MDW - PUJ

$151 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 4/13. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$359
Overall average: $781
Frontier
Sat 5/2Sat 5/9
MDW - PUJ • 1 stop
Cheapest non-stop
$506
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 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 76% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $459 (round-trip)
Shortest trip • 6h 42m (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

Sat, May 2 - Sat, May 9
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$359Frontier
Mon, Apr 13 - Sat, Apr 18
Frontier Logo
6:00 am - 1:45 pm
MDW
-
PUJ
6h 45m
1 stop
Frontier Logo
11:07 am - 7:59 am
PUJ
-
MDW
21h 52m
1 stop
$377Frontier
Tue, May 12 - Tue, May 19
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
3:35 pm - 11:09 am
PUJ
-
MDW
20h 34m
1 stop
$379Frontier
Sat, May 2 - Sat, May 9
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$380Frontier
Sat, May 2 - Thu, May 7
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
3:35 pm - 11:09 am
PUJ
-
MDW
20h 34m
1 stop
$382Frontier
Mon, May 4 - Sat, May 9
Frontier Logo
2:15 pm - 2:24 pm
MDW
-
PUJ
23h 09m
1 stop
Frontier Logo
3:35 pm - 11:12 am
PUJ
-
MDW
20h 37m
1 stop
$383Frontier
Sat, Apr 18 - Thu, Apr 30
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
1:05 pm - 10:19 pm
PUJ
-
MDW
10h 14m
2 stops
$384Frontier
Sat, Apr 18 - Tue, Apr 21
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
9:13 pm - 7:26 am
PUJ
-
MDW
35h 13m
2 stops
$385Frontier
Sat, Apr 18 - Sat, Apr 25
Frontier Logo
6:00 am - 1:54 pm
MDW
-
PUJ
6h 54m
1 stop
Frontier Logo
3:04 pm - 9:58 am
PUJ
-
MDW
19h 54m
1 stop
$386Frontier
Sat, Apr 11 - Tue, Apr 21
Multiple Airlines Logo
6:30 am - 4:31 pm
MDW
-
PUJ
9h 01m
1 stop
Multiple Airlines Logo
7:10 pm - 1:00 pm
PUJ
-
MDW
18h 50m
1 stop
$388Multiple 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 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 $670 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 seasonAugust
Cheapest flight$151
Best time to beat the crowds with an average 3% 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 $151 for a one-way ticket and $359 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.

  • 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?

    There are nonstop flights from Chicago Midway Airport 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 $659 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 $571 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

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 4320 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

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.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

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.