PUJ - CHI

$137 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 5/2. 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 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$244
Typical prices: $396-$591
Spirit Airlines
Wed 2/11Sun 2/15
PUJ - ORD • 1 stop
Cheapest non-stop
$279
Typical prices: $305-$697
Multiple Airlines
Thu 3/12Wed 3/18
PUJ - ORD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Spirit Airlines
Cheapest • from $243 (round-trip)
Frontier
Best reviews • 5.7 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
PUJ
-
ORD
Cheapest • 58% average savings
PUJ
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 34% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 37% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
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

Wed, Feb 11 - Sun, Feb 15
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$244Spirit Airlines
Thu, Mar 12 - Wed, Mar 18
Multiple Airlines Logo
5:39 pm - 10:04 pm
PUJ
-
ORD
5h 25mnonstop
Multiple Airlines Logo
6:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$279Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$298Spirit Airlines
Thu, Feb 12 - Sat, Feb 28
Multiple Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Multiple Airlines Logo
5:05 am - 3:42 pm
ORD
-
PUJ
8h 37m
1 stop
$302Multiple Airlines
Tue, Feb 3 - Fri, Feb 6
Multiple Airlines Logo
8:05 pm - 11:15 pm
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
8:43 pm - 4:36 pm
ORD
-
PUJ
17h 53m
1 stop
$307Multiple Airlines
Tue, May 5 - Tue, May 12
Delta Logo
2:40 pm - 10:29 pm
PUJ
-
MDW
8h 49m
1 stop
Delta Logo
6:00 am - 2:48 pm
MDW
-
PUJ
7h 48m
1 stop
$369Delta
Wed, Mar 25 - Wed, Apr 1
Frontier Logo
3:32 pm - 7:47 pm
PUJ
-
MDW
29h 15m
1 stop
Frontier Logo
6:00 am - 2:15 pm
MDW
-
PUJ
7h 15m
1 stop
$406Frontier
Thu, Feb 26 - Sun, Mar 1
Frontier Logo
4:14 pm - 10:37 pm
PUJ
-
MDW
32h 23m
2 stops
Frontier Logo
6:15 am - 3:04 pm
MDW
-
PUJ
30h 49m
2 stops
$414Frontier
Wed, Mar 25 - Wed, Apr 1
Southwest Logo
1:25 pm - 10:40 pm
PUJ
-
MDW
10h 15m
1 stop
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$508Southwest
Wed, Mar 25 - Wed, Apr 1
Southwest Logo
2:35 pm - 6:40 pm
PUJ
-
MDW
5h 05mnonstop
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$533Southwest
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 absolute cheapest return flight from Punta Cana to Chicago costs $117 on the route between Punta Cana (PUJ) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Punta Cana (PUJ) and Chicago Midway Airport (MDW) were, on average, 58% cheaper than other Punta Cana-Chicago routes. The most popular route is between Punta Cana (PUJ) and Chicago O'Hare Intl Airport (ORD).

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 Monday, 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 February, where tickets cost $270 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $772 and $628 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 $318, 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 2 weeks before departure, which saves you about 34% compared to booking last minute. 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

 
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.

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier 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.

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 seasonOctober
Cheapest flight$137
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly and prices are also 18% 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 $137 for a one-way ticket and $243 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, JetBlue, 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?

    oneworld is the only airline alliance operating flights between Punta Cana and Chicago.

  • 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.

  • 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 $332 or less one-way and $236 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, +1 more

American Airlines, United Airlines, +2 more

Tuesday

American Airlines, Arajet, United Airlines, +2 more

American Airlines, Arajet, +3 more

Wednesday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Thursday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Friday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Saturday

American Airlines, Arajet, Southwest, +2 more

American Airlines, Arajet, +3 more

Sunday

American Airlines, Arajet, United Airlines, +2 more

American Airlines, Arajet, +3 more

See more direct flights

Direct returns

Chicago to Punta Cana

Monday

American Airlines, Arajet, United Airlines, +2 more

American Airlines, Arajet, +3 more

Tuesday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Wednesday

American Airlines, Arajet, United Airlines, +2 more

American Airlines, Arajet, +3 more

Thursday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Friday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

Saturday

American Airlines, Arajet, Southwest, +2 more

American Airlines, Arajet, +3 more

Sunday

American Airlines, United Airlines, Frontier, +1 more

American Airlines, United Airlines, +2 more

See more direct flights

Reviews of the top airline 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.
5.7
FrontierOverall score based on 3057 reviews
4.6Food
6.0Boarding
6.6Crew
5.5Comfort
4.3Entertainment
Airline reviews

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

10.0 ExcellentCallie, Jan 2026
PHX - ORD
Read more Frontier reviews

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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

Information on your arrival and departure airports