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$186+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$428
(Kiwi.com)

One-way from

$186
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$313

Good one-way deal

$367 or less
Provider with most accurate pricing for Punta Cana-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Punta Cana-Chicago (CHI) flights.
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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. 11% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/82:47 pmPUJ - MDW
1 stop7h 41mDelta
Sun 5/116:00 amMDW - PUJ
1 stop6h 22mDelta
Deal found 4/30$341
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/1910:13 amSDQ - MDW
1 stop11h 04mMultiple Airlines
Sun 6/229:12 pmMDW - SDQ
1 stop27h 32mMultiple Airlines
Deal found 5/1$428
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:34 pmPUJ - MDW
1 stop8h 43mMultiple Airlines
Sun 6/229:12 pmMDW - PUJ
2 stops15h 58mMultiple Airlines
Deal found 4/30$430
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:00 amSDQ - MDW
2 stops12h 36mDelta
Thu 10/309:30 amMDW - SDQ
2 stops12h 59mDelta
Deal found 4/29$438
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/510:23 amSDQ - MDW
1 stop10h 54mFrontier
Thu 6/122:55 pmMDW - SDQ
1 stop8h 24mFrontier
Deal found 4/30$473
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/229:52 amPUJ - MDW
1 stop11h 25mFrontier
Sun 5/256:10 amMDW - PUJ
1 stop7h 00mFrontier
Deal found 5/1$475
This Southwest deal was found by Cheapflights users on 5/1. 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.
Fri 5/91:40 pmPUJ - MDW
2 stops19h 35mSouthwest
Sun 5/116:40 amMDW - PUJ
1 stop6h 50mSouthwest
Deal found 5/1$582
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:45 amPUJ - MDW
2 stops31h 00mWestJet
Sun 6/19:20 amMDW - PUJ
2 stops24h 28mWestJet
Deal found 5/1$3,609

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 May 1, 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 6/19

10:13 am-8:17 pm

1 stop11h 04m

Chicago Midway

Sun 6/22

9:12 pm-1:44 am

1 stop27h 32m

$428

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/19

12:34 pm-8:17 pm

1 stop8h 43m

Chicago Midway

Sun 6/22

9:12 pm-2:10 pm

2 stops15h 58m

$430

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

7:00 am-6:36 pm

2 stops12h 36m

Chicago Midway

Thu 10/30

9:30 am-11:29 pm

2 stops12h 59m

$438

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 6/5

10:23 am-8:17 pm

1 stop10h 54m

Chicago Midway

Thu 6/12

2:55 pm-12:19 am

1 stop8h 24m

$473

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/22

9:52 am-8:17 pm

1 stop11h 25m

Chicago Midway

Sun 5/25

6:10 am-2:10 pm

1 stop7h 00m

$475

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

2:42 pm-9:47 pm

1 stop8h 05m

Chicago Midway

Tue 8/26

6:00 am-1:17 pm

1 stop6h 17m

$647

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sun 5/11

2:30 pm-11:40 pm

1 stop10h 10m

Chicago Midway

Tue 5/13

5:55 am-1:30 pm

1 stop6h 35m

$654

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/29

11:45 am-5:45 pm

2 stops31h 00m

Chicago Midway

Sun 6/1

9:20 am-10:48 am

2 stops24h 28m

$3,609

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 6/7

12:42 pm-7:25 pm

1 stop7h 43m

$186

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 6/12

10:06 am-8:17 pm

1 stop11h 11m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 16 results
1
2

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 May 1, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta and WestJet from Dominican Republic to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,293 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,826 reviews
Southwest
8.0
Very good
4,293 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,293 reviews

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $195. Users have also found prices from $222 and $251 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 $487, our data shows the cheapest flight currently is $367. When looking at the most popular route, (Santo Domingo Las Americas - Chicago Midway), you can expect to pay $438 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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