PUJ - CHI

$109 Find Cheap Flights from Punta Cana to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Punta Cana to Chicago departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Punta Cana to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Punta Cana to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Punta Cana to Chicago (PUJ-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Punta Cana to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Punta Cana to Chicago

Tue, Nov 25 - Tue, Dec 2
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
$216Arajet
Find Deal
Tue, Nov 25 - Sun, Nov 30
Arajet Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Arajet Logo
3:30 am - 10:15 amORD-PUJ
4h 45mnonstop
$219Arajet
Find Deal
Tue, Nov 25 - Wed, Dec 3
Multiple Airlines Logo
7:30 pm - 10:40 pmPUJ-ORD
5h 10mnonstop
Multiple Airlines Logo
5:59 pm - 12:16 pmORD-PUJ
16h 17m1 stop
$266Multiple Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 20
Spirit Airlines Logo
3:57 pm - 11:45 pmPUJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 2:49 pmORD-PUJ
8h 44m1 stop
$289Spirit Airlines
Find Deal
Thu, Oct 16 - Sat, Oct 25
Spirit Airlines Logo
3:57 pm - 11:45 pmPUJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 2:49 pmORD-PUJ
8h 44m1 stop
$290Spirit Airlines
Find Deal
Wed, Nov 26 - Tue, Dec 2
Multiple Airlines Logo
12:50 pm - 11:18 amPUJ-ORD
24h 28m1 stop
Multiple Airlines Logo
4:35 am - 11:20 amORD-PUJ
4h 45mnonstop
$295Multiple Airlines
Find Deal
Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
8:45 am - 5:25 pmORD-PUJ
6h 40m1 stop
$374United Airlines
Find Deal
Fri, Nov 21 - Thu, Nov 27
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
United Airlines Logo
3:30 pm - 5:25 pmORD-PUJ
23h 55m1 stop
$381United Airlines
Find Deal
Thu, Jan 1 - Sun, Jan 11
Frontier Logo
12:40 pm - 11:05 pmPUJ-MDW
12h 25m1 stop
Frontier Logo
6:00 am - 3:24 pmMDW-PUJ
7h 24m1 stop
$697Frontier
Find Deal
Thu, Jan 1 - Sun, Jan 11
Frontier Logo
12:40 pm - 11:05 pmPUJ-MDW
12h 25m1 stop
Frontier Logo
6:00 am - 8:15 pmMDW-PUJ
12h 15m2 stops
$760Frontier
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Choose Economy Plus on United for extra legroom.
Skip ticket counters at Punta Cana with app check-in.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Arajet
Cheapest • from $216 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
PUJ-ORD
Cheapest • 31% average savings
PUJ-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 26% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$216
Typical prices: $306-442
Arajet
Tue 11/25Tue 12/2
PUJ - ORD • Non-stop
Cheapest one-way
$109
Typical prices: $192-372
Arajet
Sat 11/15
PUJ - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Punta Cana to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Download the American Airlines app for access to inflight entertainment on your device.

Southwest

Enjoy free snacks and soft drinks; download the Southwest app for entertainment.


Use points and cash to book flights, offering flexibility if points are insufficient.

Read more about Southwestby Blane Bachelor
United Airlines

Opt for Economy Plus for up to six inches more legroom than standard economy seats.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for better connectivity.

Frontier

Purchase the Economy Bundle for a carry-on bag and seat selection included.


Avoid Basic Fare to prevent extra fees for carry-ons and seat selection.

Read more about Frontierby Stefanie Waldek
Airports
PUJ

Check in using your airline’s app to skip ticket counters and head straight to security for a smoother departure.

Read more about PUJby Mark Chesnut
ORD

Take the CTA Blue Line train from ORD to downtown Chicago for a 45-minute ride, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Chesnut

Mark Chesnut

Expert on PUJ

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more
Booking Insights

KAYAK's insights & trends for Punta Cana to Chicago flights

Get data-powered insights and trends into flights from Punta Cana to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Punta Cana to Chicago?

