CHI - PUJ

$136 Find Cheap Flights from Chicago to Punta Cana

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Punta Cana departing on 5/4. 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, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana.
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Everything you should know

Cheapest round-trip
$304
Typical prices: $637-$331
Spirit Airlines
จ. 5/4ศ. 5/8
ORD - PUJ • 1 stop
Cheapest non-stop
$311
Typical prices: $628-$391
Arajet
ส. 6/27ส. 7/4
ORD - PUJ • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Frontier's Premium Bundle offers extra legroom.
Complete your E-Ticket form online for Punta Cana.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $304 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and others. Average duration is 4h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 30% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 83% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $277 (round-trip)
Shortest trip • 6h 28m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 8% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 21% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
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+1
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We hope you love your trip to Punta Cana!
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Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Punta Cana 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 Chicago to Punta Cana

จ., พ.ค. 4 - ศ., พ.ค. 8
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
Spirit Airlines Logo
2:40 pm - 11:15 pm
PUJ
-
ORD
9h 35m
1 stop
$304Spirit Airlines
ศ., พ.ค. 8 - อ., พ.ค. 12
Frontier Logo
5:30 pm - 9:18 am
ORD
-
PUJ
14h 48m
1 stop
Frontier Logo
9:29 pm - 11:13 pm
PUJ
-
ORD
26h 44m
2 stops
$305Frontier
จ., พ.ค. 11 - พฤ., พ.ค. 14
Frontier Logo
4:52 pm - 8:19 pm
MDW
-
PUJ
50h 27m
2 stops
Frontier Logo
3:27 pm - 11:09 am
PUJ
-
MDW
20h 42m
2 stops
$305Frontier
ศ., พ.ค. 1 - ส., พ.ค. 9
Frontier Logo
1:45 pm - 1:54 pm
ORD
-
PUJ
23h 09m
2 stops
Frontier Logo
3:35 pm - 7:55 am
PUJ
-
ORD
17h 20m
1 stop
$306Frontier
ส., พ.ค. 2 - พฤ., พ.ค. 7
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
9:29 pm - 11:04 am
PUJ
-
MDW
38h 35m
2 stops
$306Frontier
จ., เม.ย. 27 - พฤ., เม.ย. 30
Spirit Airlines Logo
5:05 am - 2:49 pm
ORD
-
PUJ
8h 44m
1 stop
Spirit Airlines Logo
3:54 pm - 12:24 am
PUJ
-
ORD
9h 30m
1 stop
$307Spirit Airlines
ส., พ.ค. 9 - พ., พ.ค. 13
Frontier Logo
7:52 pm - 10:57 am
ORD
-
PUJ
14h 05m
1 stop
Frontier Logo
9:29 pm - 7:55 am
PUJ
-
ORD
35h 26m
2 stops
$308Frontier
จ., เม.ย. 27 - พฤ., เม.ย. 30
Multiple Airlines Logo
4:30 am - 10:15 am
ORD
-
PUJ
4h 45mnonstop
Multiple Airlines Logo
3:54 pm - 12:24 am
PUJ
-
ORD
9h 30m
1 stop
$309Multiple Airlines
ส., พ.ค. 2 - พฤ., พ.ค. 7
Frontier Logo
5:50 am - 1:54 pm
ORD
-
PUJ
7h 04m
1 stop
Frontier Logo
9:29 pm - 7:55 am
PUJ
-
ORD
35h 26m
2 stops
$310Frontier
อา., พ.ค. 3 - พฤ., พ.ค. 7
Spirit Airlines Logo
5:05 am - 2:49 pm
ORD
-
PUJ
8h 44m
1 stop
Spirit Airlines Logo
2:40 pm - 11:15 pm
PUJ
-
ORD
9h 35m
1 stop
$311Spirit Airlines
Booking Insights

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

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Punta Cana departing in May.

What is the cheapest Chicago to Punta Cana flight route?

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

The cheapest return flight from Chicago to Punta Cana costs $282 on the route between Chicago O'Hare Intl Airport (ORD) and Punta Cana (PUJ). Over the past month, this route was, on average, 30% cheaper than other Chicago-Punta Cana routes. It is also the most popular route.

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

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

When flying from Chicago to Punta Cana, you should consider leaving on a Monday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Punta Cana, 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 Chicago to Punta Cana is September, where tickets cost $395 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $601 and $580 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $599 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Punta Cana, 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 Chicago to Punta Cana, you should book around 2 weeks before departure, which saves you about 8% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Punta Cana

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines and ORD

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Mark Chesnut

Mark Chesnut

Expert on PUJ

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.

Good to know

Low seasonSeptember
Cheapest flight$136
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago O'Hare Airport to Punta Cana

When to book flights from Chicago to Punta Cana

Are your dates flexible? Find out the best times to travel from Chicago to Punta Cana 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 Chicago to Punta Cana

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

    In the last 3 days, the lowest price for a flight from Chicago to Punta Cana was $136 for a one-way ticket and $304 for a round-trip.

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

    Yes

  • Which airports will I be using when flying from Chicago to Punta Cana?

    Chicago is served by 2 major airports and there is only 1 main airport in Punta Cana. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Punta Cana.

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago to Punta Cana flight route.

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

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

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

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

  • Which is the best airline for flights from Chicago to Punta Cana, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Punta Cana are Southwest and Delta. With an average price for the route of $608 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $485 and an overall rating of 7.9.

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

    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 Chicago to Punta Cana.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Punta Cana from Chicago 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 Chicago to Punta Cana?

    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 Punta Cana with an airline and back to Chicago with another airline.

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

    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 Punta Cana from Chicago 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 Chicago to Punta Cana

  • Looking for a cheap flight? 25% of our users found flights on this route for $260 or less one-way and $559 or less round-trip.

Prefer to fly direct from Chicago to Punta Cana?

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

Direct departures

Chicago to Punta Cana

Monday

American Airlines,Arajet,United Airlines, +1 more

American Airlines,Arajet, +2 more

Tuesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,Arajet, +1 more

American Airlines,United Airlines, +2 more

Saturday

American Airlines,Arajet,Southwest, +1 more

American Airlines,Arajet, +2 more

Sunday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Punta Cana to Chicago

Monday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Arajet, +1 more

American Airlines,United Airlines, +2 more

Friday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Saturday

American Airlines,Arajet,Southwest, +1 more

American Airlines,Arajet, +2 more

Sunday

American Airlines,Arajet,United Airlines, +1 more

American Airlines,Arajet, +2 more

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Punta Cana

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Punta Cana. 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 Chicago to Punta Cana? 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.
8.0
SouthwestOverall score based on 4328 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Great flight. I didn't get a drink because I was asleep whole on the flight.

10.0 ExcellentPaul, Apr 2026
PHX - MDW
Read more Southwest reviews

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

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

Information on your arrival and departure airports