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$165+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/293:39 pmPUJ - MDW
2 stops48h 58mFrontier
Mon 1/58:15 amMDW - PUJ
1 stop28h 44mFrontier
Deal found 12/22$384
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/316:08 pmPUJ - MDW
2 stops30h 04mMultiple Airlines
Wed 1/73:01 pmMDW - PUJ
1 stop23h 30mMultiple Airlines
Deal found 12/22$410
This Mytrip deal was found by Cheapflights users on 12/22. 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 12/2511:37 amPUJ - MDW
1 stop12h 35mFrontier
Thu 1/16:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/22$427
This Expedia deal was found by Cheapflights users on 12/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:19 pmPUJ - MDW
1 stop27h 19mFrontier
Wed 12/316:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/21$431
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/3010:40 amPUJ - MDW
1 stop29h 57mMultiple Airlines
Tue 1/66:52 amMDW - PUJ
2 stops31h 58mMultiple Airlines
Deal found 12/22$433
This Frontier deal was found by Cheapflights users on 12/20. 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.
Sat 12/2711:37 amPUJ - MDW
1 stop12h 35mFrontier
Wed 12/316:12 amMDW - PUJ
1 stop6h 57mFrontier
Deal found 12/20$441
This Delta deal was found by Cheapflights users on 12/22. 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.
Tue 12/234:46 pmPUJ - MDW
1 stop7h 36mDelta
Tue 12/306:00 amMDW - PUJ
1 stop6h 13mDelta
Deal found 12/22$453
This Delta deal was found by Cheapflights users on 12/22. 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 12/294:46 pmPUJ - MDW
1 stop7h 36mDelta
Mon 1/56:45 amMDW - PUJ
1 stop7h 56mDelta
Deal found 12/22$462
This Southwest deal was found by Cheapflights users on 12/22. 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 12/234:00 pmPUJ - MDW
1 stop8h 25mSouthwest
Tue 12/305:45 amMDW - PUJ
1 stop7h 25mSouthwest
Deal found 12/22$486
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/233:35 pmSDQ - MDW
1 stop25h 02mMultiple Airlines
Tue 12/303:10 pmMDW - SDQ
1 stop10h 22mMultiple Airlines
Deal found 12/22$548
This Trip.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/3012:35 pmSDQ - MDW
1 stop11h 23mFrontier
Sun 1/46:00 amMDW - SDQ
1 stop7h 18mFrontier
Deal found 12/21$733
This Frontier deal was found by Cheapflights users on 12/22. 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 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Tue 12/303:10 pmMDW - SDQ
2 stops16h 16mFrontier
Deal found 12/22$786

Find 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 December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$165
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$397
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
Search Deals
From Dominican Republic to Chicago Midway
Search Deals
One-way flight from Dominican Republic to Chicago Midway
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 23, 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

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/19

12:31 pm-2:26 pm

1 stop27h 55m

Chicago Midway

Sat 2/28

8:00 am-9:39 am

1 stop23h 39m

$327

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/19

12:31 pm-2:26 pm

1 stop27h 55m

Chicago Midway

Sat 2/21

8:00 am-9:39 am

1 stop23h 39m

$327

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 3/30

8:25 pm-12:29 pm

2 stops17h 04m

Chicago Midway

Tue 4/7

6:25 am-11:53 pm

2 stops16h 28m

$476

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 1/23

4:55 pm-10:22 pm

1 stop7h 27m

Chicago Midway

Fri 1/30

6:00 am-2:20 pm

1 stop6h 20m

$476

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 5/9

12:55 pm-4:55 pm

Nonstop5h 00m

Chicago Midway

Sat 5/16

9:40 am-3:00 pm

Nonstop4h 20m

$481

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 1/17

10:27 am-8:03 am

2 stops23h 36m

Chicago Midway

Tue 2/17

6:00 am-11:26 am

2 stops51h 26m

$482

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 2/25

2:40 pm-9:00 pm

1 stop8h 20m

Chicago Midway

Wed 3/4

5:00 am-2:30 pm

1 stop7h 30m

$495

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/19

7:30 am-5:45 pm

2 stops12h 15m

Chicago Midway

Sat 2/28

6:00 am-3:30 pm

1 stop7h 30m

$504

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

7:30 am-5:37 pm

2 stops12h 07m

Chicago Midway

Mon 3/2

10:49 am-12:32 am

2 stops11h 43m

$504

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 4/28

1:10 pm-10:29 pm

1 stop10h 19m

Chicago Midway

Tue 5/5

6:30 am-2:48 pm

1 stop7h 18m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 34 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

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 December 23, 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.

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 5h. The distance between Dominican Republic and Chicago Midway Airport is about 1967 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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