MDW - PUJ

$156 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 10/25. 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

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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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, Oct 24 - Sat, Nov 1
Multiple Airlines Logo
12:18 pm - 4:31 pmMDW-PUJ
27h 13m1 stop
Multiple Airlines Logo
9:38 am - 9:22 pmPUJ-MDW
12h 44m1 stop
$334Multiple Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Southwest Logo
5:25 am - 2:10 pmMDW-PUJ
7h 45m1 stop
Southwest Logo
1:40 pm - 10:35 pmPUJ-MDW
9h 55m1 stop
$357Southwest
Find Deal
Sun, Oct 26 - Thu, Oct 30
Southwest Logo
6:25 am - 2:20 pmMDW-PUJ
6h 55m1 stop
Southwest Logo
2:45 pm - 11:15 pmPUJ-MDW
9h 30m2 stops
$361Southwest
Find Deal
Fri, Oct 24 - Sat, Nov 1
Multiple Airlines Logo
12:18 pm - 4:31 pmMDW-PUJ
27h 13m1 stop
Multiple Airlines Logo
9:38 am - 6:39 pmPUJ-MDW
10h 01m2 stops
$362Multiple Airlines
Find Deal
Sun, Nov 16 - Thu, Nov 20
Delta Logo
6:00 am - 4:18 pmMDW-PUJ
8h 18m1 stop
Delta Logo
2:38 pm - 11:32 pmPUJ-MDW
10h 54m1 stop
$363Delta
Find Deal
Sun, Jan 11 - Thu, Jan 15
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
$365Delta
Find Deal
Tue, Nov 11 - Tue, Nov 18
Delta Logo
12:47 pm - 1:26 pmMDW-PUJ
22h 39m2 stops
Delta Logo
5:03 pm - 11:32 pmPUJ-MDW
8h 29m1 stop
$368Delta
Find Deal
Sun, Jan 11 - Thu, Jan 15
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
Delta Logo
5:18 pm - 6:34 pmPUJ-MDW
27h 16m2 stops
$370Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
Frontier Logo
3:32 pm - 10:47 pmPUJ-MDW
8h 15m1 stop
$383Frontier
Find Deal
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
6:00 am - 2:56 pmMDW-PUJ
6h 56m1 stop
Frontier Logo
4:11 pm - 11:25 pmPUJ-MDW
9h 14m1 stop
$385Frontier
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Top airlines
Southwest
Cheapest • from $357 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 34% 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
Cheapest round-trip
$334
Overall average: $482
Multiple Airlines
Fri 10/24Sat 11/1
MDW - PUJ • 1 stop
Cheapest non-stop
$482
Southwest
Sat 1/10Sat 1/17
MDW - PUJ • Non-stop
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!
Expert advice

Expert advice for your flight from Midway to Punta Cana

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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.

Read more about MDWby Stefanie Waldek
PUJ

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

Read more about PUJby Mark Chesnut
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
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 $1,039 and $912 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.

Good to know

Low seasonAugust
Cheapest flight$156
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 16% 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 $156 for a one-way ticket and $334 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?

    Only American Airlines offers 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 737-900 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.

  • 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 $743 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 $802 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 $126 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

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.
8.0
SouthwestOverall score based on 4242 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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