How often are flights from Chicago to the Dominican Republic delayed?

Historically, on average around 39% of flights between Chicago and Dominican Republic have experienced a delay on any given week. The average delay length over the past 12 months has been 90 minutes.

Which airline has the best punctuality record on Chicago to the Dominican Republic flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 39% of their flights experiencing any sort of delay.

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

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

What is the cheapest airline that flies from Chicago Midway to Dominican Republic?

Delta and Southwest are the most popular carriers operating from Chicago Midway to Dominican Republic

What is the most punctual flight time for Chicago to the Dominican Republic 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.

How many operators does momondo search for flights from Chicago Midway Airport to Dominican Republic?

As of October 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Dominican Republic.

How old do you have to be to fly from Chicago Midway Airport to Dominican Republic?

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 Dominican Republic.

What documentation or ID do you need to fly to Dominican Republic?

The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$169 Cheap Flights from Chicago Midway Airport to Dominican Republic in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to the Dominican Republic

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:40 am - 3:15 pmMDW Chicago Midway-PUJ Punta Cana

4h 35mnonstop

3:35 pm - 9:40 pmPUJ Punta Cana-MDW Chicago Midway

8h 05m1 stop Orlando

$376Southwest

Sat, Nov 28 - Sat, Dec 5

5:20 am - 2:40 pmMDW Chicago Midway-PUJ Punta Cana

7h 20m1 stop Orlando

4:10 pm - 11:15 pmPUJ Punta Cana-MDW Chicago Midway

9h 05m1 stop Baltimore/Washington

$380Southwest

Tue, Nov 17 - Tue, Nov 24

6:00 am - 4:42 pmMDW Chicago Midway-PUJ Punta Cana

8h 42m1 stop Atlanta Hartsfield-Jackson

4:20 pm - 8:49 amPUJ Punta Cana-MDW Chicago Midway

18h 29m1 stop Minneapolis St Paul

$380Delta

Sun, Jan 31 - Mon, Feb 8

6:00 am - 4:42 pmMDW Chicago Midway-PUJ Punta Cana

8h 42m1 stop Atlanta Hartsfield-Jackson

4:20 pm - 8:49 amPUJ Punta Cana-MDW Chicago Midway

18h 29m1 stop Minneapolis St Paul

$380Delta

Fri, Jan 22 - Mon, Jan 25

5:25 am - 4:00 pmMDW Chicago Midway-PUJ Punta Cana

8h 35m1 stop Baltimore/Washington

3:35 pm - 9:40 pmPUJ Punta Cana-MDW Chicago Midway

8h 05m1 stop Orlando

$380Southwest

Sat, Nov 28 - Sat, Dec 5

5:25 am - 3:50 pmMDW Chicago Midway-PUJ Punta Cana

8h 25m1 stop Orlando

2:40 pm - 9:15 pmPUJ Punta Cana-MDW Chicago Midway

8h 35m1 stop Orlando

$380Southwest

Mon, Nov 30 - Fri, Dec 4

6:00 am - 4:42 pmMDW Chicago Midway-PUJ Punta Cana

8h 42m1 stop Atlanta Hartsfield-Jackson

4:20 pm - 8:49 amPUJ Punta Cana-MDW Chicago Midway

18h 29m1 stop Minneapolis St Paul

$380Delta

Mon, Feb 8 - Wed, Feb 17

3:50 pm - 1:41 pmMDW Chicago Midway-PUJ Punta Cana

19h 51m2 stops Atlanta Hartsfield-Jackson San Juan Luis Munoz Marin Intl

