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$166+ Cheap flights from the Dominican Republic to Midway (MDW)

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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Dominican Republic to Midway

Keep the following information in mind while searching for Dominican Republic to Midway flight deals. Data was last updated July 3, 2025.

Round-trip from

$369
(Southwest)

One-way from

$166
(Mytrip)

Popular in

June

Cheapest in

May

Average price

$482

Good one-way deal

$199 or less
From Dominican Republic to Chicago Midway
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One-way flight from Dominican Republic to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 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 Dominican Republic to Chicago Midway.
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Find flight deals from Dominican Republic to Midway

Cheapest flights from Dominican Republic to Midway
Explore the most affordable flight options available from Dominican Republic to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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.
Wed 8/132:50 pmPUJ - MDW
1 stop7h 50mSouthwest
Sun 8/175:35 amMDW - PUJ
1 stop7h 30mSouthwest
Deal found 7/1$369
This Delta deal was found by Cheapflights users on 7/1. 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 8/212:40 pmPUJ - MDW
1 stop8h 04mDelta
Sat 8/236:04 amMDW - PUJ
1 stop6h 11mDelta
Deal found 7/1$380
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Tue 8/123:25 pmPUJ - MDW
1 stop20h 15mFrontier
Sat 8/166:20 amMDW - PUJ
1 stop7h 14mFrontier
Deal found 7/2$403
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 9/202:12 pmSDQ - MDW
1 stop19h 41mMultiple Airlines
Fri 9/262:39 pmMDW - SDQ
2 stops10h 16mMultiple Airlines
Deal found 7/2$421
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Thu 7/1011:50 amSDQ - MDW
1 stop9h 32mFrontier
Sun 7/136:20 amMDW - SDQ
1 stop17h 08mFrontier
Deal found 7/1$437
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 7/1712:40 pmPUJ - MDW
1 stop8h 42mMultiple Airlines
Thu 7/249:12 pmMDW - PUJ
2 stops19h 03mMultiple Airlines
Deal found 7/1$439
This Delta deal was found by Cheapflights users on 7/1. 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 10/273:15 pmSDQ - MDW
1 stop7h 29mDelta
Thu 10/306:00 amMDW - SDQ
1 stop6h 53mDelta
Deal found 7/1$450

Cheapflights Fare Finder

Customize your flight search to find flights from Dominican Republic to Midway 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 3, 2025.
Use the filters below to find and compare flights from the Dominican Republic to Chicago Midway Airport that are best for you.

Fly from

Dominican Republic

Fly to

Midway

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 8/13

2:50 pm-9:40 pm

1 stop7h 50m

Chicago Midway

Sun 8/17

5:35 am-2:05 pm

1 stop7h 30m

$369

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 8/21

2:40 pm-9:44 pm

1 stop8h 04m

Chicago Midway

Sat 8/23

6:04 am-1:15 pm

1 stop6h 11m

$380

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/12

3:25 pm-10:40 am

1 stop20h 15m

Chicago Midway

Sat 8/16

6:20 am-2:34 pm

1 stop7h 14m

$403

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 9/20

2:12 pm-8:53 am

1 stop19h 41m

Chicago Midway

Fri 9/26

2:39 pm-1:55 am

2 stops10h 16m

$421

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 7/17

12:40 pm-8:22 pm

1 stop8h 42m

Chicago Midway

Thu 7/24

9:12 pm-5:15 pm

2 stops19h 03m

$439

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

3:15 pm-9:44 pm

1 stop7h 29m

Chicago Midway

Thu 10/30

9:30 am-11:29 pm

2 stops12h 59m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 7/29

1:48 am-10:40 am

1 stop9h 52m

Chicago Midway

Mon 8/4

6:40 pm-11:49 am

1 stop16h 09m

$451

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 9/20

3:55 pm-8:19 am

1 stop17h 24m

$166

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 10/18

3:22 pm-11:09 pm

1 stop8h 47m

$178

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 9/16

2:45 pm-9:36 pm

1 stop7h 51m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 14 results
1
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Best time to book a flight from Dominican Republic to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Dominican Republic 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 the Dominican Republic to Chicago Midway Airport

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

Find hourly flight availability from Dominican Republic to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

When flying from Dominican Republic to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier from the Dominican Republic to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Dominican Republic to Midway. 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 Dominican Republic to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $178. Users have also found prices from $192 and $197 on Delta and Southwest, respectively.

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

    While on average a flight from Dominican Republic to Chicago Midway Airport is generally $341, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Santo Domingo Las Americas - Chicago Midway), you can expect to pay $421 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Dominican Republic to Midway 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 Dominican Republic to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Dominican Republic to Chicago Midway Airport (average of $160). Flying from Dominican Republic to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near the Dominican Republic?

Book flights to the Dominican Republic if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Dominican Republic to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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