What is the most punctual flight time for Chicago to Punta Cana flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What airlines fly to Punta Cana?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Punta Cana from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 75% of people opting to fly with this airline when traveling to Punta Cana. Keep in mind that there are 3 different airlines that fly to Punta Cana on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago Midway to Punta Cana?

Frontier, Delta, and Southwest are the most popular carriers operating from Chicago Midway to Punta Cana

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to Punta Cana delayed?

Historically, on average around 20% of flights between Chicago and Punta Cana have experienced a delay on any given week. The average delay length over the past 12 months has been 112 minutes.

Which airline has the best punctuality record on Chicago to Punta Cana flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?

Prices for flights from Chicago Midway Airport to Punta Cana Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?

As of October 2025, there are 3 operators available to choose from for flights from Chicago Midway Airport to Punta Cana Airport.

How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Punta Cana Airport.

What documentation or ID do you need to fly to Punta Cana Airport?

The necessary travel and health documents for your Punta Cana Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$133 Cheap Flights from Chicago Midway Airport to Punta Cana in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Punta Cana

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:12 am - 4:50 pmMDW-PUJ

32h 38m2 stops

4:19 pm - 10:12 pmPUJ-MDW

7h 53m1 stop

$306Multiple Airlines

Find Deal

qua, dez 24 - qua, dez 31

2:59 pm - 6:38 pmMDW-PUJ

25h 39m1 stop

9:38 am - 10:30 pmPUJ-MDW

14h 52m1 stop

$314Multiple Airlines

Find Deal

sáb, dez 6 - sáb, dez 13

2:16 pm - 7:54 pmMDW-PUJ

27h 38m1 stop

9:38 am - 9:53 pmPUJ-MDW

14h 15m1 stop

$317Multiple Airlines

Find Deal

qui, dez 4 - qui, dez 11

2:59 pm - 6:38 pmMDW-PUJ

25h 39m1 stop

9:38 am - 10:30 pmPUJ-MDW

14h 52m1 stop

$319Multiple Airlines

Find Deal

sáb, dez 6 - sáb, dez 13

6:15 am - 9:29 pmMDW-PUJ

13h 14m1 stop

1:49 pm - 9:13 amPUJ-MDW

21h 24m1 stop

$322Multiple Airlines

Find Deal

seg, jan 5 - sáb, jan 10

6:00 am - 3:39 pmMDW-PUJ

7h 39m1 stop

5:04 pm - 11:47 pmPUJ-MDW

8h 43m1 stop

$338Delta

Find Deal

ter, dez 9 - qua, dez 10

6:45 pm - 2:30 pmMDW-PUJ

17h 45m1 stop

5:11 pm - 8:54 amPUJ-MDW

17h 43m1 stop

$342Delta

Find Deal

dom, fev 22 - qua, fev 25

8:15 am - 2:35 pmMDW-PUJ

4h 20mnonstop

3:00 pm - 5:55 pmPUJ-MDW

4h 55mnonstop

$353Southwest

Find Deal

sáb, jan 24 - sáb, jan 31

5:10 am - 2:00 pmMDW-PUJ

6h 50m1 stop

3:00 pm - 5:55 pmPUJ-MDW

4h 55mnonstop

$358Southwest

Find Deal

sáb, jan 24 - sáb, jan 31

6:12 am - 10:27 amMDW-PUJ

26h 15m1 stop

4:19 pm - 10:12 pmPUJ-MDW

7h 53m1 stop

$369Frontier

Find Deal

qua, dez 24 - qua, dez 31

Delta flights from Chicago Midway Airport to Punta Cana

Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets

Delta

Dec 9

MDW6:00 amChicago Midway

7h 39m

1 stop

PUJ3:39 pmPunta Cana

Dec 10

PUJ5:04 pmPunta Cana

8h 43m

1 stop

MDW11:47 pmChicago Midway

$338

Find similar

Delta

Feb 22

MDW6:45 pmChicago Midway

17h 45m

1 stop

PUJ2:30 pmPunta Cana

Feb 25

PUJ5:11 pmPunta Cana

17h 43m

1 stop

MDW8:54 amChicago Midway

$342

Find similar

Delta

Feb 24

MDW5:25 pmChicago Midway

17h 55m

2 stops

PUJ1:20 pmPunta Cana

Feb 26

PUJ5:11 pmPunta Cana

17h 43m

1 stop

MDW8:54 amChicago Midway

$346

Find similar

Southwest flights from Chicago Midway Airport to Punta Cana

Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets

Southwest

Jan 24

MDW8:15 amChicago Midway

4h 20m

