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Punta Cana

$135+ Cheap flights from Chicago (CHI) to Punta Cana (PUJ)

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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Jul 23 — Jul 301
Thu 7/23
Thu 7/30
1 adult, Economy
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Find cheap flights from Chicago to Punta Cana with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Punta Cana are usually found in September or August, booked 48 days in advance, depart on a Monday or Saturday and return on a Friday

Cheap flight deals from Chicago to Punta Cana

Cheapest flights from Chicago to Punta Cana
Explore the most affordable flight options available from Chicago to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2026.

This Arajet deal was found by Cheapflights users on 6/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Sun 9/206:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Deal found 6/22$422
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/2212:12 pm
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Sat 8/2911:39 am
PUJ
-
ORD
1 stop12h 48m
Multiple Airlines
Deal found 6/22$429
This American Airlines deal was found by Cheapflights users on 6/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:00 pm
ORD
-
PUJ
1 stop16h 55m
American Airlines
Thu 7/23:01 pm
PUJ
-
ORD
Nonstop5h 26m
American Airlines
Deal found 6/22$430
This Mytrip deal was found by Cheapflights users on 6/22. 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.
Sat 8/1512:12 pm
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Sat 8/223:37 pm
PUJ
-
ORD
1 stop17h 16m
Multiple Airlines
Deal found 6/22$431
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:30 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Thu 7/307:30 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Deal found 6/19$432
This Frontier deal was found by Cheapflights users on 6/22. 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.
Mon 8/312:44 am
ORD
-
PUJ
1 stop8h 56m
Frontier
Tue 8/119:29 pm
PUJ
-
ORD
2 stops15h 46m
Frontier
Deal found 6/22$433
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 8/1512:12 pm
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Wed 9/21:29 pm
PUJ
-
ORD
1 stop10h 58m
Multiple Airlines
Deal found 6/20$434
This CheapOair deal was found by Cheapflights users on 6/23. 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.
Fri 10/236:45 am
ORD
-
PUJ
Nonstop4h 45m
Multiple Airlines
Fri 10/303:30 pm
PUJ
-
ORD
1 stop9h 14m
Multiple Airlines
Deal found 6/23$435
This Cheapflightsfares deal was found by Cheapflights users on 6/20. 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.
Tue 9/17:00 am
ORD
-
PUJ
1 stop7h 27m
JetBlue
Tue 9/84:41 pm
PUJ
-
ORD
1 stop8h 03m
JetBlue
Deal found 6/20$436
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:44 pm
ORD
-
PUJ
2 stops20h 21m
Multiple Airlines
Sat 9/127:02 am
PUJ
-
ORD
Nonstop5h 10m
Multiple Airlines
Deal found 6/19$437
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/512:12 pm
ORD
-
PUJ
Nonstop4h 45m
Arajet
Sun 9/136:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Deal found 6/20$438
This Arajet deal was found by Cheapflights users on 6/20. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:30 am
ORD
-
PUJ
Nonstop4h 45m
Arajet
Sun 9/136:00 pm
PUJ
-
ORD
Nonstop5h 10m
Arajet
Deal found 6/20$439

Find flight deals from Chicago to Punta Cana

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Punta Cana (PUJ). 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 June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$422
(Arajet)

One-way from

$135
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$661

Good round-trip deal

$531 or less

Good one-way deal

$264 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
Search Deals
From Chicago (CHI) to Punta Cana
Search Deals
One-way flight from Chicago (CHI) to Punta Cana
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Punta Cana.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Punta Cana.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Punta Cana 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 June 23, 2026.
Use the filters below to find and compare flights from Chicago to Punta Cana that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 8/21

