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$156+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Delta deal was found by Cheapflights users on 2/3. 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 3/103:50 pm
PUJ
-
MDW
1 stop7h 41m
Delta
Tue 3/176:00 am
MDW
-
PUJ
1 stop8h 40m
Delta
Deal found 2/3$369
This eDestinos deal was found by Cheapflights users on 2/3. 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.
Tue 2/241:11 pm
SDQ
-
MDW
2 stops31h 56m
Frontier
Sat 2/286:25 am
MDW
-
SDQ
2 stops25h 14m
Frontier
Deal found 2/3$403
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/246:10 am
SDQ
-
MDW
2 stops14h 57m
Multiple Airlines
Sat 2/288:00 am
MDW
-
SDQ
1 stop23h 39m
Multiple Airlines
Deal found 2/3$444
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/266:10 am
SDQ
-
MDW
1 stop7h 52m
Multiple Airlines
Mon 3/309:42 pm
MDW
-
SDQ
1 stop23h 03m
Multiple Airlines
Deal found 2/3$453
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/196:10 am
SDQ
-
MDW
1 stop7h 52m
Multiple Airlines
Thu 3/267:30 am
MDW
-
SDQ
1 stop21h 01m
Multiple Airlines
Deal found 2/1$464
This Delta deal was found by Cheapflights users on 2/3. 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 2/263:42 pm
SDQ
-
MDW
1 stop8h 49m
Delta
Mon 3/29:34 am
MDW
-
SDQ
2 stops12h 58m
Delta
Deal found 2/3$477
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/203:42 pm
SDQ
-
MDW
1 stop8h 49m
Delta
Mon 2/236:00 am
MDW
-
SDQ
1 stop6h 17m
Delta
Deal found 2/2$489
This Delta deal was found by Cheapflights users on 2/3. 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.
Fri 4/172:37 pm
SDQ
-
MDW
1 stop8h 51m
Delta
Mon 4/206:00 am
MDW
-
SDQ
1 stop6h 12m
Delta
Deal found 2/3$529
This Southwest deal was found by Cheapflights users on 2/3. 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 3/102:35 pm
PUJ
-
MDW
Nonstop5h 05m
Southwest
Tue 3/176:00 am
MDW
-
PUJ
1 stop6h 35m
Southwest
Deal found 2/3$536
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/283:35 pm
SDQ
-
MDW
1 stop24h 21m
Multiple Airlines
Mon 3/309:42 pm
MDW
-
SDQ
1 stop23h 03m
Multiple Airlines
Deal found 2/3$537
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/203:30 pm
PUJ
-
MDW
1 stop7h 30m
Southwest
Mon 2/235:30 am
MDW
-
PUJ
1 stop7h 00m
Southwest
Deal found 2/2$554
This Priceline deal was found by Cheapflights users on 2/3. 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.
Fri 2/134:14 pm
PUJ
-
MDW
2 stops24h 41m
Frontier
Sun 2/156:15 am
MDW
-
PUJ
2 stops30h 49m
Frontier
Deal found 2/3$565

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$369
(Delta)

One-way from

$156
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$270

Good one-way deal

$464 or less
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 ($83 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 February 2026
Search Deals
Price to beat on a one-way flight from Dominican Republic to Chicago Midway.
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 February 4, 2026.
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

Tue 3/10

3:50 pm-10:31 pm

1 stop7h 41m

Chicago Midway

Tue 3/17

6:00 am-3:40 pm

1 stop8h 40m

$369

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 3/19

6:10 am-1:02 pm

1 stop7h 52m

Chicago Midway

Thu 3/26

7:30 am-5:31 am

1 stop21h 01m

$464

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/25

3:42 pm-10:31 pm

1 stop8h 49m

Chicago Midway

Wed 3/4

10:49 am-12:32 am

2 stops11h 43m

$477

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

9:34 am-12:32 am

2 stops12h 58m

$477

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/10

2:35 pm-6:40 pm

Nonstop5h 05m

Chicago Midway

Tue 3/17

6:00 am-1:35 pm

1 stop6h 35m

$536

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/20

3:30 pm-9:00 pm

1 stop7h 30m

Chicago Midway

Mon 2/23

5:30 am-2:30 pm

1 stop7h 00m

$554

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 2/13

3:30 pm-10:15 pm

1 stop8h 45m

Chicago Midway

Sun 2/15

5:30 am-2:30 pm

1 stop7h 00m

$671

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 2/24

3:50 pm-10:33 pm

1 stop8h 43m

Chicago Midway

Sun 3/1

6:00 am-4:41 pm

1 stop8h 41m

$797

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 2/26

4:30 pm-8:54 am

2 stops18h 24m

Chicago Midway

Sat 2/28

1:28 pm-6:20 am

2 stops38h 52m

$5,613

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Fri 3/6

4:15 pm-1:41 pm

2 stops23h 26m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 29 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 February 4, 2026.

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 05m. 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.

  • 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 $492, our data shows the cheapest flight currently is $266. When looking at the most popular route, (Santo Domingo Las Americas - Chicago Midway), you can expect to pay $419 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.

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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