PUJ2:35 pmPunta Cana

Jan 31

PUJ3:00 pmPunta Cana

4h 55m

MDW5:55 pmChicago Midway

$353

Find similar

Southwest

Jan 24

MDW5:10 amChicago Midway

6h 50m

1 stop

PUJ2:00 pmPunta Cana

Jan 31

PUJ3:00 pmPunta Cana

4h 55m

MDW5:55 pmChicago Midway

$358

Find similar

Southwest

Nov 29

MDW8:30 amChicago Midway

4h 20m

PUJ2:50 pmPunta Cana

Dec 6

PUJ5:00 pmPunta Cana

7h 35m

1 stop

MDW10:35 pmChicago Midway

$359

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

qua 12/24

6:12 am-4:50 pm

2 stops32h 38m

Punta Cana

qua 12/31

4:19 pm-10:12 pm

1 stop7h 53m

$306

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb 12/6

2:59 pm-6:38 pm

1 stop25h 39m

Punta Cana

sáb 12/13

9:38 am-10:30 pm

1 stop14h 52m

$314

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

qui 12/4

2:16 pm-7:54 pm

1 stop27h 38m

Punta Cana

qui 12/11

9:38 am-9:53 pm

1 stop14h 15m

$317

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb 12/6

2:59 pm-6:38 pm

1 stop25h 39m

Punta Cana

sáb 12/13

9:38 am-10:30 pm

1 stop14h 52m

$319

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

seg 1/5

6:15 am-9:29 pm

1 stop13h 14m

Punta Cana

sáb 1/10

1:49 pm-9:13 am

1 stop21h 24m

$322

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

ter 12/9

6:00 am-3:39 pm

1 stop7h 39m

Punta Cana

qua 12/10

5:04 pm-11:47 pm

1 stop8h 43m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dom 2/22

6:45 pm-2:30 pm

1 stop17h 45m

Punta Cana

qua 2/25

5:11 pm-8:54 am

1 stop17h 43m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb 1/24

8:15 am-2:35 pm

Nonstop4h 20m

Punta Cana

sáb 1/31

3:00 pm-5:55 pm

Nonstop4h 55m

$353

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb 1/24

5:10 am-2:00 pm

1 stop6h 50m

Punta Cana

sáb 1/31

3:00 pm-5:55 pm

Nonstop4h 55m

$358

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

qua 12/24

6:12 am-10:27 am

1 stop26h 15m

Punta Cana

qua 12/31

4:19 pm-10:12 pm

1 stop7h 53m

$369

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How to get the cheapest flight ticket from Chicago Midway Airport to Punta Cana

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

What is the cheapest month to fly to Punta Cana?

If you’re not able to fly to Punta Cana in October, then February is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during February average around $518.

What is the cheapest day to depart on your flight to Punta Cana?

The cheapest day to depart from Chicago Midway Airport to Punta Cana is on a Monday when prices can be found for as low as $502. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Sunday is $558.

What is the cheapest time of day to depart on your flight to Punta Cana?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Punta Cana when you can find flight prices for as low as $341. Flying to Punta Cana at noon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $541 per ticket.

What is the cheapest Chicago Midway to Punta Cana flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Punta Cana flight prices

What cabin class options are available on Chicago Midway to Punta Cana flights?

There is only 1 cabin class available to choose from on Chicago Midway to Punta Cana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago Midway Airport to Punta Cana

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Punta Cana according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Punta Cana (MDW to PUJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Punta Cana

Best Price Found	$919
Fastest flight time	4h 15m
Direct flights	Every day
Airports in Punta Cana	1 airport

The best flight deal from Chicago Midway Airport to Punta Cana found on momondo in the last 72 hours is $919

The fastest flight from Chicago Midway Airport to Punta Cana takes 4h 15m

Direct flights go from Chicago Midway Airport to Punta Cana every day.

