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$185+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
May 10 — May 171
Sun 5/10
Sun 5/17
1 adult, Economy
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Cheap 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 April 10, 2026.

This Expedia deal was found by Cheapflights users on 4/8. 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 5/93:35 pm
PUJ
-
ORD
1 stop17h 20m
Frontier
Sat 5/167:52 pm
ORD
-
PUJ
1 stop14h 05m
Frontier
Deal found 4/8$263
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Fri 5/13:54 pm
PUJ
-
ORD
1 stop9h 30m
Spirit Airlines
Mon 5/45:05 am
ORD
-
PUJ
1 stop7h 25m
Spirit Airlines
Deal found 4/7$264
This Priceline deal was found by Cheapflights users on 4/9. 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.
Fri 5/13:54 pm
PUJ
-
ORD
1 stop9h 30m
Spirit Airlines
Mon 5/115:05 am
ORD
-
PUJ
1 stop7h 25m
Spirit Airlines
Deal found 4/9$282
This Frontier deal was found by Cheapflights users on 4/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:37 pm
PUJ
-
MDW
2 stops9h 49m
Frontier
Sun 5/106:00 am
MDW
-
PUJ
1 stop7h 24m
Frontier
Deal found 4/9$288
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fri 5/13:54 pm
PUJ
-
ORD
1 stop9h 00m
Multiple Airlines
Sun 5/105:05 am
ORD
-
PUJ
1 stop7h 25m
Multiple Airlines
Deal found 4/9$305
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Fri 5/19:13 pm
PUJ
-
ORD
2 stops19h 10m
Multiple Airlines
Mon 5/45:05 am
ORD
-
PUJ
1 stop7h 25m
Multiple Airlines
Deal found 4/7$308
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Wed 4/229:13 pm
PUJ
-
ORD
1 stop24h 36m
Multiple Airlines
Fri 5/155:30 pm
ORD
-
PUJ
1 stop14h 48m
Multiple Airlines
Deal found 4/6$312
This Expedia deal was found by Cheapflights users on 4/9. 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.
Fri 5/13:54 pm
PUJ
-
ORD
1 stop9h 30m
Multiple Airlines
Mon 5/114:30 am
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Deal found 4/9$313
This Expedia deal was found by Cheapflights users on 4/8. 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 4/183:04 pm
PUJ
-
ORD
1 stop8h 35m
Frontier
Fri 5/85:30 pm
ORD
-
PUJ
1 stop14h 48m
Frontier
Deal found 4/8$315
This Booking.com deal was found by Cheapflights users on 4/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:29 pm
PUJ
-
ORD
1 stop26h 17m
Frontier
Sat 5/307:52 pm
ORD
-
PUJ
1 stop14h 05m
Frontier
Deal found 4/8$317
This Frontier deal was found by Cheapflights users on 4/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:37 pm
PUJ
-
ORD
2 stops10h 02m
Frontier
Tue 5/53:55 pm
ORD
-
PUJ
2 stops17h 40m
Frontier
Deal found 4/8$321
This Trip.com deal was found by Cheapflights users on 4/8. 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.
Sat 4/1811:07 am
PUJ
-
MDW
1 stop21h 52m
Frontier
Fri 5/84:52 pm
MDW
-
PUJ
1 stop15h 26m
Frontier
Deal found 4/8$328

Find 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 April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$263
(Expedia)

One-way from

$185
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$402

Good round-trip deal

$380 or less

Good one-way deal

$259 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. 14% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 10, 2026.
Use the filters below to find and compare flights from Punta Cana to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 5/5

9:30 am-3:12 pm

Nonstop4h 42m

$327

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

1:37 pm-10:26 pm

2 stops9h 49m

Chicago Midway

Mon 5/11

4:52 pm-10:35 am

2 stops16h 43m

$347

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

9:13 pm-4:13 pm

2 stops20h 00m

Chicago Midway

Tue 5/5

6:00 am-8:19 pm

2 stops13h 19m

$400

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Mon 6/8

5:25 pm-10:18 am

1 stop17h 53m

Chicago O'Hare Intl

Sat 6/13

7:52 pm-10:58 am

1 stop14h 06m

$443

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/13

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 9/8

9:40 pm-12:40 pm

1 stop14h 00m

$449

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/13

2:20 pm-1:27 am

1 stop12h 07m

Chicago O'Hare Intl

Sun 9/6

9:40 pm-12:40 pm

1 stop14h 00m

$454

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 5/1

1:50 pm-5:59 pm

Nonstop5h 09m

Chicago O'Hare Intl

Mon 5/4

9:30 am-3:12 pm

Nonstop4h 42m

$468

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

3:57 pm-10:28 pm

1 stop7h 31m

Chicago Midway

Tue 5/5

6:00 am-2:32 pm

1 stop7h 32m

$488

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 5/1

1:00 pm-10:28 pm

1 stop10h 28m

Chicago Midway

Sun 5/10

6:23 am-2:35 pm

1 stop7h 12m

$488

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/11

3:39 pm-11:09 am

1 stop20h 30m

Chicago Midway

Mon 6/15

6:00 am-2:25 pm

1 stop7h 25m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 28 resultsSorted by cheapest first
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Punta Cana-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, August is the cheapest month in which you can book a flight from Punta Cana to Chicago (average of $139). Flying from Punta Cana to Chicago in March is currently the most expensive (average of $537). 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 April 10, 2026.

It’s typically best to fly out from Punta Cana to Chicago in the evening. Doing so could potentially save you 53% on the flight price compared to flying at noon, 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 April 10, 2026.

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 (1 on average).

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

The best insider tips for Punta Cana to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Punta Cana to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 April 10, 2026.
Get a feel of what it's like to fly with American Airlines 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.
American Airlines
7.1
Good
11,564 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Overall

7.1

Crew

7.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,564 reviews
American Airlines
7.1
Good
11,564 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.8

Overall

7.1

Crew

7.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 09m. 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 Arajet and American Airlines, starting at $195 and $283 round-trip. Users have found that Frontier is 61% 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 $108 on Frontier. Other airlines that offer cheap prices include Arajet from $121 and United Airlines from $145 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 (79%), Qatar Airways (74%) or Frontier (64%) 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 $426, our data indicates the cheapest price to be $180. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $282.

  • 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 $139). Flying from Punta Cana to Chicago in March is currently the most expensive (average of $537). 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
Lansing
Merrillville
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
Santo Domingo 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$181Average$412FlexibilityNo cancel feeOn-time62%
ArajetCheapest$195Average$359FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$425FlexibilityNo cancel feeOn-time71%

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