PUJ - MDW

$149 Find Cheap Flights from Punta Cana to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Punta Cana to Midway departing on 3/11. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Punta Cana to Chicago, 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 Punta Cana to Chicago, 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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Everything you should know

Cheapest round-trip
$399
Multiple Airlines
Sun 2/8Sun 2/15
PUJ - MDW • 2 stops
Cheapest non-stop
$754
Southwest
Thu 3/12Thu 3/19
PUJ - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Check in via app for a quicker departure at PUJ.
Use the CTA Orange Line from MDW for easy downtown access.
Expert advice
Expert advice
Expert advice
Expert advice
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 Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

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

Sun, Feb 8 - Sun, Feb 15
Multiple Airlines Logo
5:47 pm - 11:45 am
PUJ
-
MDW
19h 58m
2 stops
Multiple Airlines Logo
6:15 am - 11:40 am
MDW
-
PUJ
27h 25m
1 stop
$399Multiple Airlines
Sun, May 10 - Sat, May 16
Multiple Airlines Logo
7:10 pm - 1:00 pm
PUJ
-
MDW
18h 50m
1 stop
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
PUJ
8h 00m
1 stop
$459Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
2:40 pm - 9:00 pm
PUJ
-
MDW
8h 20m
1 stop
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$472Southwest
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
2:40 pm - 7:50 am
PUJ
-
MDW
19h 10m
2 stops
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$476Southwest
Sun, May 10 - Sat, May 16
Frontier Logo
8:44 pm - 10:19 pm
PUJ
-
MDW
26h 35m
2 stops
Frontier Logo
6:00 am - 1:46 pm
MDW
-
PUJ
6h 46m
1 stop
$524Frontier
Thu, Mar 12 - Thu, Mar 19
Multiple Airlines Logo
9:38 am - 10:19 pm
PUJ
-
MDW
13h 41m
2 stops
Multiple Airlines Logo
7:30 am - 4:26 pm
MDW
-
PUJ
7h 56m
1 stop
$525Multiple Airlines
Sat, Feb 21 - Mon, Mar 2
Southwest Logo
3:35 pm - 6:35 pm
PUJ
-
MDW
5h 00mnonstop
Southwest Logo
5:30 am - 2:30 pm
MDW
-
PUJ
7h 00m
1 stop
$536Southwest
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
2:40 pm - 7:50 am
PUJ
-
MDW
19h 10m
2 stops
Southwest Logo
6:00 am - 1:35 pm
MDW
-
PUJ
6h 35m
1 stop
$580Southwest
Sun, May 10 - Sat, May 16
Southwest Logo
4:15 pm - 11:40 pm
PUJ
-
MDW
8h 25m
1 stop
Southwest Logo
9:40 am - 3:00 pm
MDW
-
PUJ
4h 20mnonstop
$593Southwest
Sat, Feb 21 - Mon, Mar 2
Multiple Airlines Logo
3:19 pm - 9:33 pm
PUJ
-
MDW
8h 14m
1 stop
Multiple Airlines Logo
9:22 pm - 4:36 pm
MDW
-
PUJ
17h 14m
2 stops
$612Multiple Airlines
Booking Insights

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

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

Can I save money by flying with a layover from Punta Cana to Chicago Midway Airport?

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 $443, prices are generally cheapest when you fly direct.

Find deals
Expert advice

Expert advice for your flight from Punta Cana to Midway

 
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.

Read more
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.

Read more

Good to know

Cheapest flight$149
Flight from Punta Cana to Chicago Midway Airport

When to book flights from Punta Cana to Midway

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

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

    In the last 3 days, the lowest price for a flight from Punta Cana to Chicago Midway Airport was $149 for a one-way ticket and $399 for a round-trip.

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

    Yes

  • Which airports will I be using when flying from Punta Cana to Chicago Midway Airport?

    Punta Cana and Chicago Midway Airport are both served by 1 main airport. You will leave Punta Cana from Punta Cana and will be arriving at Chicago Midway.

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

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

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

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

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

    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 Punta Cana to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Punta Cana to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Punta Cana 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 Punta Cana to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Punta Cana with another airline. Booking your flights between Punta Cana and MDW 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 Punta Cana to Chicago Midway Airport?

    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 Chicago Midway Airport from Punta Cana 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 Punta Cana to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $464 or less one-way.

Prefer to fly direct from Punta Cana to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Punta Cana to Chicago Midway.
Find which airlines fly direct from Punta Cana Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

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

Information on your arrival and departure airports

Punta Cana (PUJ)
Midway (MDW)