7:19 pm - 2:55 pmPUJ Punta Cana-MDW Chicago Midway

21h 36m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson

$470Frontier

Thu, Dec 3 - Thu, Dec 10

12:28 pm - 1:41 pmMDW Chicago Midway-PUJ Punta Cana

23h 13m2 stops Atlanta Hartsfield-Jackson San Juan Luis Munoz Marin Intl

7:30 pm - 2:55 pmPUJ Punta Cana-MDW Chicago Midway

21h 25m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson

$483Frontier

Wed, Dec 2 - Wed, Dec 9

3:50 pm - 1:41 pmMDW Chicago Midway-PUJ Punta Cana

19h 51m2 stops Atlanta Hartsfield-Jackson San Juan Luis Munoz Marin Intl

7:19 pm - 2:55 pmPUJ Punta Cana-MDW Chicago Midway

21h 36m2 stops San Juan Luis Munoz Marin Intl Atlanta Hartsfield-Jackson

$484Frontier

Thu, Dec 3 - Thu, Dec 10

Cheap last minute flights

Enter your travel dates to find the best prices.

5:45 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 00m1 stop Orlando

2:45 pm - 9:25 pmPUJ Punta Cana-MDW Chicago Midway

7h 40m1 stop Baltimore/Washington

$500Southwest

Tue, Oct 20 - Tue, Oct 27

8:55 pm - 1:00 pmMDW Chicago Midway-PUJ Punta Cana

15h 05m2 stops Baltimore/Washington Orlando

2:45 pm - 10:00 pmPUJ Punta Cana-MDW Chicago Midway

8h 15m1 stop Baltimore/Washington

$510Southwest

Fri, Oct 16 - Fri, Oct 23

7:00 pm - 1:50 pmMDW Chicago Midway-PUJ Punta Cana

17h 50m2 stops Orlando Baltimore/Washington

2:45 pm - 10:00 pmPUJ Punta Cana-MDW Chicago Midway

8h 15m1 stop Baltimore/Washington

$510Southwest

Sat, Oct 17 - Fri, Oct 23

5:00 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 45m1 stop Orlando

2:45 pm - 9:25 pmPUJ Punta Cana-MDW Chicago Midway

7h 40m1 stop Baltimore/Washington

$510Southwest

Mon, Oct 19 - Tue, Oct 20

5:00 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 45m1 stop Orlando

2:45 pm - 8:25 amPUJ Punta Cana-MDW Chicago Midway

18h 40m2 stops Baltimore/Washington Orlando

$515Southwest

Mon, Oct 19 - Tue, Oct 20

6:04 am - 1:32 pmMDW Chicago Midway-SDQ Santo Domingo Las Americas

6h 28m1 stop Atlanta Hartsfield-Jackson

2:57 pm - 10:33 pmSDQ Santo Domingo Las Americas-MDW Chicago Midway

8h 36m1 stop Atlanta Hartsfield-Jackson

$520Delta

Tue, Oct 20 - Wed, Oct 28

5:45 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 00m1 stop Orlando

2:45 pm - 9:25 pmPUJ Punta Cana-MDW Chicago Midway

7h 40m1 stop Baltimore/Washington

$525Southwest

Tue, Oct 20 - Tue, Oct 27

6:04 am - 1:30 pmMDW Chicago Midway-PUJ Punta Cana

6h 26m1 stop Atlanta Hartsfield-Jackson

4:05 pm - 10:33 pmPUJ Punta Cana-MDW Chicago Midway

7h 28m1 stop Atlanta Hartsfield-Jackson

$550Delta

Tue, Oct 20 - Tue, Oct 27

5:45 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 00m1 stop Orlando

2:45 pm - 8:25 amPUJ Punta Cana-MDW Chicago Midway

18h 40m2 stops Baltimore/Washington Orlando

$550Southwest

Tue, Oct 20 - Tue, Oct 27

5:45 am - 1:45 pmMDW Chicago Midway-PUJ Punta Cana

7h 00m1 stop Orlando

2:45 pm - 8:25 amPUJ Punta Cana-MDW Chicago Midway

18h 40m2 stops Baltimore/Washington Orlando

$570Southwest

Tue, Oct 20 - Tue, Oct 27

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Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets

