How often are flights from Chicago to Punta Cana delayed?

Historically, on average around 24% 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 109 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 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 72% 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?

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

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 24% of their flights experiencing any sort of delay.

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.

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 March 2026, 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.

$141 Cheap Flights from Chicago Midway Airport to Punta Cana in 2026

Q: How many flights depart from Chicago Midway Airport to Punta Cana on average per day?

1 flights are operational daily from Chicago Midway Airport to Punta Cana as of March 2026. The most popular departure time for this route is 9:00AM, with 100% of flights per day taking off at noon.

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago Midway Airport to Punta Cana

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 7:20 am

MDW

PUJ

23h 50m

2 stops

11:07 am - 7:59 am

PUJ

MDW

21h 52m

1 stop

$299Frontier

Sat, Apr 11 - Sat, Apr 18

6:00 am - 2:24 pm

MDW

PUJ

7h 24m

1 stop

9:29 pm - 11:04 am

PUJ

MDW

38h 35m

2 stops

$304Frontier

Tue, May 5 - Thu, May 7

6:00 am - 1:45 pm

MDW

PUJ

6h 45m

1 stop

9:13 pm - 10:26 pm

PUJ

MDW

26h 13m

2 stops

$306Frontier

Mon, Apr 13 - Thu, Apr 16

6:00 am - 1:45 pm

MDW

PUJ

6h 45m

1 stop

9:13 pm - 6:37 pm

PUJ

MDW

46h 24m

2 stops

$307Frontier

Mon, Apr 13 - Thu, Apr 16

11:59 am - 2:24 pm

MDW

PUJ

25h 25m

1 stop

3:35 pm - 11:12 am

PUJ

MDW

20h 37m

1 stop

$308Frontier

Sat, May 9 - Sat, May 16

6:00 am - 1:54 pm

MDW

PUJ

6h 54m

1 stop

3:35 pm - 11:09 am

PUJ

MDW

20h 34m

1 stop

$311Frontier

Sat, May 2 - Tue, May 5

6:00 am - 2:24 pm

MDW

PUJ

7h 24m

1 stop

3:35 pm - 11:04 am

PUJ

MDW

20h 29m

1 stop

$312Frontier

Tue, May 5 - Fri, May 8

2:15 pm - 2:24 pm

MDW

PUJ

23h 09m

1 stop

3:35 pm - 11:04 am

PUJ

MDW

20h 29m

1 stop

$318Frontier

Mon, May 4 - Fri, May 8

6:00 am - 1:45 pm

MDW

PUJ

6h 45m

1 stop

1:37 pm - 10:26 pm

PUJ

MDW

9h 49m

2 stops

$319Frontier

Mon, Apr 13 - Fri, Apr 17

6:00 am - 1:54 pm

MDW

PUJ

6h 54m

1 stop

3:35 pm - 11:09 am

PUJ

MDW

20h 34m

1 stop

$320Frontier

Sat, May 2 - Tue, May 5

Frontier flights from Chicago Midway Airport to Punta Cana

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

Frontier

Apr 11

MDW6:30 amChicago Midway

23h 50m

2 stops

PUJ7:20 amPunta Cana

Apr 18

PUJ11:07 amPunta Cana

21h 52m

1 stop

MDW7:59 amChicago Midway

$299

Frontier

May 5

MDW6:00 amChicago Midway

7h 24m

1 stop

PUJ2:24 pmPunta Cana

May 7

PUJ9:29 pmPunta Cana

38h 35m

2 stops

MDW11:04 amChicago Midway

$304

Frontier

Apr 13

MDW6:00 amChicago Midway

6h 45m

1 stop

PUJ1:45 pmPunta Cana

Apr 16

PUJ9:13 pmPunta Cana

26h 13m

2 stops

MDW10:26 pmChicago Midway

$306

Southwest flights from Chicago Midway Airport to Punta Cana

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

Southwest

Apr 1

MDW9:15 amChicago Midway

4h 15m

PUJ2:30 pmPunta Cana

Apr 16

PUJ1:40 pmPunta Cana

9h 40m

1 stop

MDW10:20 pmChicago Midway

$534

Southwest

Apr 1

MDW9:15 amChicago Midway

4h 15m

PUJ2:30 pmPunta Cana

Apr 16

PUJ2:05 pmPunta Cana

9h 40m

2 stops

MDW10:45 pmChicago Midway

$539

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

Cheapest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 4/11

6:30 am-7:20 am

2 stops23h 50m

Punta Cana

Sat 4/18

11:07 am-7:59 am

1 stop21h 52m

$299

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 5/5

6:00 am-2:24 pm

1 stop7h 24m

Punta Cana

Thu 5/7

9:29 pm-11:04 am

2 stops38h 35m

$304

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 4/13

6:00 am-1:45 pm

1 stop6h 45m

Punta Cana

Thu 4/16

9:13 pm-10:26 pm

2 stops26h 13m

$306

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 4/13

6:00 am-1:45 pm

1 stop6h 45m

Punta Cana

Thu 4/16

9:13 pm-6:37 pm

2 stops46h 24m

$307

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/9

11:59 am-2:24 pm

1 stop25h 25m

Punta Cana

Sat 5/16

3:35 pm-11:12 am

1 stop20h 37m

$308

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/2

6:00 am-1:54 pm

1 stop6h 54m

Punta Cana

Tue 5/5

3:35 pm-11:09 am

1 stop20h 34m

$311

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 5/5

6:00 am-2:24 pm

1 stop7h 24m

Punta Cana

Fri 5/8

3:35 pm-11:04 am

1 stop20h 29m

$312

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 5/4

2:15 pm-2:24 pm

1 stop23h 09m

Punta Cana

Fri 5/8

3:35 pm-11:04 am

1 stop20h 29m

$318

Quickest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 4/13

6:00 am-1:45 pm

