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$146+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$284
(American Airlines)

One-way from

$146
(Southwest)

Popular in

June

Cheapest in

May

Average price

$619

Good round-trip deal

$371 or less

Good one-way deal

$193 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. 13% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 7/93:31 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Wed 8/138:34 pmORD - PUJ
1 stop13h 31mAmerican Airlines
Deal found 6/10$284
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 8/54:35 pmPUJ - ORD
1 stop25h 11mUnited Airlines
Tue 8/2612:50 pmORD - PUJ
1 stop22h 50mUnited Airlines
Deal found 6/10$320
This SmartFares deal was found by Cheapflights users on 6/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/193:29 pmPUJ - ORD
1 stop19h 26mSpirit Airlines
Wed 8/275:05 amORD - PUJ
1 stop8h 29mSpirit Airlines
Deal found 6/10$343
This CheapOair deal was found by Cheapflights users on 6/11. 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 8/193:35 pmPUJ - ORD
1 stop9h 24mMultiple Airlines
Thu 8/285:10 amORD - PUJ
1 stop8h 13mMultiple Airlines
Deal found 6/11$347
This Copa Airlines deal was found by Cheapflights users on 6/10. 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.
Sat 8/22:41 pmPUJ - ORD
1 stop10h 41mCopa Airlines
Wed 8/63:07 pmORD - PUJ
1 stop18h 58mCopa Airlines
Deal found 6/10$376
This Delta deal was found by Cheapflights users on 6/11. 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 8/171:05 pmPUJ - ORD
1 stop11h 51mDelta
Sun 9/77:05 amORD - PUJ
1 stop6h 29mDelta
Deal found 6/11$380
This Booking.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/153:24 pmPUJ - MDW
1 stop20h 16mFrontier
Tue 8/511:39 amMDW - PUJ
1 stop25h 31mFrontier
Deal found 6/10$422
This Booking.com deal was found by Cheapflights users on 6/10. 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.
Wed 6/186:45 pmPUJ - ORD
2 stops39h 08mFrontier
Sat 6/216:45 amORD - PUJ
Nonstop4h 44mFrontier
Deal found 6/10$446
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 8/192:40 pmPUJ - MDW
1 stop8h 09mDelta
Wed 8/276:00 amMDW - PUJ
1 stop7h 34mDelta
Deal found 6/10$452
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 6/182:45 pmPUJ - MDW
1 stop10h 00mSouthwest
Sat 6/218:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Deal found 6/10$479
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/1012:40 pmPUJ - MDW
1 stop8h 42mMultiple Airlines
Thu 7/179:12 pmMDW - PUJ
2 stops16h 18mMultiple Airlines
Deal found 6/10$512
This CheapOair deal was found by Cheapflights users on 6/11. 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.
Thu 6/122:25 pmPUJ - ORD
1 stop18h 34mAir Canada
Mon 6/168:25 pmORD - PUJ
1 stop17h 55mAir Canada
Deal found 6/11$546

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 June 12, 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 7/9

3:31 pm-7:36 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 8/13

8:34 pm-11:05 am

1 stop13h 31m

$284

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 8/5

4:35 pm-4:46 pm

1 stop25h 11m

Chicago O'Hare Intl

Tue 8/26

12:50 pm-12:40 pm

1 stop22h 50m

$320

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 8/19

3:29 pm-9:55 am

1 stop19h 26m

Chicago O'Hare Intl

Wed 8/27

5:05 am-2:34 pm

1 stop8h 29m

$343

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 8/19

3:35 pm-11:59 pm

1 stop9h 24m

Chicago O'Hare Intl

Thu 8/28

5:10 am-2:23 pm

1 stop8h 13m

$347

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sat 8/2

2:41 pm-12:22 am

1 stop10h 41m

Chicago O'Hare Intl

Wed 8/6

3:07 pm-11:05 am

1 stop18h 58m

$376

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sun 8/17

1:05 pm-11:56 pm

1 stop11h 51m

Chicago O'Hare Intl

Sun 9/7

7:05 am-2:34 pm

1 stop6h 29m

$380

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 7/15

3:24 pm-10:40 am

1 stop20h 16m

Chicago Midway

Tue 8/5

11:39 am-2:10 pm

1 stop25h 31m

$422

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

2:40 pm-9:49 pm

1 stop8h 09m

Chicago Midway

Tue 8/26

6:00 am-1:15 pm

1 stop6h 15m

$452

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Sun 7/27

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/27

2:40 pm-2:23 pm

1 stop22h 43m

$491

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 7/10

12:40 pm-8:22 pm

1 stop8h 42m

Chicago Midway

Thu 7/17

9:12 pm-2:30 pm

2 stops16h 18m

$512

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 24 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 June 12, 2025.

It’s typically best to fly out from Punta Cana to Chicago in the morning. Doing so could potentially save you 21% 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 June 12, 2025.

The most flights from PUJ to CHI are scheduled on a Wednesday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 June 12, 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
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 American Airlines. Our recent data shows that you can find tickets from as low as $284 on this airline. Additional options worth looking into are United Airlines and Spirit Airlines, starting at $320 and $343 round-trip. Users have found that American Airlines is 30% 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 $146 on Southwest. Other airlines that offer cheap prices include American Airlines from $146 and United Airlines from $152 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 (88%), Frontier (80%) or United Airlines (70%) 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 $348, our data indicates the cheapest price to be $123. The most popular route (Punta Cana - Chicago O'Hare Intl), is priced around $312.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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.
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Santiago de los Caballeros 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$387FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$426FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$402Average$556FlexibilityNo cancel feeOn-time71%

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