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Dominican Republic

$129+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap 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 November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$309
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$545

Good round-trip deal

$789 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
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From Chicago Midway to Dominican Republic
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One-way flight from Chicago Midway to Dominican Republic
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Highest demand for flights based on searches. 4% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Chicago Midway to Dominican Republic.
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Find 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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sat 12/62:59 pmMDW - PUJ
1 stop25h 39mMultiple Airlines
Sat 12/134:14 pmPUJ - MDW
1 stop27h 58mMultiple Airlines
Deal found 11/6$309
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/42:16 pmMDW - PUJ
1 stop27h 38mMultiple Airlines
Thu 12/119:38 amPUJ - MDW
1 stop14h 15mMultiple Airlines
Deal found 11/5$321
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sat 12/62:59 pmMDW - SDQ
1 stop28h 46mMultiple Airlines
Sat 12/133:35 pmSDQ - MDW
1 stop8h 55mMultiple Airlines
Deal found 11/6$323
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/128:42 pmMDW - PUJ
1 stop16h 14mFrontier
Fri 12/193:39 pmPUJ - MDW
2 stops25h 49mFrontier
Deal found 11/5$329
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/128:42 pmMDW - PUJ
1 stop16h 14mMultiple Airlines
Fri 12/191:01 pmPUJ - MDW
1 stop22h 18mMultiple Airlines
Deal found 11/4$330
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Thu 11/275:30 pmMDW - PUJ
1 stop24h 55mMultiple Airlines
Thu 12/49:38 amPUJ - MDW
1 stop14h 15mMultiple Airlines
Deal found 11/6$331
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/58:42 pmMDW - PUJ
1 stop16h 14mMultiple Airlines
Fri 12/121:10 pmPUJ - MDW
1 stop11h 29mMultiple Airlines
Deal found 11/6$333
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/318:15 amMDW - PUJ
1 stop24h 12mMultiple Airlines
Wed 1/76:08 pmPUJ - MDW
2 stops31h 17mMultiple Airlines
Deal found 11/5$336
This Delta deal was found by Cheapflights users on 11/6. 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.
Thu 11/139:34 amMDW - SDQ
2 stops14h 02mDelta
Mon 11/176:45 amSDQ - MDW
2 stops13h 23mDelta
Deal found 11/6$444
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/15:47 pmMDW - SDQ
2 stops19h 43mMultiple Airlines
Sat 2/2810:56 amSDQ - MDW
1 stop8h 15mMultiple Airlines
Deal found 11/5$467
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Tue 11/256:20 amMDW - SDQ
1 stop8h 06mMultiple Airlines
Wed 11/2610:19 amSDQ - MDW
1 stop8h 38mMultiple Airlines
Deal found 11/3$469
This Delta deal was found by Cheapflights users on 11/6. 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.
Sat 12/61:14 pmMDW - SDQ
2 stops10h 34mDelta
Sat 12/136:35 amSDQ - MDW
2 stops13h 31mDelta
Deal found 11/6$473

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 November 6, 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

Tue 12/9

6:00 am-2:25 pm

1 stop6h 25m

Punta Cana

Tue 12/16

5:04 pm-11:47 pm

1 stop8h 43m

$338

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/31

8:15 am-2:35 pm

Nonstop4h 20m

Punta Cana

Sat 2/7

3:35 pm-10:10 pm

1 stop8h 35m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/12

6:45 am-4:41 pm

1 stop7h 56m

Punta Cana

Sat 1/17

3:45 pm-10:09 pm

1 stop8h 24m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/19

6:00 am-3:30 pm

1 stop7h 30m

Punta Cana

Sun 1/25

4:55 pm-10:26 pm

1 stop7h 31m

$367

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 1/23

6:00 am-2:20 pm

1 stop6h 20m

Punta Cana

Wed 1/28

4:55 pm-10:26 pm

1 stop7h 31m

$367

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/27

5:00 am-2:30 pm

1 stop7h 30m

Punta Cana

Tue 2/3

2:40 pm-9:00 pm

1 stop8h 20m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/24

5:10 am-2:00 pm

1 stop6h 50m

Punta Cana

Sat 1/31

3:35 pm-10:10 pm

1 stop8h 35m

$408

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/25

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Tue 1/27

7:31 am-10:26 pm

2 stops16h 55m

$434

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 2/3

6:17 pm-1:08 pm

2 stops16h 51m

Santo Domingo Las Americas

Tue 2/10

7:31 am-5:55 pm

2 stops12h 24m

$434

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 11/13

9:34 am-1:36 am

2 stops14h 02m

Santo Domingo Las Americas

Mon 11/17

6:45 am-6:08 pm

2 stops13h 23m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 38 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $194). 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 November 6, 2025.

It’s typically best to fly out from Chicago Midway Airport to Dominican Republic in the evening. Doing so could potentially save you 54% on the flight price compared to flying in the morning, which is usually more expensive.

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 November 6, 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
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,116 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 4h 20m. Chicago Midway Airport and Dominican Republic are separated by a distance of 1967 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Dominican Republic one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $141. Users have also found prices from $148 and $208 on Southwest and Delta, respectively.

  • 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 $617. On average you can expect to pay $919. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $309.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $194). 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
Midway to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to St. John's flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Bridgetown flights
Midway to George Town flights
Midway to Simpson Bay flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
O'Hare Intl to Road Town flights
O'Hare Intl to Kingston flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Ponce flights
Midway to Santo Domingo flights
O'Hare Intl to The Valley flights
O'Hare Intl to Kralendijk flights
Midway to Castries flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to St. George's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Freeport flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Castries flights
O'Hare Intl to Havana flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Fort-de-France flights
Midway to St. John's flights
O'Hare Intl to Pointe-à-Pitre flights
Midway to Kingston 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$406Average$762FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%

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