PUJ - CHI

$110 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 12/9. 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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Everything you should know

Cheapest round-trip
$184
Overall average: $342
Frontier
Fri 12/5Fri 12/12
PUJ - ORD • Non-stop
Cheapest one-way
$110
Typical prices: $230-$335
Frontier
Tue 12/9
PUJ - ORD • Non-stop
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
Frontier
Cheapest • from $184 (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 • 59% average savings
PUJ-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 30% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
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

Fri, Dec 5 - Fri, Dec 12
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$184Frontier
Find Deal
Fri, Dec 5 - Fri, Dec 12
Frontier Logo
6:50 pm - 10:00 pmPUJ-ORD
5h 10mnonstop
Frontier Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$193Frontier
Find Deal
Tue, Jan 13 - Tue, Jan 20
Frontier Logo
6:49 pm - 10:11 pmPUJ-ORD
5h 22mnonstop
Frontier Logo
7:00 am - 1:37 pmORD-PUJ
4h 37mnonstop
$203Frontier
Find Deal
Sat, Jan 31 - Sat, Feb 7
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$240Arajet
Find Deal
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 1:37 pmORD-PUJ
4h 37mnonstop
$241Multiple Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Arajet Logo
5:47 am - 8:57 amPUJ-ORD
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD-PUJ
4h 45mnonstop
$243Arajet
Find Deal
Fri, Dec 5 - Fri, Dec 12
Multiple Airlines Logo
6:08 pm - 12:19 amPUJ-ORD
8h 11m1 stop
Multiple Airlines Logo
7:10 am - 1:47 pmORD-PUJ
4h 37mnonstop
$244Multiple Airlines
Find Deal
Mon, Nov 3 - Mon, Nov 10
Spirit Airlines Logo
4:25 pm - 12:27 amPUJ-ORD
10h 02m1 stop
Spirit Airlines Logo
5:10 am - 3:20 pmORD-PUJ
8h 10m1 stop
$291Spirit Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Spirit Airlines Logo
12:52 pm - 8:17 pmPUJ-ORD
8h 25m1 stop
Spirit Airlines Logo
5:10 am - 3:20 pmORD-PUJ
8h 10m1 stop
$298Spirit Airlines
Find Deal
Fri, Dec 5 - Fri, Dec 12
American Airlines Logo
2:29 pm - 5:47 pmPUJ-ORD
5h 18mnonstop
American Airlines Logo
9:46 am - 4:27 pmORD-PUJ
4h 41mnonstop
$307American Airlines
Find Deal
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.

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 $112 on the route between Punta Cana (PUJ) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 59% 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 Fridays 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 $299 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $685 and $511 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 $381, 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.

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

Good to know

Low seasonOctober
Cheapest flight$110
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 19% 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 $110 for a one-way ticket and $184 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 MAX 8 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Punta Cana and Chicago, with Star Alliance 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 $443 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 $353 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 $203 or less one-way and $195 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, United Airlines

American Airlines, Frontier, +1 more

Tuesday

American Airlines, Arajet, Frontier, +1 more

American Airlines, Arajet, +2 more

Wednesday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Thursday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Friday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Saturday

American Airlines, Arajet, Frontier, +2 more

American Airlines, Arajet, +3 more

Sunday

American Airlines, Arajet, Frontier, +1 more

American Airlines, Arajet, +2 more

See more direct flights

Direct returns

Chicago to Punta Cana

Monday

American Airlines, Arajet, Frontier, +1 more

American Airlines, Arajet, +2 more

Tuesday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Wednesday

American Airlines, Arajet, Frontier, +1 more

American Airlines, Arajet, +2 more

Thursday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Friday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +1 more

Saturday

American Airlines, Arajet, Frontier, +2 more

American Airlines, Arajet, +3 more

Sunday

American Airlines, Frontier, United Airlines

American Airlines, Frontier, +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 8988 reviews
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
6.6Food
Airline reviews

Excellent all round, first time flying United. App is very helpful.

10.0 ExcellentBrad, Oct 2025SJD - ORD
Read more United Airlines reviews

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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

Information on your arrival and departure airports

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