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Dominican Republic

$160+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$343
(Southwest)

One-way from

$160
(Delta)

Popular in

March

Cheapest in

July

Average price

$482

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. 3% potential increase in price ($17 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 July 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 9/15:10 amMDW - PUJ
1 stop7h 55mSouthwest
Fri 9/53:05 pmPUJ - MDW
1 stop7h 30mSouthwest
Deal found 7/29$343
This Delta deal was found by Cheapflights users on 7/28. 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 11/176:00 amMDW - PUJ
1 stop6h 23mDelta
Wed 11/194:55 pmPUJ - MDW
2 stops21h 37mDelta
Deal found 7/28$347
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/99:12 pmMDW - PUJ
2 stops43h 03mFrontier
Tue 8/123:25 pmPUJ - MDW
1 stop20h 15mFrontier
Deal found 7/28$352
This Frontier deal was found by Cheapflights users on 7/28. 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.
Tue 8/511:39 amMDW - SDQ
1 stop11h 53mFrontier
Tue 8/121:48 amSDQ - MDW
1 stop9h 52mFrontier
Deal found 7/28$375
This Delta deal was found by Cheapflights users on 7/28. 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 9/136:00 amMDW - SDQ
1 stop6h 40mDelta
Sat 9/203:06 pmSDQ - MDW
1 stop7h 04mDelta
Deal found 7/28$427
This Delta deal was found by Cheapflights users on 7/30. 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 9/1311:00 amMDW - STI
2 stops12h 34mDelta
Sat 9/206:11 amSTI - MDW
2 stops15h 59mDelta
Deal found 7/30$427
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:15 pmMDW - STI
2 stops16h 50mMultiple Airlines
Mon 9/2212:10 pmSTI - MDW
2 stops12h 10mMultiple Airlines
Deal found 7/28$538

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 July 30, 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

Mon 9/1

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Fri 9/5

3:05 pm-9:35 pm

1 stop7h 30m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/17

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Wed 11/19

4:55 pm-12:32 pm

2 stops21h 37m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/9

9:12 pm-5:15 pm

2 stops43h 03m

Punta Cana

Tue 8/12

3:25 pm-10:40 am

1 stop20h 15m

$352

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 8/5

11:39 am-12:32 am

1 stop11h 53m

Santo Domingo Las Americas

Tue 8/12

1:48 am-10:40 am

1 stop9h 52m

$375

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/13

6:00 am-1:40 pm

1 stop6h 40m

Santo Domingo Las Americas

Sat 9/20

3:06 pm-9:10 pm

1 stop7h 04m

$427

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Sat 9/13

11:00 am-12:34 am

2 stops12h 34m

Santiago de los Caballeros

Sat 9/20

6:11 am-9:10 pm

2 stops15h 59m

$427

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 9/19

5:15 pm-11:05 am

2 stops16h 50m

Santiago de los Caballeros

Mon 9/22

12:10 pm-11:20 pm

2 stops12h 10m

$538

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 8/8

9:40 am-7:25 am

2 stops20h 45m

Santo Domingo Las Americas

Thu 8/14

5:05 pm-6:17 pm

3 stops26h 12m

$793

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 10/28

6:00 am-1:24 pm

1 stop6h 24m

$160

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 8/30

6:10 am-2:19 pm

1 stop7h 09m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 15 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 $594). 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 July 30, 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 July 30, 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
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $160. Users have also found prices from $161 and $185 on Frontier and Southwest, 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 $343.

  • 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 $594). 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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Providenciales flights
Midway to Oranjestad flights
O'Hare Intl to George Town flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
Midway to Santo Domingo flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
O'Hare Intl to St. John's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to St. George's flights
Midway to Simpson Bay flights
Midway to George Town flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Ponce flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Road Town flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Castries flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Havana flights
Midway to Castries flights
O'Hare Intl to Freeport flights
Midway to Kingston flights
O'Hare Intl to The Valley flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Port Royal 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$703FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%

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