Cheap Flight Tickets from Chicago (MDW) to Punta Cana (PUJ), Starting at $168

Good to Know: Cheapest and Fastest MDW - PUJ Flights

Useful information for finding best airline tickets from Chicago Midway International to Punta Cana International on your next trip.

Cheapest Round Trip Flight

$324

WN Southwest Airlines • 2 stops • 30h 55m

Oct 20 – Oct 27

The cheapest round trip flight from Chicago to Punta Cana (MDW-PUJ-MDW) is currently $324

🔍 Search Flights

Cheapest One way Flight

$168

WN Southwest Airlines • 2 stops • 38h 55m

Oct 19

The cheapest one way flight from Chicago to Punta Cana (MDW-PUJ) is currently $168

🔍 Search Flights

Cheapest Direct Flight

$849

AA American Airlines • nonstop • 7h 18m

Oct 20

The cheapest nonstop flight from Chicago to Punta Cana (MDW-PUJ) is currently $849

🔍 Search Flights

Fastest Flight

7h 18m

The fastest nonstop flight from Chicago to Punta Cana (MDW-PUJ) takes 7h 18m

Latest Flight Deals from Chicago (MDW) to Punta Cana (PUJ)

Compare and book low fare round-trip air tickets from Chicago to Punta Cana. Ideal for travelers with confirmed return itineraries.

Oct 20 - Oct 27, Economy
WN
Chicago → Punta Cana
30h 55m
4:30 PM - 12:25 PM • 2 stops
WN
Chicago → Punta Cana
12h 20m
2:45 PM - 9:25 PM • 1 stop
$324
Southwest Airlines
Oct 20 - Oct 27, Economy
WN
Chicago → Punta Cana
28h 45m
6:00 PM - 12:25 PM • 2 stops
WN
Chicago → Punta Cana
12h
1:25 PM - 7:45 PM • 1 stop
$369
Southwest Airlines
Oct 20 - Oct 27, Economy
AA
Chicago → Punta Cana
11h 44m
- • 1 stop
UA
Chicago → Punta Cana
13h 58m
- • 1 stop
$620
American Airlines
Oct 20 - Oct 27, Economy
AA
Chicago → Punta Cana
35h 22m
- • 1 stop
UA
Chicago → Punta Cana
13h 58m
- • 1 stop
$638
American Airlines
Oct 20 - Oct 27, Economy
AA
Chicago → Punta Cana
30h 35m
- • 1 stop
UA
Chicago → Punta Cana
13h 58m
- • 1 stop
$645
American Airlines
Oct 20 - Oct 27, Economy
WN
Chicago → Punta Cana
45h 40m
9:05 AM - 1:45 PM • 1 stop
WN
Chicago → Punta Cana
12h
1:25 PM - 7:45 PM • 1 stop
$712
Southwest Airlines

Fly from Chicago to Punta Cana with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Punta Cana? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Punta Cana Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to PUJ?
The most popular airline flying from Chicago to Punta Cana are
Can I fly from MDW to PUJ non-stop?
Yes, you can fly MDW to PUJ non-stop on
Which airlines fly nonstop between Chicago and Punta Cana?
The non-stop flights between Chicago and Punta Cana are .
What’s the earliest departure time from MDW to PUJ Airport?
The earliest flight leaves MDW at 8:25 am and lands in PUJ - Punta Cana International
What are the airports in Punta Cana?
PUJ
Can I make changes to my Chicago to Punta Cana flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to PUJ?
Read the fare rules of the Chicago to Punta Cana air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Punta Cana?
operate flights between Chicago and Punta Cana
How long does a flight from Chicago to Punta Cana take?
It takes approximately 5 hour to fly non-stop from MDW to PUJ, which is 1965.7 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Punta Cana (PUJ) ?
In the past couple of days, the cheapest tickets to PUJ from MDW were found on WN : USD 174
Do I need a passport to fly between MDW and PUJ?
Yes
What’s the latest departure time from MDW to PUJ ?
The last flight leaves MDW at 7:2900 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to puj?
For a round-trip economy flight from Chicago Midway International Airport (mdw) to Punta Cana International Airport (puj) with 6 passengers, consider booking with Delta Airlines (DL) to find the cheapest airfares. Please note that the cheapest flights may vary depending on the travel dates and availability. It's recommended to book in advance, ideally 18 days prior to your trip, to secure the best budget-friendly flights. To find the most up-to-date and affordable airfares, visit fareleaders.com and compare prices across airlines.
What's the popular airline to fly from mdw to puj?
Southwest Airlines offers flights from Chicago Midway International Airport (mdw) to Punta Cana International Airport (puj) for round-trip travel, with a focus on providing budget-friendly airfares and convenient travel options. Low fares on this route can be achieved with advance booking, typically 18 days in advance. For a group of 6 passengers, Southwest Airlines is a popular choice for a round-trip journey.
What's the cheapest day of the week to fly from mdw to puj?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Punta Cana International Airport (puj) is Sunday. Flying on Sundays can result in budget-friendly flights and airfares. Consider booking your round-trip flights in advance, ideally 18 days prior to your departure, to secure the best deals.
What's the cheapest month to fly from mdw to puj?
The cheapest month to fly from Chicago Midway International (mdw) to Punta Cana International (puj) is November, as it is typically the low season for air travel to the Caribbean. You can expect to find budget-friendly flights during this time. November is a great time to save on airfares, making it an ideal month for your round-trip journey.
Which airline/airlines fly from mdw to puj?
The airlines that fly from Chicago Midway International Airport (mdw) to Punta Cana International Airport (puj) include Air Transat, American Airlines, Volaris Airline, JetBlue Airways, Copa Airlines, Delta Airlines, Porter Airline, Southwest Airlines, Frontier Airlines, and United Airlines.
What is the cheapest airfare from Milwaukee to Punta Cana International Airport?
The cheapest airfare from Milwaukee to Punta Cana International Airport can be found on Delta Airlines (DL) with fares starting from $400.
How far in advance should I book my flight to get the best fares?
It is recommended to book your flight at least 18 days in advance to get the best fares.
Can I book a round trip flight from Chicago Midway International Airport to Punta Cana International Airport?
Yes, you can book a round trip flight from Chicago Midway International Airport to Punta Cana International Airport.
What is the difference between an economy and a full fare ticket?
An economy ticket is a basic ticket that includes only the essentials, while a full fare ticket includes additional amenities such as checked baggage and priority boarding.
How many stops are there on flights from Milwaukee to Punta Cana International Airport?
There are 0 stops on flights from Milwaukee to Punta Cana International Airport.
Can I book a one way flight from Punta Cana International Airport to Milwaukee?
Yes, you can book a one way flight from Punta Cana International Airport to Milwaukee.
What is the best time to book airfare for a July trip?
The best time to book airfare for a July trip is in November, as it is considered the cheapest month to book.
How do I find the best airline for my travel needs?
You can find the best airline for your travel needs by comparing prices and services on websites such as fareleaders.com.
How can I get the best deals on airfare for my next trip?
You can get the best deals on airfare for your next trip by booking in advance, using flight comparison websites, and being flexible with your travel dates.
Can I book a flight with a specific agency for my travel needs?
Yes, you can book a flight with a specific agency for your travel needs, but it may not always be the cheapest option.

Chicago (MDW) to Punta Cana (PUJ): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Punta Cana International , Punta Cana, DO
Distance 1966 miles

More Flight Options for Chicago (MDW) and Punta Cana (PUJ)

Why Fareleaders for MDW to PUJ Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Punta Cana flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to PUJ flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Punta Cana flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Punta Cana (PUJ)
Terms and Conditions*