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Dominican Republic

$141+ Cheap flights from Midway (MDW) to the Dominican Republic

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Midway to Dominican Republic

Cheapest flights from Midway to Dominican Republic
Explore the most affordable flight options available from Midway to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:12 amMDW - PUJ
1 stop6h 57mFrontier
Thu 1/154:07 pmPUJ - MDW
2 stops19h 02mFrontier
Deal found 12/22$350
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:08 pmMDW - PUJ
1 stop16h 20mDelta
Wed 12/316:03 pmPUJ - MDW
1 stop17h 02mDelta
Deal found 12/21$362
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - PUJ
1 stop20h 59mMultiple Airlines
Fri 1/161:01 pmPUJ - MDW
1 stop7h 53mMultiple Airlines
Deal found 12/22$430
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amMDW - PUJ
1 stop7h 21mDelta
Thu 1/154:55 pmPUJ - MDW
1 stop7h 12mDelta
Deal found 12/22$431
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:59 pmMDW - PUJ
1 stop18h 36mDelta
Mon 12/292:06 pmPUJ - MDW
1 stop10h 16mDelta
Deal found 12/22$440
This Delta deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amMDW - PUJ
1 stop7h 21mDelta
Sat 1/173:45 pmPUJ - MDW
1 stop8h 22mDelta
Deal found 12/22$456
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:59 pmMDW - PUJ
1 stop18h 36mDelta
Wed 12/316:03 pmPUJ - MDW
1 stop17h 02mDelta
Deal found 12/21$463
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:08 pmMDW - PUJ
1 stop16h 20mDelta
Wed 12/316:03 pmPUJ - MDW
1 stop17h 02mDelta
Deal found 12/21$470
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - SDQ
1 stop8h 34mFrontier
Tue 12/3012:35 pmSDQ - MDW
1 stop11h 23mFrontier
Deal found 12/22$503
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - SDQ
1 stop8h 34mFrontier
Wed 12/316:04 pmSDQ - MDW
2 stops30h 08mFrontier
Deal found 12/22$504
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:15 amMDW - SDQ
1 stop8h 34mMultiple Airlines
Tue 12/3010:41 amSDQ - MDW
2 stops29h 56mMultiple Airlines
Deal found 12/22$518
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - SDQ
1 stop7h 12mFrontier
Mon 12/292:53 pmSDQ - MDW
1 stop9h 05mFrontier
Deal found 12/21$533

Find flight deals from Midway to Dominican Republic

Keep the following information in mind while searching for Midway to Dominican Republic flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$141
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$608

Good round-trip deal

$381 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
Search Deals
From Chicago Midway to Dominican Republic
Search Deals
One-way flight from Chicago Midway to Dominican Republic
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Dominican Republic.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Dominican Republic that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.

Fly from

Midway

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/17

8:22 am-4:36 pm

2 stops30h 14m

Punta Cana

Sat 1/24

4:11 pm-11:45 am

1 stop21h 34m

$361

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 2/18

3:42 pm-10:31 pm

1 stop8h 49m

$390

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 1/21

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 1/28

7:30 am-5:55 pm

2 stops12h 25m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/25

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Tue 2/3

7:30 am-10:22 pm

2 stops16h 52m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 2/7

10:53 am-12:30 am

2 stops11h 37m

Santo Domingo Las Americas

Wed 2/18

3:42 pm-10:31 pm

1 stop8h 49m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 2/16

9:22 pm-11:56 am

1 stop12h 34m

Santo Domingo Las Americas

Thu 2/19

12:31 pm-2:26 pm

1 stop27h 55m

$397

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 3/2

9:22 pm-11:56 am

1 stop12h 34m

Santo Domingo Las Americas

Mon 3/9

10:56 am-8:53 pm

1 stop10h 57m

$397

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/18

6:45 am-3:30 pm

1 stop6h 45m

Punta Cana

Thu 1/22

3:45 pm-10:22 pm

1 stop8h 37m

$402

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 2/8

6:00 am-2:10 pm

1 stop6h 10m

Punta Cana

Wed 2/11

4:55 pm-10:22 pm

1 stop7h 27m

$402

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/27

6:00 am-2:20 pm

1 stop6h 20m

Punta Cana

Tue 2/3

4:55 pm-10:22 pm

1 stop7h 27m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 48 results
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Best time to book a flight from Midway to Dominican Republic

Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to the Dominican Republic

What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $266). Flying from Chicago Midway Airport to Dominican Republic in August is currently the most expensive (average of $762). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to DO?

Find hourly flight availability from Midway to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s typically best to fly out from Chicago Midway Airport to Dominican Republic in the evening. Doing so could potentially save you 53% on the flight price compared to flying in the morning, which is usually more expensive.

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

About 22% of weekly flights between Chicago and Dominican Republic have experienced delays in the past year, with the average delay time being 112 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

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

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, Southwest have had the lowest number of delays on this route, with just 21% of flights being delayed.

Reviews of airlines servicing Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Dominican Republic. Reviews last updated December 23, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to the Dominican Republic, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,013 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,074 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Dominican Republic. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Dominican Republic?

    Departing from Chicago Midway Airport to Dominican Republic will take you 6h 21m. Chicago Midway Airport and Dominican Republic are separated by a distance of 1932 mi.

  • What are the most popular routes from Chicago Midway Airport to Dominican Republic?

    While some choose either Chicago Midway - Santo Domingo Las Americas or Chicago Midway - Santiago de los Caballeros, Chicago Midway - Punta Cana is the most popular route from Chicago Midway Airport to Dominican Republic.

  • What are the cheapest flights from Chicago Midway Airport to Dominican Republic?

    The cheapest flight price from Chicago Midway Airport to Dominican Republic is $348. On average you can expect to pay $412. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $346.

  • Can I find deals for flights from Midway to Dominican Republic that include hotel bookings?

    Yes. In addition to deals on Midway to Dominican Republic flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Dominican Republic?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Dominican Republic.

  • Can I find deals for business class flights from Midway to Dominican Republic?

    Yes. Cheapflights offers flight deals from Midway to Dominican Republic by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $266). Flying from Chicago Midway Airport to Dominican Republic in August is currently the most expensive (average of $762). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
O'Hare Intl to Willemstad flights
Midway to Montego Bay flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Ponce flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
Midway to George Town flights
O'Hare Intl to Kingston flights
O'Hare Intl to St. John's flights
O'Hare Intl to Port of Spain flights
Midway to Santo Domingo flights
Midway to Simpson Bay flights
O'Hare Intl to Road Town flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Freeport flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Havana flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Georgetown flights
Midway to Kingston flights
O'Hare Intl to The Valley flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Castries flights
Midway to St. John's flights
Midway to Castries flights
O'Hare Intl to Pointe-à-Pitre flights

Top 3 airlines flying from Midway to Dominican Republic

Discover the top 3 airlines that operate flights from Midway to Dominican Republic. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$406Average$648FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$421Average$659FlexibilityNo cancel feeOn-time63%

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