There is 1 airport near Punta Cana: Punta Cana (PUJ)

Search flight deals

How far is Chicago Midway to Punta Cana by plane?
The straight-line distance from Chicago Midway to Punta Cana is 1957.5 mi. A reasonable flight in good conditions will take 4h 20m.
When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?
Prices for flights from Chicago Midway Airport to Punta Cana Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?
As of October 2025, there are 3 operators available to choose from for flights from Chicago Midway Airport to Punta Cana Airport.
How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Punta Cana Airport.
What documentation or ID do you need to fly to Punta Cana Airport?
The necessary travel and health documents for your Punta Cana Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Punta Cana?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Punta Cana is Boeing 737 MAX 8 (41.30% of total bookings). The next most popular plane models are Boeing 737 (15.22%), Boeing 737-800 (10.87%), and Airbus A321-100/200 (6.52%).
What is the most popular airline from Chicago Midway Airport to Punta Cana?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Punta Cana is Southwest, representing 77% of all bookings. The subsequent popular airlines are Frontier at 17% and Delta at 6%.

Best airlines flying from Chicago Midway Airport to Punta Cana

Compare and see reviews for airlines that fly from Chicago Midway Airport to Punta Cana with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $370	Free Cancellation	Rating 5.8 3,123 reviews	Search Frontier flights
Southwest	PriceFrom $495	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
Delta	PriceFrom $539	Free Cancellation	Rating 7.9 7,993 reviews	Search Delta flights

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Punta Cana?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Punta Cana from Chicago.

Can I find flights from Chicago to Punta Cana with flexible booking policies on momondo?

All flight searches from Chicago to Punta Cana on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Punta Cana?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Punta Cana.

I’m not ready to book a flight from Chicago to Punta Cana right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Punta Cana, momondo offers a useful price alert feature which will track prices for flights to Punta Cana from Chicago and alert you when they change.

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Cheap flights from Chicago Midway Airport to Punta Cana from $133

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Find the cheapest flights from Chicago Midway Airport to Punta Cana

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Delta flights from Chicago Midway Airport to Punta Cana

Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets

Southwest flights from Chicago Midway Airport to Punta Cana

Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets

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Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana that are best for you.

See travel insights to Punta Cana from

How to get the cheapest flight ticket from Chicago Midway Airport to Punta Cana

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Punta Cana?

If you’re not able to fly to Punta Cana in October, then February is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during February average around $518.

What is the cheapest day to depart on your flight to Punta Cana?

What is the cheapest time of day to depart on your flight to Punta Cana?

What is the cheapest Chicago Midway to Punta Cana flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Punta Cana flight prices

What cabin class options are available on Chicago Midway to Punta Cana flights?

There is only 1 cabin class available to choose from on Chicago Midway to Punta Cana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from Chicago Midway to Punta Cana?

Frontier, Delta, and Southwest are the most popular carriers operating from Chicago Midway to Punta Cana

What airlines fly to Punta Cana?

How often are flights from Chicago to Punta Cana delayed?

Historically, on average around 20% of flights between Chicago and Punta Cana have experienced a delay on any given week. The average delay length over the past 12 months has been 112 minutes.

What is the most punctual flight time for Chicago to Punta Cana flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Punta Cana flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

When to book flights from Chicago Midway Airport to Punta Cana

Cheap Chicago Midway Airport to Punta Cana (MDW to PUJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Punta Cana

Best Price Found

Fastest flight time

Direct flights

Airports in Punta Cana

How far is Chicago Midway to Punta Cana by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?

How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?

How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?

What documentation or ID do you need to fly to Punta Cana Airport?

What is the most popular plane model from Chicago Midway Airport to Punta Cana?

What is the most popular airline from Chicago Midway Airport to Punta Cana?

Best airlines flying from Chicago Midway Airport to Punta Cana

Compare and see reviews for airlines that fly from Chicago Midway Airport to Punta Cana with momondo

Traveling to a place near Punta Cana?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Punta Cana?

Can I find flights from Chicago to Punta Cana with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Punta Cana?

I’m not ready to book a flight from Chicago to Punta Cana right now. Can momondo alert me if prices change?

An easier way to manage your Punta Cana trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the Dominican Republic

Airports servicing Dominican Republic