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$108+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 September 19, 2025.

Round-trip from

$277
(Expedia)

One-way from

$108
(Mytrip)

Popular in

June

Cheapest in

May

Average price

$367

Good round-trip deal

$320 or less

Good one-way deal

$306 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. 15% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 19, 2025.

This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 pmPUJ - ORD
Nonstop5h 10mArajet
Sat 1/1010:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/17$277
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:47 amPUJ - ORD
Nonstop5h 10mArajet
Sat 1/1010:27 amORD - PUJ
Nonstop4h 45mArajet
Deal found 9/17$279
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Wed 11/121:21 pmPUJ - ORD
1 stop12h 21mSpirit Airlines
Mon 11/175:59 pmORD - PUJ
1 stop16h 17mSpirit Airlines
Deal found 9/18$289
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Wed 11/121:21 pmPUJ - ORD
1 stop12h 21mSpirit Airlines
Sun 11/165:59 pmORD - PUJ
1 stop16h 17mSpirit Airlines
Deal found 9/18$290
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Fri 11/71:21 pmPUJ - ORD
1 stop9h 39mSpirit Airlines
Mon 11/105:59 pmORD - PUJ
1 stop16h 17mSpirit Airlines
Deal found 9/18$295
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/24:57 pmPUJ - ORD
1 stop10h 06mSpirit Airlines
Sun 11/95:59 pmORD - PUJ
1 stop16h 17mSpirit Airlines
Deal found 9/18$299
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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.
Fri 10/33:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Sat 10/116:58 pmORD - PUJ
1 stop15h 44mSpirit Airlines
Deal found 9/19$318
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Sat 1/105:59 pmORD - PUJ
1 stop16h 17mMultiple Airlines
Deal found 9/17$336
This Expedia deal was found by Cheapflights users on 9/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Sat 1/105:59 pmORD - PUJ
1 stop16h 17mMultiple Airlines
Deal found 9/17$339
This eDestinos deal was found by Cheapflights users on 9/17. 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.
Thu 10/99:38 amPUJ - MDW
1 stop26h 49mMultiple Airlines
Wed 10/158:05 amMDW - PUJ
2 stops24h 27mMultiple Airlines
Deal found 9/17$444
This Gotogate deal was found by Cheapflights users on 9/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/21:24 pmPUJ - MDW
2 stops10h 39mFrontier
Sun 11/96:15 amMDW - PUJ
1 stop7h 12mFrontier
Deal found 9/18$545
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Sun 11/29:15 pmPUJ - MDW
2 stops20h 05mMultiple Airlines
Sun 11/94:15 pmMDW - PUJ
2 stops18h 15mMultiple Airlines
Deal found 9/18$692

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 September 19, 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

Wed 11/12

1:21 pm-11:42 pm

1 stop12h 21m

Chicago O'Hare Intl

Sun 11/16

5:59 pm-12:16 pm

1 stop16h 17m

$290

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 10/3

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

Sat 10/11

6:58 pm-11:42 am

1 stop15h 44m

$318

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sun 12/21

6:00 pm-9:10 pm

Nonstop5h 10m

Chicago O'Hare Intl

Sat 1/10

5:59 pm-12:16 pm

1 stop16h 17m

$336

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Mon 11/17

9:30 am-4:02 pm

Nonstop4h 32m

$379

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

2:55 pm-6:08 pm

Nonstop5h 13m

Chicago O'Hare Intl

Sun 11/16

8:50 am-5:25 pm

1 stop6h 35m

$381

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 12/20

5:47 am-8:57 am

Nonstop5h 10m

Chicago O'Hare Intl

Sat 1/10

8:15 am-9:24 pm

2 stops11h 09m

$386

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 2/19

5:20 pm-11:43 pm

1 stop8h 23m

Chicago O'Hare Intl

Mon 2/23

9:30 am-4:02 pm

Nonstop4h 32m

$391

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 11/12

3:35 pm-11:18 am

1 stop21h 43m

Chicago O'Hare Intl

Sun 11/16

3:30 am-10:15 am

Nonstop4h 45m

$393

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$396

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 10/9

9:38 am-11:27 am

1 stop26h 49m

Chicago Midway

Wed 10/15

8:05 am-9:32 am

2 stops24h 27m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 35 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 September 19, 2025.

It’s typically best to fly out from Punta Cana to Chicago in the evening. Doing so could potentially save you 26% on the flight price compared to flying in the afternoon, which is usually more expensive.

How much does it cost to fly round-trip from Punta Cana to Chicago?

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 September 19, 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
8,926 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

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
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

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
3,171 reviews
United Airlines
7.4
Good
8,926 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Crew

8.1

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 0 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 10h 39m. There are 1967 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 $224 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 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 $122 on Arajet. Other airlines that offer cheap prices include Frontier from $131 and Spirit Airlines from $164 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 (81%), Frontier (61%) or United Airlines (37%) 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 $346, our data indicates the cheapest price to be $216. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $266.

  • 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.
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Santo Domingo to Midway flights
Santiago de los Caballeros to O'Hare Intl flights
Punta Cana to Midway 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$439FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$269Average$433FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$354Average$507FlexibilityNo cancel feeOn-time71%

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