the morning. Doing so could potentially save you 13% on the flight price compared to flying in the afternoon, which is usually more expensive.

Weekly flight availability from Punta Cana to Chicago

Explore weekly flight availability from Punta Cana to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated agosto 14, 2025.

The most flights from PUJ to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated agosto 14, 2025.
Get a feel of what it's like to fly with United Airlines and Frontier from Punta Cana to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,916 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,916 reviews
United Airlines
7.4
Good
8,916 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Frontier
5.8
Fair
3,217 reviews
United Airlines
7.4
Good
8,916 reviews

Crew

8.1

Comfort

7.3

Boarding

7.7

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Punta Cana to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Punta Cana to Chicago?

    Punta Cana (PUJ) is the airport you will fly out of if you book a flight from Punta Cana to Chicago. You should not have trouble finding flights to Chicago from Punta Cana; the airport handles an average of 2 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Punta Cana airport to Chicago. It is only a 9.2 mi journey to Punta Cana (PUJ) from Punta Cana’s city center.

  • What are the cheapest airlines flying from Punta Cana to Chicago round-trip?

    Our cheapest airline available from Punta Cana to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $224 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $312 and $384 round-trip. Users have found that Frontier is 45% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Punta Cana to Chicago one-way?

    One-way options have recently been found by users for as low as $117 on Arajet. Other airlines that offer cheap prices include Spirit Airlines from $127 and Delta from $192 one-way.

  • What are the most reliable airlines from Punta Cana to Chicago?

    No one likes to see their flight delayed. When booking a flight from Punta Cana to Chicago consider choosing American Airlines (85%), United Airlines (84%) or Frontier (67%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Punta Cana to Chicago?

    Looking for the cheapest flight from Punta Cana to Chicago? While on average our users pay $364, our data indicates the cheapest price to be $159. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $305.

  • Can I find deals for flights from Punta Cana to Chicago that include hotel bookings?

    Yes. In addition to deals on Punta Cana to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Punta Cana to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Punta Cana to Chicago.

  • Can I find deals for business class flights from Punta Cana to Chicago?

    Yes. Cheapflights offers flight deals from Punta Cana to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Punta Cana to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $245). Flying from Punta Cana to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Punta Cana to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Santiago de los Caballeros to O'Hare Intl flights

Top 3 airlines flying from Punta Cana to Chicago

Discover the top 3 airlines that operate flights from Punta Cana to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$439FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$384Average$507FlexibilityNo cancel feeOn-time71%

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