Southwest

Nov 28

MDW8:40 amChicago Midway

4h 35m

PUJ3:15 pmPunta Cana

Dec 5

PUJ3:35 pmPunta Cana

8h 05m

1 stop

MDW9:40 pmChicago Midway

$376

Southwest

Oct 25

MDW5:10 amChicago Midway

8h 10m

1 stop

PUJ2:20 pmPunta Cana

Nov 1

PUJ2:40 pmPunta Cana

10h 25m

1 stop

MDW11:05 pmChicago Midway

$400

Southwest

Nov 28

MDW8:40 amChicago Midway

4h 35m

PUJ3:15 pmPunta Cana

Dec 5

PUJ3:35 pmPunta Cana

8h 05m

1 stop

MDW9:40 pmChicago Midway

$436

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets

Delta

Jan 30

MDW6:00 amChicago Midway

7h 30m

1 stop

PUJ3:30 pmPunta Cana

Feb 6

PUJ4:55 pmPunta Cana

7h 15m

1 stop

MDW10:10 pmChicago Midway

$380

Delta

Jan 30

MDW5:35 pmChicago Midway

17h 55m

2 stops

PUJ1:30 pmPunta Cana

Feb 3

PUJ5:45 pmPunta Cana

17h 00m

2 stops

MDW8:45 amChicago Midway

$385

Delta

Feb 1

MDW6:00 amChicago Midway

7h 30m

1 stop

PUJ3:30 pmPunta Cana

Feb 8

PUJ4:20 pmPunta Cana

18h 29m

1 stop

MDW8:49 amChicago Midway

$400

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Sat 11/28

8:40 am-3:15 pm

Nonstop4h 35m

Punta Cana

Sat 12/5

3:35 pm-9:40 pm

1 stop8h 05m

$376

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Tue 11/17

5:20 am-2:40 pm

1 stop7h 20m

Punta Cana

Tue 11/24

4:10 pm-11:15 pm

1 stop9h 05m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Sun 1/31

6:00 am-4:42 pm

1 stop8h 42m

Punta Cana

Mon 2/8

4:20 pm-8:49 am

1 stop18h 29m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Fri 1/22

6:00 am-4:42 pm

1 stop8h 42m

Punta Cana

Mon 1/25

4:20 pm-8:49 am

1 stop18h 29m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Sat 11/28

5:25 am-4:00 pm

1 stop8h 35m

Punta Cana

Sat 12/5

3:35 pm-9:40 pm

1 stop8h 05m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Mon 11/30

5:25 am-3:50 pm

1 stop8h 25m

Punta Cana

Fri 12/4

2:40 pm-9:15 pm

1 stop8h 35m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Mon 2/8

6:00 am-4:42 pm

1 stop8h 42m

Punta Cana

Wed 2/17

4:20 pm-8:49 am

1 stop18h 29m

$380

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Thu 12/3

3:50 pm-1:41 pm

2 stops19h 51m

Punta Cana

Thu 12/10

7:19 pm-2:55 pm

2 stops21h 36m

$470

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Wed 12/2

12:28 pm-1:41 pm

2 stops23h 13m

Punta Cana

Wed 12/9

7:30 pm-2:55 pm

2 stops21h 25m

$483

ChicagoPunta Cana

MDW Chicago Midway - PUJ Punta Cana

MDWPUJ

Chicago Midway

Thu 12/3

3:50 pm-1:41 pm

2 stops19h 51m

Punta Cana

Thu 12/10

7:19 pm-2:55 pm

2 stops21h 36m

$484

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 Dominican Republic

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 Dominican Republic?

In general, December is the cheapest month to fly from Chicago Midway Airport to Dominican Republic. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you are unable to visit Dominican Republic during the month of December, then departing from Chicago Midway Airport during the month November is also very affordable. Most momondo users find prices during this month for around $0.

What is the cheapest day to depart on your flight to Dominican Republic?

The cheapest day to depart on your flight to Dominican Republic is on a Saturday when prices can be found for as low as $628. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Dominican Republic on a Friday will generally be more expensive and average around $855. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest Chicago Midway to Dominican Republic flight route?

