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$149+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$263
(United Airlines)

One-way from

$149
(United Airlines)

Popular in

June

Cheapest in

May

Average price

$356

Good round-trip deal

$269 or less

Good one-way deal

$251 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
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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. 11% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This eDestinos deal was found by Cheapflights users on 4/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/812:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
Sun 5/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 4/27$288
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/83:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Sun 5/118:05 amORD - PUJ
Nonstop4h 30mAmerican Airlines
Deal found 4/28$318
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/261:32 pmPUJ - ORD
2 stops10h 56mFrontier
Fri 6/276:45 amORD - PUJ
Nonstop4h 44mFrontier
Deal found 4/28$321
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/11:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Mon 5/59:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/28$340
This Delta deal was found by Cheapflights users on 4/28. 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.
Thu 5/82:47 pmPUJ - MDW
1 stop7h 41mDelta
Sun 5/116:00 amMDW - PUJ
1 stop7h 45mDelta
Deal found 4/28$341
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 7/92:52 pmPUJ - ORD
1 stop7h 38mDelta
Wed 8/67:00 amORD - PUJ
1 stop6h 51mDelta
Deal found 4/28$341
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:22 pmPUJ - ORD
1 stop18h 28mMultiple Airlines
Sun 6/151:43 pmORD - PUJ
1 stop29h 11mMultiple Airlines
Deal found 4/28$390
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2610:06 amPUJ - MDW
1 stop11h 11mFrontier
Sat 6/289:12 pmMDW - PUJ
1 stop10h 39mFrontier
Deal found 4/28$402
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2610:06 amPUJ - MDW
1 stop11h 11mMultiple Airlines
Fri 6/279:40 amMDW - PUJ
1 stop13h 02mMultiple Airlines
Deal found 4/28$419
This Copa Airlines deal was found by Cheapflights users on 4/27. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/112:03 pmPUJ - ORD
1 stop13h 17mCopa Airlines
Wed 7/93:07 pmORD - PUJ
1 stop19h 32mCopa Airlines
Deal found 4/27$433
This Southwest deal was found by Cheapflights users on 4/27. 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.
Tue 7/14:05 pmPUJ - MDW
Nonstop4h 50mSouthwest
Wed 7/99:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Deal found 4/27$508
This deal was found by Cheapflights users on 4/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/172:55 pmPUJ - ORD
1 stop9h 30mJetBlue
Thu 6/196:15 amORD - PUJ
1 stop11h 06mJetBlue
Deal found 4/27$537

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 29, 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

Fri 7/4

1:50 pm-5:55 pm

Nonstop5h 05m

Chicago O'Hare Intl

Mon 7/14

9:23 am-3:05 pm

Nonstop4h 42m

$263

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 6/26

1:32 pm-11:28 pm

2 stops10h 56m

Chicago O'Hare Intl

Fri 6/27

6:45 am-12:29 pm

Nonstop4h 44m

$321

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 7/10

4:10 pm-1:29 pm

2 stops22h 19m

Chicago O'Hare Intl

Sun 7/20

5:49 pm-3:50 pm

2 stops21h 01m

$328

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/28

3:22 pm-11:04 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 6/25

5:05 am-2:10 pm

1 stop8h 05m

$331

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/8

2:47 pm-9:28 pm

1 stop7h 41m

Chicago Midway

Sun 5/11

6:00 am-2:45 pm

1 stop7h 45m

$341

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

2:52 pm-9:30 pm

1 stop7h 38m

Chicago O'Hare Intl

Wed 8/6

7:00 am-2:51 pm

1 stop6h 51m

$341

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Fri 6/6

3:22 pm-8:50 am

1 stop18h 28m

Chicago O'Hare Intl

Sun 6/15

1:43 pm-7:54 pm

1 stop29h 11m

$390

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/26

10:06 am-8:17 pm

1 stop11h 11m

Chicago Midway

Sat 6/28

9:12 pm-8:51 am

1 stop10h 39m

$402

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/26

10:06 am-8:17 pm

1 stop11h 11m

Chicago Midway

Fri 6/27

9:40 am-11:42 pm

1 stop13h 02m

$419

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 7/1

1:56 pm-11:52 pm

1 stop10h 56m

Chicago O'Hare Intl

Thu 7/31

3:07 pm-11:39 am

1 stop19h 32m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 30 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Punta Cana-Chicago flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

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. Consider the VIP Premium Departure Service for a faster, more comfortable experience.

Read more about PUJby Matt Meltzer
ORD

After arriving at ORD, consider taking the “L” train for a reliable trip to downtown Chicago, avoiding potential traffic delays.

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 April 29, 2025.

It’s typically best to fly out from Punta Cana to Chicago in the morning. Doing so could potentially save you 23% 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 April 29, 2025.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 29, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Punta Cana to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,410 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,697 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,292 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    Our cheapest airline available from Punta Cana to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $263 on this airline. Additional options worth looking into are Frontier and American Airlines, starting at $321 and $328 round-trip. Users have found that United Airlines is 37% 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 $149 on United Airlines. Other airlines that offer cheap prices include American Airlines from $157 and Spirit Airlines from $161 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 Frontier (69%), American Airlines (58%) or United Airlines (51%) 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 $406, our data indicates the cheapest price to be $131. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $263.

  • 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 Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.
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Punta Cana to O'Hare Intl flights
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Punta Cana 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$379FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$426FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$405Average$599FlexibilityNo cancel feeOn-time71%

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