What is the cheapest Punta Cana to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Punta Cana to Chicago costs $230 on the route between Punta Cana (PUJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 31% cheaper than other Punta Cana-Chicago routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Punta Cana to Chicago?

The average price of all round-trip flights from Punta Cana to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Punta Cana to Chicago, look for departures on Sundays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Chicago, Monday is the cheapest day to fly and Thursday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Punta Cana to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Punta Cana to Chicago is May, where tickets cost $302 (return) on average. On the other hand, the most expensive months are June and January, where the average cost of round-trip tickets is $685 and $481 respectively.

Can I save money by flying with a layover from Punta Cana to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $419, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Punta Cana to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Punta Cana to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$109
Best time to beat the crowds but there is an average 67% increase in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Punta Cana to Chicago O'Hare Airport

When to book flights from Punta Cana to Chicago

Are your dates flexible? Find out the best times to travel from Punta Cana to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Punta Cana to Chicago

  • What is the cheapest flight from Punta Cana to Chicago?

    In the last 3 days, the lowest price for a flight from Punta Cana to Chicago was $109 for a one-way ticket and $216 for a round-trip.

  • Do I need a passport to fly between Punta Cana and Chicago?

    Yes, you’ll need a passport to travel to Chicago from Punta Cana.

  • Which airlines offer Wi-Fi service onboard planes from Punta Cana to Chicago?

    American Airlines, Air Canada, Alaska Airlines, and Delta offer inflight Wi-Fi service on the Punta Cana to Chicago flight route.

  • Which aircraft models fly most regularly from Punta Cana to Chicago?

    The Boeing 737-900 is the aircraft model that flies most regularly on the Punta Cana to Chicago flight route.

  • Which airline alliances offer flights from Punta Cana to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Punta Cana and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Punta Cana to Chicago?

    There are nonstop flights from Punta Cana to Chicago on a daily basis.

  • Which is the best airline for flights from Punta Cana to Chicago, United Airlines or Frontier?

    The two airlines most popular with KAYAK users for flights from Punta Cana to Chicago are United Airlines and Frontier. With an average price for the route of $413 and an overall rating of 7.4, United Airlines is the most popular choice. Frontier is also a great choice for the route, with an average price of $409 and an overall rating of 5.8.

  • How does KAYAK find such low prices on flights from Punta Cana to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Punta Cana to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Punta Cana to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Punta Cana is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Punta Cana to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Punta Cana with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Punta Cana to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Punta Cana up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Punta Cana to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $306 or less one-way and $320 or less round-trip.

Prefer to fly direct from Punta Cana to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Punta Cana to Chicago.
Find which airlines fly direct from Punta Cana Airport to Chicago, which days they fly and book direct flights.

Direct departures

Punta Cana to Chicago

Monday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Tuesday

American Airlines, United Airlines, Arajet, +1 more

American Airlines, United Airlines, +2 more

Wednesday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Thursday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Friday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Saturday

American Airlines, United Airlines, Arajet, +2 more

American Airlines, United Airlines, +3 more

Sunday

American Airlines, United Airlines, Arajet, +1 more

American Airlines, United Airlines, +2 more

See more direct flights

Direct returns

Chicago to Punta Cana

Monday

American Airlines, United Airlines, Arajet, +1 more

American Airlines, United Airlines, +2 more

Tuesday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Wednesday

American Airlines, United Airlines, Arajet, +1 more

American Airlines, United Airlines, +2 more

Thursday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Friday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

Saturday

American Airlines, United Airlines, Arajet, +2 more

American Airlines, United Airlines, +3 more

Sunday

American Airlines, United Airlines, Frontier

American Airlines, United Airlines, +1 more

See more direct flights

Reviews of the top airlines flying from Punta Cana to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Punta Cana to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Punta Cana to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8924 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Everything you need to know for your flight from Punta Cana to Chicago

Information on your arrival and departure airports

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