1 stop6h 45m

Punta Cana

Fri 4/17

1:37 pm-10:26 pm

2 stops9h 49m

$319

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/2

6:00 am-1:54 pm

1 stop6h 54m

Punta Cana

Tue 5/5

3:35 pm-11:09 am

1 stop20h 34m

$320

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Other information

What is the cheapest month to fly to Punta Cana?

If you’re not able to fly to Punta Cana in October, then April is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during April average around $530.

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 $479. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Thursday is $566.

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

In the evening 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 $371. Flying to Punta Cana in the evening 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 $527 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.

Can stopping save me money on Chicago Midway Airport to Punta Cana flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Punta Cana.

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	$571
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 $571

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 in Punta Cana. From Chicago Midway Airport there are direct flights to 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 15m.
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 March 2026, 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 (41.85% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (12.50%), Boeing 737 (12.50%), and Boeing 737-900 (9.24%).
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 72% of all bookings. The subsequent popular airlines are Frontier at 22% and Delta at 7%.

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 5.7 3,020 reviews	Search Frontier flights
Southwest	PriceFrom $418	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest flights
Delta	PriceFrom $539	Free Cancellation	Rating 7.9 8,318 reviews	Search Delta flights

Southwest Flights From Chicago Midway Airport to Punta Cana
Southwest operates around 7 flights from Chicago Midway Airport to Punta Cana every week. The average price of these flights found in the last 72 hours has been $659, but momondo users have found Southwest deals from Chicago Midway Airport to Punta Cana from as low as $418 round-trip. Southwest has been scored 8.0/10 in 4,324 reviews.

Bavaro

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Wed 4/22

Wed 4/29

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Dominican Republic

Nearby airports

Airlines

Cabin classes

Other Dominican Republic destinations

Other flights from Chicago Midway Airport

Complete your trip

Feeling lucky

Airports servicing Dominican Republic

Nagua Samaná El Catey Airport

Puerto Plata Airport

La Romana Airport

Santo Domingo Las Americas Airport

Santiago de los Caballeros Airport

Dominican North Coast Airport

Cheap flights from Chicago Midway Airport to Punta Cana from $141

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Punta Cana

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago Midway Airport to Punta Cana

Our best Frontier 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

momondo Fare Finder

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

What is the cheapest month to fly to Punta Cana?

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?

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

Can stopping save me money on Chicago Midway Airport to Punta Cana flights?

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

What airlines fly to Punta Cana?

How often are flights from Chicago to Punta Cana delayed?

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

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

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

How many flights depart from Chicago Midway Airport to Punta Cana on average per day?

How many flights depart from Chicago Midway Airport to Punta Cana on average per week?

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

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

Southwest Flights From Chicago Midway Airport to Punta Cana

Traveling to a place near Punta Cana?

Why use momondo?

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

Fly your favorite airline to Punta Cana

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Punta Cana

List of cabin classes available on flights landing in Punta Cana. Availability may vary depending on flight origin and airline.

Popular cities in the Dominican Republic

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Chicago Midway Airport

According to popular flight searches on momondo this year

Complete your trip to Punta Cana

Explore popular destinations other users love

According to popular flight searches on momondo this year