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

What cabin class options are available on Chicago Midway Airport to Dominican Republic flights?

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

Cheap Chicago Midway Airport to Dominican Republic flight deals and tips

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

Best Price Found	$169
Fastest flight time	4h 25m
Direct flights	Every day
Airports in Dominican Republic	16 airports

The best one-way flight to Dominican Republic from Chicago Midway Airport in the past 72 hours is $169. The best round-trip flight deal from Chicago Midway Airport to Dominican Republic found on momondo in the last 72 hours is $376.

The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 25m

Direct flights go from Chicago Midway Airport to Dominican Republic every day.

There are 16 airports in Dominican Republic. From Chicago Midway Airport there are direct flights to Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to the Dominican Republic

When did momondo last update prices for flights from Chicago Midway Airport to Dominican Republic?
Prices for flights from Chicago Midway Airport to Dominican Republic are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to Dominican Republic?
As of October 2026, there are 2 operators available to choose from for flights from Chicago Midway Airport to Dominican Republic.
How old do you have to be to fly from Chicago Midway Airport to Dominican Republic?
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 Dominican Republic.
What documentation or ID do you need to fly to Dominican Republic?
The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Dominican Republic?
Based on momondo bookings for flights between Chicago Midway Airport and Dominican Republic, the leading plane model is Boeing 737, making up 24.14% of the total bookings. Other popular models include Boeing 737 MAX 8 with 20.69%, Boeing 737 MAX 9 with 10.34%, and Airbus A321neo with 10.34%.

Best airlines flying from Chicago Midway Airport to Dominican Republic

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dominican Republic with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $478	Free Cancellation	Rating 5.5 2,539 reviews		Search Frontier flights
Southwest	PriceFrom $511	Free Cancellation	Rating 7.9 4,214 reviews		Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dominican Republic?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Dominican Republic. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Dominican Republic with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Dominican Republic from Chicago with this policy.

How can momondo help me find flights from Chicago to Dominican Republic?

momondo provides multiple filters to help you find the best flight to Dominican Republic from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

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

An easier way to manage your Dominican Republic trip

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Complete your trip

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Popular cities in the Dominican Republic

Flights to Punta Canafrom $262

Flights to Santo Domingofrom $256

Flights to Santiago de los Caballerosfrom $305

Flights to Puerto Platafrom $420

Flights to La Romanafrom $379

Flights to Naguafrom $616

Cheap flights from Chicago Midway Airport to the Dominican Republic from $169

Find the cheapest flights from Chicago Midway Airport to the Dominican Republic

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Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets

momondo Fare Finder

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

See travel insights to the Dominican Republic from

How to get the cheapest flight ticket from Chicago Midway Airport to Dominican Republic

What is the cheapest month to fly to Dominican Republic?

What is the cheapest day to depart on your flight to Dominican Republic?

What is the cheapest Chicago Midway to Dominican Republic flight route?

What cabin class options are available on Chicago Midway Airport to Dominican Republic flights?

What is the cheapest airline that flies from Chicago Midway to Dominican Republic?

How often are flights from Chicago to the Dominican Republic delayed?

What is the most punctual flight time for Chicago to the Dominican Republic flights?

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

Which airline has the best punctuality record on Chicago to the Dominican Republic flights?

Cheap Chicago Midway Airport to Dominican Republic flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Dominican Republic

Frequently asked questions about flying from Chicago Midway Airport to the Dominican Republic

Best airlines flying from Chicago Midway Airport to Dominican Republic

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dominican Republic with momondo

Why use momondo?

An easier way to manage your Dominican Republic 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

Popular cities in the Dominican Republic

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

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Dominican Republic flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to the Dominican Republic

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

Cabin classes currently available on flights to the Dominican Republic

List of cabin classes available on flights landing in the Dominican Republic. Availability may vary depending on flight origin and airline.

Complete your trip to the Dominican Republic

Explore popular destinations other users love

According to popular flight searches on momondo this year