MDW - PUJ

$145 Find Cheap Flights from Chicago Midway Airport 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 Midway to Punta Cana departing on 3/1. 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, 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 Chicago to Punta Cana, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$314
Overall average: $520
Multiple Airlines
pt. 2/6pt. 2/13
MDW - PUJ • 1 stop
Cheapest non-stop
$383
Southwest
pt. 3/6śr. 3/11
MDW - PUJ • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's user-friendly setup eases your departure.
Fill out the E-Ticket form for a smooth Punta Cana entry.
Expert advice
Expert advice
Expert advice
Expert advice
When to travel
October
Cheapest • 36% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
1 day a week
There are direct flights from Midway to Punta Cana 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
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 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

pt., lut 6 - pt., lut 13
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
$314Multiple Airlines
pt., lut 6 - pt., lut 13
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
$325Multiple Airlines
sob., lut 21 - sob., lut 28
Frontier Logo
6:00 am - 3:36 pm
MDW
-
PUJ
7h 36m1 stop
Frontier Logo
4:52 pm - 7:59 pm
PUJ
-
MDW
29h 07m1 stop
$327Frontier
pon., sty 19 - sob., sty 24
Multiple Airlines Logo
7:20 pm - 5:33 pm
MDW
-
PUJ
20h 13m1 stop
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$331Multiple Airlines
sob., lut 21 - sob., lut 28
Frontier Logo
8:00 am - 4:15 pm
MDW
-
PUJ
30h 15m2 stops
Frontier Logo
4:52 pm - 7:59 pm
PUJ
-
MDW
29h 07m1 stop
$337Frontier
pt., sty 9 - pt., sty 16
Multiple Airlines Logo
3:01 pm - 4:31 pm
MDW
-
PUJ
23h 30m1 stop
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
$342Multiple Airlines
pon., sty 5 - pon., sty 12
Multiple Airlines Logo
3:10 pm - 2:09 pm
MDW
-
PUJ
20h 59m1 stop
Multiple Airlines Logo
6:49 pm - 12:02 am
PUJ
-
MDW
31h 13m2 stops
$345Multiple Airlines
sob., sty 17 - sob., sty 24
Frontier Logo
6:10 am - 3:07 pm
MDW
-
PUJ
6h 57m1 stop
Frontier Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$346Frontier
sob., lut 21 - sob., lut 28
Frontier Logo
6:00 am - 3:36 pm
MDW
-
PUJ
7h 36m1 stop
Frontier Logo
4:52 pm - 7:59 pm
PUJ
-
MDW
29h 07m1 stop
$348Frontier
ndz., sty 18 - sob., sty 24
Multiple Airlines Logo
8:19 pm - 11:40 am
MDW
-
PUJ
13h 21m1 stop
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$349Multiple Airlines
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 October, where tickets cost $482 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $1,029 and $925 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.

No, with an average price for the route of $403, prices are generally cheapest when you fly direct.

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.
Airports
MDW

Midway offers a user-friendly experience with shorter security lines than O'Hare, making it ideal for a smooth departure.

PUJ

Complete the E-Ticket immigration form before arriving at PUJ to ensure a smooth entry process.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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 seasonAugust
Cheapest flight$145
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 18% lower on average.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Punta Cana was $145 for a one-way ticket and $314 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, and Delta 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.

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

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Punta Cana.

  • 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 Saturday.

  • 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 $736 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $869 and an overall rating of 7.9.

  • 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 $381 or less round-trip.

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

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Punta Cana to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

Reviews of the top 3 airlines serving 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

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

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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.