MDW - PUJ

$173 Find Cheap Flights from Chicago Midway Airport to Punta Cana - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Punta Cana departing on 8/25. 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

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Everything you should know

Cheapest round-trip
$380
Typical prices: $721-$928
Southwest
Mon 8/31Thu 9/3
MDW - PUJ • 1 stop
Cheapest non-stop
$1,400
Southwest
Sat 11/21Sat 11/28
MDW - PUJ • Non-stop
Nonstop flights
Mon, Thu, Fri, Sun
You can fly direct with Southwest. Average duration is 0
Direct flights
Direct flights
+1
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Direct flights
Direct flights
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Top airlines
Cheapest • from $380 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Avoid delays
Most punctual • 69% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Punta Cana!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Punta Cana (MDW-PUJ)

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

Mon, Aug 31 - Thu, Sep 3
Southwest Logo
5:00 am - 1:40 pm
MDW
-
PUJ
7h 40m
1 stop
Southwest Logo
1:45 pm - 10:45 pm
PUJ
-
MDW
10h 00m
1 stop
$380Southwest
Sat, Sep 26 - Fri, Oct 2
Delta Logo
9:59 am - 12:42 pm
MDW
-
PUJ
25h 43m
2 stops
Delta Logo
2:08 pm - 10:36 am
PUJ
-
MDW
21h 28m
2 stops
$385Delta
Sat, Sep 26 - Thu, Oct 1
Delta Logo
4:30 pm - 12:42 pm
MDW
-
PUJ
19h 12m
2 stops
Delta Logo
4:00 pm - 9:07 am
PUJ
-
MDW
18h 07m
2 stops
$385Delta
Sat, Aug 22 - Wed, Aug 26
Delta Logo
9:24 am - 11:43 am
MDW
-
PUJ
25h 19m
2 stops
Delta Logo
2:50 pm - 9:17 am
PUJ
-
MDW
19h 27m
2 stops
$385Delta
Sun, Sep 13 - Thu, Sep 17
Southwest Logo
5:00 am - 1:55 pm
MDW
-
PUJ
7h 55m
1 stop
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
$427Southwest
Sun, Sep 13 - Thu, Sep 17
Southwest Logo
5:00 am - 1:55 pm
MDW
-
PUJ
7h 55m
1 stop
Southwest Logo
2:35 pm - 9:00 pm
PUJ
-
MDW
7h 25m
1 stop
$432Southwest
Mon, Aug 31 - Thu, Sep 3
Southwest Logo
5:00 am - 1:40 pm
MDW
-
PUJ
7h 40m
1 stop
Southwest Logo
1:45 pm - 7:30 am
PUJ
-
MDW
18h 45m
2 stops
$455Southwest
Sat, Aug 29 - Sat, Sep 5
Frontier Logo
6:05 am - 2:27 pm
MDW
-
PUJ
7h 22m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$482Frontier
Mon, Aug 17 - Sat, Aug 22
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$490Frontier
Sat, Aug 29 - Sat, Sep 5
Frontier Logo
6:05 am - 2:27 pm
MDW
-
PUJ
7h 22m
1 stop
Frontier Logo
3:37 pm - 10:47 pm
PUJ
-
MDW
8h 10m
1 stop
$491Frontier
Booking Insights

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

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

What is the cheapest month to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Punta Cana is April, where tickets cost $515 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $1,285 and $1,236 respectively.

Can I save money by flying with a layover from Chicago Midway Airport 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 1 stop layover the cheapest option at $570 on average.

Expert advice

Expert advice for your flight from Midway 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
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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 season

January

Cheapest flight

$173
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 43% increase in price.
Flight from Chicago Midway Airport to Punta Cana

When to book flights from Midway to Punta Cana

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

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Punta Cana was $173 for a one-way ticket and $380 for a round-trip.

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

    A passport is required to fly from Chicago Midway Airport to Punta Cana.

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

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

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

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

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

    You can catch a nonstop flight from Chicago Midway Airport to Punta Cana on Monday, Thursday, Friday, and Sunday.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Punta Cana are Southwest and Frontier. With an average price for the route of $976 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $960 and an overall rating of 5.6.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to Punta Cana.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PUJ can sometimes prove cheaper using this method.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $338 or less one-way.

Prefer to fly direct from Chicago Midway Airport 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 Midway to Punta Cana.
Find which airlines fly direct from Chicago Midway Airport to Punta Cana Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Punta Cana

Monday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Punta Cana to Chicago Midway

Monday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway 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 Midway 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 4229 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

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 !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

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.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

I have come to accept Frontier as an absolute no-frills airline, paying for everything I want. A 4.5-hour flight should provide me with a complimentary beverage—rather, $4.9x for a soda. Or a bottle of water ought to be extended at no cost. 4 beers are on the menu, but only 1 type of beer is available (at $9.95). Also, so many restrictions to using a voucher from Barclay‘s Credit Card. Finally, try to reach a live agent for Frontier- impossible!

I liked the speed of boarding and getting to destination and flexibility to change seats when available. The flight attendants were very rude, however.

I like that the flight was not overcrowded, and I felt had space to spread out a little more. The flight was smooth for the most part no major turbulence. The crew was pretty good accommodating and professional.. the fellow passengers were cool as well… all good! Snacks always makes things better, but of course there were no snacks.

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

Other airlines flying from Midway to Punta Cana

Flights from the other most popular airlines that fly from Midway to Punta Cana according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.