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Punta Cana

$106+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Punta Cana are usually found in July or January, booked 46 days in advance, depart on a Tuesday or Monday and return on a Saturday

Cheap 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 July 28, 2025.

Round-trip from

$298
(FlightHub)

One-way from

$106
(Cheapflightsfares)

Popular in

March

Cheapest in

July

Average price

$482

Good round-trip deal

$260 or less

Good one-way deal

$146 or less
From Chicago (CHI) to Punta Cana
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One-way flight from Chicago (CHI) to Punta Cana
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Highest demand for flights based on searches. 3% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Punta Cana.
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Price to beat on a one-way flight from Chicago (CHI) to Punta Cana.
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Find 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 July 28, 2025.

This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Sat 9/133:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Deal found 7/27$298
This Frontier deal was found by Cheapflights users on 7/27. 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.
Tue 7/296:45 amORD - PUJ
Nonstop4h 40mFrontier
Wed 8/65:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 7/27$301
This CheapOair deal was found by Cheapflights users on 7/27. 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.
Tue 8/126:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Tue 8/1912:40 pmPUJ - ORD
1 stop10h 42mMultiple Airlines
Deal found 7/27$308
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sat 8/237:05 pmORD - PUJ
1 stop16h 45mAmerican Airlines
Wed 8/273:30 pmPUJ - ORD
Nonstop5h 00mAmerican Airlines
Deal found 7/26$333
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 11/96:00 amORD - PUJ
1 stop7h 20mDelta
Fri 11/142:03 pmPUJ - ORD
1 stop9h 09mDelta
Deal found 7/28$343
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 11/106:00 amMDW - PUJ
1 stop6h 23mDelta
Fri 11/143:50 pmPUJ - MDW
1 stop7h 54mDelta
Deal found 7/27$343
This Booking.com deal was found by Cheapflights users on 7/25. 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 8/99:12 pmMDW - PUJ
2 stops43h 03mFrontier
Tue 8/123:25 pmPUJ - MDW
1 stop20h 15mFrontier
Deal found 7/25$356
This Southwest deal was found by Cheapflights users on 7/27. 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.
Fri 10/35:00 amMDW - PUJ
1 stop8h 30mSouthwest
Wed 10/81:40 pmPUJ - MDW
1 stop9h 55mSouthwest
Deal found 7/27$368
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/2010:51 amMDW - PUJ
1 stop23h 50mMultiple Airlines
Sat 9/2712:36 pmPUJ - MDW
1 stop21h 42mMultiple Airlines
Deal found 7/27$437

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 July 28, 2025.
Use the filters below to find and compare flights from Chicago to Punta Cana that are best for you.

Fly from

Chicago

Fly to

Punta Cana

Route

Depart

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Sat 9/13

3:19 pm-10:48 pm

1 stop8h 29m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 8/10

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Sat 8/23

12:31 pm-11:59 pm

2 stops12h 28m

$302

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/9

6:45 am-12:25 pm

Nonstop4h 40m

Punta Cana

Wed 8/13

5:08 pm-9:16 pm

Nonstop5h 08m

$309

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/23

7:05 pm-12:50 pm

1 stop16h 45m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$333

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/22

6:00 am-2:32 pm

1 stop7h 32m

Punta Cana

Thu 9/25

2:45 pm-9:36 pm

1 stop7h 51m

$343

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 9/23

3:45 pm-12:32 pm

2 stops19h 47m

Punta Cana

Fri 9/26

1:57 pm-4:31 pm

2 stops27h 34m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/9

9:12 pm-5:15 pm

2 stops43h 03m

Punta Cana

Tue 8/12

3:25 pm-10:40 am

1 stop20h 15m

$356

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/3

5:00 am-2:30 pm

1 stop8h 30m

Punta Cana

Wed 10/8

1:40 pm-10:35 pm

1 stop9h 55m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 9/20

10:51 am-11:41 am

1 stop23h 50m

Punta Cana

Sat 9/27

12:36 pm-9:18 am

1 stop21h 42m

$437

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 8/10

6:45 am-12:25 pm

Nonstop4h 40m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 18 results
1
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The best insider tips for Chicago to Punta Cana 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 Chicago to Punta Cana trip
Airports
ORD

For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
PUJ

At PUJ, immigration is swift, often under 20 minutes, making arrivals efficient.

Read more about PUJby Matt Meltzer
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 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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Punta Cana. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Punta Cana, you should look to book at least 46 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.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $443). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $594). 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 July 28, 2025.

One of the essential ways to save on airfare from Chicago to Punta Cana is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 39% on airfare.

What is the cheapest day to fly from Chicago to Punta Cana?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Punta Cana. Price data was last updated on July 20, 2025.

Travelers seeking maximum savings on their Chicago to Punta Cana flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Punta Cana

Explore weekly flight availability from Chicago to Punta Cana. 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 July 28, 2025.

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

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

What’s the top layover airport for flights from Chicago to Punta Cana?

Share of 1-stop round-trip flights from Chicago to Punta Cana chosen by Cheapflights users in the past 12 months, using the same layover each way.

Panama City (PTY) – chosen by Cheapflights users on 38% of 1-stop itineraries from Chicago to Punta Cana on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Punta Cana?

Average round-trip fare for 1-stop flights from Chicago to Punta Cana, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $231.

What’s the fastest layover option from Chicago to Punta Cana?

Shortest average travel time for 1-stop one-way flights from Chicago to Punta Cana, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 3h 38m.

Which airport typically offers the quickest layover for flights from Chicago to Punta Cana?

Average layover duration for 1-stop one-way flights from Chicago to Punta Cana, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.

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 July 28, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Copa 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
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 4 flights from Chicago to Punta Cana per day from 9 different airlines.

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

    Flying on Spirit Airlines is currently your cheapest option to Punta Cana, with prices starting at $298. Additional round-trip tickets that might be worth considering are offered by Frontier and American Airlines, with the lowest prices starting at $309 and $333, respectively. Spirit Airlines is 44% 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 $106. Users have also found prices from $113 and $155 on Spirit Airlines 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 (85%), American Airlines (77%), Frontier( 69%).

  • 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 $384, our data indicates the cheapest price to be $147. The most popular route (Chicago O'Hare Intl - Punta Cana), is priced around $274.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $443). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $594). 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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$223Average$434FlexibilityNo cancel feeOn-time62%
ArajetCheapest$235Average$315FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$270Average$361FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$335Average$861FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$342Average$632FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$362Average$596FlexibilityNo cancel feeOn-time71%
DeltaCheapest$386Average$724FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%
AviancaCheapest$615Average$1,422FlexibilityNo cancel feeOn-time71%

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