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$175+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$341
(Kiwi.com)

One-way from

$175
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$367
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. 15% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

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 10/99:38 amPUJ - MDW
1 stop26h 49mMultiple Airlines
Mon 10/205:28 pmMDW - PUJ
1 stop17h 14mMultiple Airlines
Deal found 9/15$341
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:35 pmSDQ - MDW
1 stop20h 52mMultiple Airlines
Mon 10/134:24 pmMDW - SDQ
1 stop28h 21mMultiple Airlines
Deal found 9/13$368
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.
Wed 10/81:40 pmPUJ - MDW
1 stop9h 55mSouthwest
Mon 10/135:00 amMDW - PUJ
1 stop8h 30mSouthwest
Deal found 9/14$386
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.
Fri 10/102:45 pmPUJ - MDW
2 stops10h 10mSouthwest
Mon 10/137:05 amMDW - PUJ
1 stop6h 25mSouthwest
Deal found 9/14$391
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/254:00 pmPUJ - MDW
2 stops9h 50mSouthwest
Mon 12/15:20 amMDW - PUJ
1 stop7h 40mSouthwest
Deal found 9/15$393
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.
Fri 11/144:00 pmPUJ - MDW
2 stops17h 30mSouthwest
Sun 11/305:30 amMDW - PUJ
1 stop7h 40mSouthwest
Deal found 9/14$398
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.
Thu 11/136:10 amSDQ - MDW
1 stop19h 45mMultiple Airlines
Mon 11/176:15 amMDW - SDQ
2 stops9h 35mMultiple Airlines
Deal found 9/13$402
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.
Fri 12/262:45 pmPUJ - MDW
1 stop10h 20mSouthwest
Sat 1/108:15 amMDW - PUJ
Nonstop4h 20mSouthwest
Deal found 9/14$421
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.
Thu 10/306:10 amSDQ - MDW
1 stop18h 15mMultiple Airlines
Thu 11/66:25 amMDW - SDQ
2 stops9h 25mMultiple Airlines
Deal found 9/14$424
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.
Sat 12/273:45 pmPUJ - MDW
1 stop10h 30mSouthwest
Sun 1/45:25 amMDW - PUJ
2 stops7h 35mSouthwest
Deal found 9/14$430
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:19 pmSDQ - MDW
1 stop7h 44mFrontier
Mon 11/36:20 amMDW - SDQ
2 stops9h 01mFrontier
Deal found 9/14$439
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.
Thu 9/181:20 pmSDQ - MDW
1 stop20h 33mMultiple Airlines
Thu 9/254:56 pmMDW - SDQ
2 stops22h 33mMultiple Airlines
Deal found 9/14$453

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 September 16, 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

Thu 10/9

9:38 am-11:27 am

1 stop26h 49m

Chicago Midway

Mon 10/20

5:28 pm-11:42 am

1 stop17h 14m

$341

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:35 pm-11:27 am

1 stop20h 52m

Chicago Midway

Mon 10/13

4:24 pm-9:45 pm

1 stop28h 21m

$368

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 10/10

2:45 pm-11:25 pm

1 stop9h 40m

Chicago Midway

Mon 10/13

7:05 am-2:30 pm

1 stop6h 25m

$386

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 11/25

4:00 pm-9:55 pm

1 stop7h 55m

Chicago Midway

Mon 12/1

5:20 am-3:00 pm

1 stop7h 40m

$393

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 11/14

2:40 pm-11:00 pm

1 stop10h 20m

Chicago Midway

Sun 11/30

5:30 am-3:10 pm

1 stop7h 40m

$393

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/19

5:11 pm-8:54 am

1 stop17h 43m

Chicago Midway

Sun 2/22

6:45 pm-2:30 pm

1 stop17h 45m

$396

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 12/26

2:45 pm-11:05 pm

1 stop10h 20m

Chicago Midway

Sat 1/10

8:15 am-2:35 pm

Nonstop4h 20m

$421

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 12/27

4:55 pm-11:25 pm

1 stop8h 30m

Chicago Midway

Sun 1/4

5:35 am-3:10 pm

1 stop7h 35m

$425

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Mon 11/3

6:20 am-5:21 pm

2 stops9h 01m

$439

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/16

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Wed 10/22

6:00 am-1:41 pm

1 stop6h 41m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 30 results
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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
No data available for this route at this time. Please check back soon.

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.

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

    Departing from Dominican Republic to Chicago Midway Airport will take you 7h 44m. The distance between Dominican Republic and Chicago Midway Airport is about 1932 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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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