Cheap Flight Tickets from Chicago (MDW) to Punta Cana (PUJ), Starting at $3685

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

$3685

WN Southwest Airlines • nonstop • 7h 5m

Jul 15 – Jul 30

The cheapest round trip flight from Chicago to Punta Cana (MDW-PUJ-MDW) is currently $3685

🔍 Search Flights

Cheapest Direct Flight

$3685

WN Southwest Airlines • nonstop • 7h 5m

Jul 15

The cheapest nonstop flight from Chicago to Punta Cana (MDW-PUJ) is currently $3685

🔍 Search Flights

Fastest Flight

7h 5m

The fastest nonstop flight from Chicago to Punta Cana (MDW-PUJ) takes 7h 5m

Top Airlines Flying from Chicago to Punta Cana

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

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.

Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
7h 5m
10:35 AM - 4:00 PM • nonstop
WN
Chicago → Punta Cana
7h 25m
2:40 PM - 6:25 PM • nonstop
$3685
Southwest Airlines
Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
23h 55m
9:10 PM - 12:45 PM • 1 stop
WN
Chicago → Punta Cana
7h 25m
2:40 PM - 6:25 PM • nonstop
$3734
Southwest Airlines
Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
29h 15m
5:30 PM - 12:25 PM • 1 stop
WN
Chicago → Punta Cana
7h 25m
2:40 PM - 6:25 PM • nonstop
$3734
Southwest Airlines
Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
7h 5m
10:35 AM - 4:00 PM • nonstop
WN
Chicago → Punta Cana
27h 10m
3:30 PM - 7:00 AM • 2 stops
$3845
Southwest Airlines
Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
30h 35m
6:05 PM - 1:40 PM • 2 stops
WN
Chicago → Punta Cana
7h 25m
2:40 PM - 6:25 PM • nonstop
$3845
Southwest Airlines
Jul 15 - Jul 30, Economy
WN
Chicago → Punta Cana
12h 5m
5:10 AM - 1:35 PM • 1 stop
WN
Chicago → Punta Cana
19h 5m
1:25 PM - 12:10 AM • 2 stops
$3895
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 5:10 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 3845
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 9:10 pm

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*