PUJ - CHI

$128 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 11/22. 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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Flights 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

Wed, Jul 9 - Wed, Aug 13
American Airlines Logo
3:31 pm - 7:36 pmPUJ-ORD
5h 05mnonstop
American Airlines Logo
8:34 pm - 11:05 amORD-PUJ
13h 31m1 stop
$284American Airlines
Find Deal
Wed, Jul 9 - Wed, Aug 13
American Airlines Logo
3:31 pm - 7:36 pmPUJ-ORD
5h 05mnonstop
American Airlines Logo
5:54 pm - 3:50 pmORD-PUJ
20h 56m1 stop
$291American Airlines
Find Deal
Wed, Jul 9 - Thu, Aug 21
United Airlines Logo
1:50 pm - 5:55 pmPUJ-ORD
5h 05mnonstop
United Airlines Logo
9:31 pm - 12:40 pmORD-PUJ
14h 09m1 stop
$296United Airlines
Find Deal
Thu, Jul 3 - Wed, Jul 16
United Airlines Logo
4:35 pm - 4:52 pmPUJ-ORD
25h 17m1 stop
United Airlines Logo
9:23 am - 3:05 pmORD-PUJ
4h 42mnonstop
$302United Airlines
Find Deal
Thu, Jul 10 - Tue, Jul 22
Spirit Airlines Logo
3:25 pm - 11:53 pmPUJ-ORD
9h 28m1 stop
Spirit Airlines Logo
5:05 am - 2:30 pmORD-PUJ
8h 25m1 stop
$310Spirit Airlines
Find Deal
Wed, Jul 30 - Wed, Aug 6
Spirit Airlines Logo
3:25 pm - 11:13 pmPUJ-ORD
8h 48m1 stop
Spirit Airlines Logo
5:05 am - 2:30 pmORD-PUJ
8h 25m1 stop
$324Spirit Airlines
Find Deal
Tue, Jul 29 - Fri, Aug 8
Southwest Logo
3:45 pm - 7:35 pmPUJ-MDW
4h 50mnonstop
Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
$332Southwest
Find Deal
Tue, Jul 29 - Fri, Aug 8
Frontier Logo
3:24 pm - 10:40 amPUJ-MDW
20h 16m1 stop
Frontier Logo
6:40 pm - 10:55 amMDW-PUJ
15h 15m1 stop
$424Frontier
Find Deal
Wed, Jul 2 - Sun, Aug 3
Southwest Logo
4:05 pm - 7:55 pmPUJ-MDW
4h 50mnonstop
Southwest Logo
8:10 am - 1:45 pmMDW-PUJ
4h 35mnonstop
$427Southwest
Find Deal
Thu, Jul 3 - Sat, Aug 9
Frontier Logo
10:17 am - 10:32 pmPUJ-MDW
13h 15m1 stop
Frontier Logo
9:12 pm - 8:54 amMDW-PUJ
10h 42m1 stop
$436Frontier
Find Deal
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
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
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.

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
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
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
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
Useful Info

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.

What is the cheapest Punta Cana to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Punta Cana to Chicago.

Our data shows that the cheapest route for a return flight from Punta Cana to Chicago cost $315 and was between Punta Cana (PUJ) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from Punta Cana (PUJ) to Chicago Midway Airport (MDW). The average price for a return flight for this route is $315.

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 Saturdays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago, Tuesday 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 $619 and $497 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 $432, 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$128
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 14% 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 $128 for a one-way ticket and $284 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, Delta, Alaska Airlines, and Air Canada 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Punta Cana to Chicago are United Airlines and American Airlines. With an average price for the route of $413 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $542 and an overall rating of 7.2.

  • 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 $320 or less one-way and $387 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, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Tuesday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Wednesday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Thursday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Friday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Saturday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Sunday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

See more direct flights

Direct returns

Chicago to Punta Cana

Monday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Tuesday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Wednesday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Thursday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Friday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Saturday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

Sunday

American Airlines, Frontier, Southwest, +1 more

American Airlines, Frontier, +2 more

See more direct flights

Top 3 airlines serving 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 8801 reviews
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
7.0Entertainment
Airline reviews

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.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

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.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

You ant watch TV if you don't have a device, the seats have more space, and the snacks are different.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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

Information on your arrival and departure airports

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