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Dominican Republic

$154+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$334
(Kiwi.com)

One-way from

$154
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$477

Good one-way deal

$126 or less
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. 8% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way 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 September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/2412:18 pmMDW - PUJ
1 stop27h 13mMultiple Airlines
Sat 11/19:38 amPUJ - MDW
1 stop12h 44mMultiple Airlines
Deal found 9/14$334
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/2712:17 pmMDW - PUJ
1 stop8h 12mMultiple Airlines
Sat 11/19:38 amPUJ - MDW
1 stop12h 44mMultiple Airlines
Deal found 9/12$335
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1511:36 amMDW - PUJ
1 stop29h 14mMultiple Airlines
Sat 11/229:38 amPUJ - MDW
1 stop9h 19mMultiple Airlines
Deal found 9/12$353
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:25 amMDW - PUJ
1 stop7h 45mSouthwest
Tue 10/211:40 pmPUJ - MDW
1 stop9h 55mSouthwest
Deal found 9/14$357
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:25 amMDW - PUJ
1 stop6h 55mSouthwest
Thu 10/302:45 pmPUJ - MDW
2 stops9h 30mSouthwest
Deal found 9/14$361
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 11/166:00 amMDW - PUJ
1 stop8h 18mDelta
Thu 11/202:38 pmPUJ - MDW
1 stop10h 54mDelta
Deal found 9/15$363
This Delta deal was found by Cheapflights users on 9/14. 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 12/316:00 amMDW - PUJ
1 stop7h 26mDelta
Thu 1/85:11 pmPUJ - MDW
1 stop17h 43mDelta
Deal found 9/14$365
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:35 pmMDW - PUJ
2 stops17h 35mSouthwest
Wed 11/122:40 pmPUJ - MDW
1 stop8h 25mSouthwest
Deal found 9/13$368
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/98:25 amMDW - SDQ
2 stops31h 04mMultiple Airlines
Mon 10/1310:19 amSDQ - MDW
1 stop14h 27mMultiple Airlines
Deal found 9/15$368
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/285:56 pmMDW - SDQ
1 stop21h 30mMultiple Airlines
Tue 11/46:10 amSDQ - MDW
1 stop19h 45mMultiple Airlines
Deal found 9/13$373
This Delta deal was found by Cheapflights users on 9/15. 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 10/1811:10 amMDW - SDQ
2 stops12h 17mDelta
Sat 10/256:05 amSDQ - MDW
2 stops13h 20mDelta
Deal found 9/15$379
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:15 amMDW - PUJ
1 stop7h 07mFrontier
Sat 10/253:32 pmPUJ - MDW
1 stop8h 15mFrontier
Deal found 9/14$383

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 September 15, 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

Sun 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

Thu 11/20

5:43 pm-11:32 pm

1 stop7h 49m

$357

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/26

6:25 am-2:20 pm

1 stop6h 55m

Punta Cana

Thu 10/30

2:45 pm-11:25 pm

1 stop9h 40m

$357

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/4

6:00 pm-12:30 pm

1 stop16h 30m

Punta Cana

Thu 1/8

5:11 pm-8:54 am

1 stop17h 43m

$365

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 10/9

8:25 am-4:29 pm

2 stops31h 04m

Santo Domingo Las Americas

Mon 10/13

10:19 am-11:46 pm

1 stop14h 27m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/18

5:25 pm-1:20 pm

2 stops17h 55m

Punta Cana

Thu 1/22

5:11 pm-8:54 am

1 stop17h 43m

$370

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 12/31

6:00 pm-3:26 pm

2 stops19h 26m

Punta Cana

Thu 1/8

5:11 pm-8:54 am

1 stop17h 43m

$370

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 10/28

5:56 pm-4:26 pm

1 stop21h 30m

Santo Domingo Las Americas

Tue 11/4

6:10 am-11:55 pm

1 stop19h 45m

$373

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 9/30

6:00 am-1:24 pm

1 stop6h 24m

Santo Domingo Las Americas

Sat 10/4

6:03 am-6:35 pm

2 stops13h 32m

$379

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 10/4

9:35 am-12:36 am

2 stops14h 01m

Santo Domingo Las Americas

Sat 10/11

6:05 am-6:25 pm

2 stops13h 20m

$379

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 10/18

10:35 am-12:27 am

2 stops12h 52m

Santo Domingo Las Americas

Sat 10/25

6:05 am-6:25 pm

2 stops13h 20m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 46 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $443). Flying from Chicago Midway Airport to Dominican Republic in June is currently the most expensive (average of $591). 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 September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Dominican Republic as you normally would.

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 September 15, 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
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

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 6h 55m. 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 Southwest. According to our data, you can fly for as low as $166. Users have also found prices from $176 and $203 on Delta and Frontier, 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 $126. On average you can expect to pay $146. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $334.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $443). Flying from Chicago Midway Airport to Dominican Republic in June is currently the most expensive (average of $591). 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 Montego Bay flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
Midway to Montego Bay 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
O'Hare Intl to Castries flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
Midway to Providenciales flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Kingston flights
O'Hare Intl to St. John's flights
O'Hare Intl to Puerto Plata flights
Midway to Simpson Bay flights
Midway to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Road Town flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Freeport flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Castries flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Kingstown flights
Midway to Kingston flights
O'Hare Intl to St. George's flights
O'Hare Intl to Havana flights
O'Hare Intl to Ponce flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Pointe-à-Pitre flights
Midway to St. John's flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to The Valley flights
O'Hare Intl to Gustavia 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$406Average$703FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$743FlexibilityNo cancel feeOn-time63%

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