6:42 pm-12:59 pm

1 stop17h 17m

Punta Cana

Wed 9/2

2:50 pm-9:17 am

2 stops19h 27m

$491

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 8/21

7:30 pm-12:59 pm

1 stop16h 29m

Punta Cana

Thu 8/27

2:50 pm-7:56 am

2 stops18h 06m

$491

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 8/20

7:00 am-3:27 pm

1 stop7h 27m

Punta Cana

Wed 9/2

4:41 pm-11:44 pm

1 stop8h 03m

$503

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 9/13

6:00 am-1:52 pm

1 stop6h 52m

Punta Cana

Thu 9/17

3:20 pm-11:31 pm

1 stop9h 11m

$503

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 8/20

6:42 pm-2:39 pm

2 stops18h 57m

Punta Cana

Tue 9/1

4:04 pm-10:36 pm

1 stop7h 32m

$505

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 8/20

7:30 pm-2:39 pm

2 stops18h 09m

Punta Cana

Thu 8/27

4:04 pm-8:44 am

1 stop17h 40m

$505

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 9/16

5:00 am-3:30 pm

1 stop9h 30m

Punta Cana

Wed 9/23

1:50 pm-12:28 am

1 stop11h 38m

$508
Quickest round-trip

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 7/3

6:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sat 7/11

7:02 am-11:12 am

Nonstop5h 10m

$521

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 10/13

5:00 am-3:30 pm

1 stop9h 30m

Punta Cana

Tue 10/20

3:35 pm-11:32 pm

1 stop8h 57m

$530

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 9/2

6:15 am-1:20 pm

1 stop6h 05m

Punta Cana

Fri 9/11

1:45 pm-7:35 am

2 stops18h 50m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 45 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Punta Cana

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 Chicago to Punta Cana in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
GotogatePrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 Chicago-Punta Cana flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Punta Cana flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Punta Cana flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Punta Cana 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 Chicago-Punta Cana 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 Chicago to Punta Cana

Have a flexible travel schedule? Discover the best time to fly to Punta Cana from Chicago 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 Chicago to Punta Cana

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $110). Flying from Chicago to Punta Cana in July is currently the most expensive (average of $1,151). 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 CHI to PUJ?

Find hourly flight availability from Chicago to Punta Cana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 23, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Punta Cana as you normally would.

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

How often are flights from Chicago to Punta Cana delayed?

About 20% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 138 minutes.

What is the most punctual flight time for Chicago to Punta Cana flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Punta Cana flights?

Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.

How far ahead should I book a flight from Chicago to Punta Cana?

To ensure you get the cheapest price possible for a flight from Chicago to Punta Cana, you should look to book at least 17 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

The best insider tips for Chicago to Punta Cana 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 Chicago to Punta Cana 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 Punta Cana

Get insights into the airlines that provide service to Punta Cana. 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 Punta Cana. Reviews last updated June 23, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Punta Cana by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,242 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,879 reviews
Southwest
7.9
Good
4,242 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,748 reviews
Southwest
7.9
Good
4,242 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,869 reviews
Southwest
7.9
Good
4,242 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Chicago to Punta Cana. 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 into for flights to Punta Cana from Chicago?

    If you book a flight to Punta Cana from Chicago, you will be flying to Punta Cana, which is the city’s only airport. Punta Cana (PUJ) is located 9.2 mi from the center of Punta Cana. There are 2 flights from Chicago to Punta Cana per day from 10 different airlines.

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

    Airlines like Delta, JetBlue, and United Airlines fly from Chicago to Punta Cana in about 7h 27m. The time it takes to get you to your destination can typically vary by up to 9h 50m. The distance from Chicago to Punta Cana is about 1982 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on WorldTicket is currently your cheapest option to Punta Cana, with prices starting at $173. Additional round-trip tickets that might be worth considering are offered by Arajet and Frontier, with the lowest prices starting at $216 and $225, respectively. WorldTicket is 66% cheaper than the average price of flights available within the next 90 days to this destination.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $87. Users have also found prices from $100 and $161 on Arajet and United Airlines, respectively.

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

    Before booking your flight to Punta Cana from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (87%), American Airlines (82%), Arajet( 79%).

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

    Looking for the cheapest flight from Chicago to Punta Cana? While on average our users pay $749, our data indicates the cheapest price to be $148. The most popular route (Chicago O'Hare Intl - Punta Cana), is priced around $285.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Punta Cana 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 Chicago to Punta Cana?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $110). Flying from Chicago to Punta Cana in July is currently the most expensive (average of $1,151). 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 Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Bavaro

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Top 9 airlines flying from Chicago to Punta Cana

Discover the top 9 airlines that operate flights from Chicago to Punta Cana. 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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
ArajetCheapest$216Average$360FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$225Average$702FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$226Average$517FlexibilityNo cancel feeOn-time67%
Hahn AirCheapest$228Average$484FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$245Average$250FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$260Average$434FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$348Average$661FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$365Average$579FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$503Average$816FlexibilityNo cancel feeOn-time63%

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