MDW - PUJ

$166 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 8/11. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$333
Typical prices: $834-$669
Frontier
Fri 5/15Wed 5/27
MDW - PUJ • 1 stop
Cheapest non-stop
$679
Southwest
Sat 5/16Sat 5/23
MDW - PUJ • Non-stop
Advice from real travelers
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
Nonstop flights
You can fly direct with Southwest. Average duration is 4h 20m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 74% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $459 (round-trip)
Shortest trip • 6h 33m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
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 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

Fri, May 15 - Wed, May 27
Frontier Logo
4:52 pm - 9:18 am
MDW
-
PUJ
15h 26m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$333Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
11:45 am - 10:02 pm
PUJ
-
MDW
11h 17m
2 stops
$336Frontier
Tue, May 12 - Wed, May 27
Frontier Logo
6:00 am - 8:19 pm
MDW
-
PUJ
13h 19m
2 stops
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$360Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$362Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
11:45 am - 10:02 pm
PUJ
-
MDW
11h 17m
2 stops
$363Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
11:45 am - 10:02 pm
PUJ
-
MDW
11h 17m
2 stops
$368Frontier
Fri, May 15 - Thu, May 28
Frontier Logo
4:52 pm - 9:18 am
MDW
-
PUJ
15h 26m
1 stop
Frontier Logo
11:45 am - 10:02 pm
PUJ
-
MDW
11h 17m
2 stops
$374Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:00 am - 10:57 am
MDW
-
PUJ
27h 57m
2 stops
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$376Frontier
Sat, May 16 - Wed, May 27
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$377Frontier
Fri, May 15 - Fri, May 29
Frontier Logo
4:52 pm - 9:18 am
MDW
-
PUJ
15h 26m
1 stop
Frontier Logo
11:45 am - 10:02 pm
PUJ
-
MDW
11h 17m
2 stops
$379Frontier
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.

How much is a round-trip flight from Chicago Midway Airport 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 Midway Airport to Punta Cana departing in May.

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 March and November, where the average cost of round-trip tickets is $1,125 and $1,029 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 $562 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 seasonJanuary
Cheapest flight$166
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 21% 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 $166 for a one-way ticket and $333 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, JetBlue, 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 Monday, Thursday, Friday, and 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 $661 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 $779 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 $555 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

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Punta Cana to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

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.
8.0
SouthwestOverall score based on 4314 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

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.

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.