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$127+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This Orbitz deal was found by Cheapflights users on 11/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 11/2910:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 11/4$245
This Priceline deal was found by Cheapflights users on 11/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Tue 12/307:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/4$247
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Tue 12/27:00 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 11/2$249
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Mon 12/296:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Mon 1/55:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 11/4$255
This Orbitz deal was found by Cheapflights users on 11/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:30 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Tue 12/237:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 11/4$256
This CheapOair deal was found by Cheapflights users on 11/2. 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.
Sun 11/236:00 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Sun 11/306:45 amORD - PUJ
Nonstop4h 34mMultiple Airlines
Deal found 11/2$260
This eDestinos deal was found by Cheapflights users on 11/2. 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.
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mArajet
Wed 12/35:45 amORD - PUJ
Nonstop4h 45mArajet
Deal found 11/2$261
This Orbitz deal was found by Cheapflights users on 11/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Wed 1/75:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 11/4$262
This Orbitz deal was found by Cheapflights users on 11/4. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Wed 12/315:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 11/4$264
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sat 12/135:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Sat 12/207:10 amORD - PUJ
Nonstop4h 37mMultiple Airlines
Deal found 11/4$265
This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:20 pmPUJ - ORD
1 stop18h 16mUnited Airlines
Tue 12/99:30 amORD - PUJ
Nonstop4h 32mUnited Airlines
Deal found 11/3$274
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sun 12/711:45 amPUJ - MDW
1 stop12h 45mMultiple Airlines
Sun 12/142:59 pmMDW - PUJ
1 stop28h 30mMultiple Airlines
Deal found 11/1$321

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 November 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$240
(Expedia)

One-way from

$127
(Cheapflightsfares)

Popular in

June

Cheapest in

May

Average price

$385

Good round-trip deal

$212 or less

Good one-way deal

$230 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
Search Deals
From Punta Cana to Chicago (CHI)
Search Deals
One-way flight from Punta Cana to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Punta Cana to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Punta Cana to Chicago (CHI).
Search Deals

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 November 4, 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

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 3/7

10:27 am-5:12 pm

Nonstop4h 45m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 5/2

5:47 am-9:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 5/9

11:27 am-5:12 pm

Nonstop4h 45m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 12/2

5:20 pm-11:43 pm

1 stop8h 23m

Chicago O'Hare Intl

Tue 12/9

7:35 pm-5:25 pm

1 stop19h 50m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 12/3

5:20 pm-3:24 pm

1 stop24h 04m

Chicago O'Hare Intl

Wed 12/10

8:45 am-5:25 pm

1 stop6h 40m

$274

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 12/5

12:56 pm-11:44 pm

1 stop12h 48m

Chicago O'Hare Intl

Fri 12/12

6:15 pm-5:25 pm

1 stop21h 10m

$303

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 12/4

5:20 pm-2:12 pm

1 stop22h 52m

Chicago O'Hare Intl

Thu 12/11

8:45 am-12:59 pm

1 stop26h 14m

$304

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 12/6

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Tue 12/9

9:30 am-4:02 pm

Nonstop4h 32m

$307

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 11/25

5:20 pm-11:43 pm

1 stop8h 23m

Chicago O'Hare Intl

Tue 12/2

7:35 pm-5:25 pm

1 stop19h 50m

$324

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-9:08 am

1 stop17h 57m

Chicago Midway

Sun 2/22

7:17 pm-3:56 pm

1 stop18h 39m

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 11/24

3:50 pm-11:40 pm

1 stop9h 50m

Chicago Midway

Mon 12/1

6:00 am-2:25 pm

1 stop6h 25m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 33 results
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Compare providers for flights from Punta Cana to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Punta Cana to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Punta Cana-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Punta Cana-Chicago flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Punta Cana-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Punta Cana-Chicago flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Punta Cana-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, December is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $126). Flying from Punta Cana to Chicago in September is currently the most expensive (average of $347). 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 November 4, 2025.

It’s typically best to fly out from Punta Cana to Chicago in the evening. Doing so could potentially save you 27% 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 November 4, 2025.

The most flights from PUJ to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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

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 November 4, 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
8,998 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.8
Fair
3,116 reviews
United Airlines
7.4
Good
8,998 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 3 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.

  • How long is the flight from Punta Cana to Chicago?

    Departing from Punta Cana to Chicago will take you 5h 10m. There are 1982 mi between Punta Cana and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $181 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $269 and $354 round-trip. Users have found that Frontier is 57% 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 $142 on Frontier. Other airlines that offer cheap prices include United Airlines from $148 and Delta from $189 one-way.

  • 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 $327, our data indicates the cheapest price to be $152. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $240.

  • 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, December is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $126). Flying from Punta Cana to Chicago in September is currently the most expensive (average of $347). 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
Porter
Benton Harbor

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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
Punta Cana to Midway flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$181Average$412FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$269Average$423FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$354Average$502FlexibilityNo cancel feeOn-time71%

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