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$154+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PUJ — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$299
(Frontier)

One-way from

$154
(Mytrip)

Popular in

June

Cheapest in

May

Average price

$459

Good one-way deal

$308 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. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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.
Thu 5/13:07 pmPUJ - MDW
1 stop9h 32mFrontier
Mon 5/56:15 amMDW - PUJ
2 stops10h 23mFrontier
Deal found 2/20$299
This Frontier deal was found by Cheapflights users on 2/20. 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.
Thu 5/88:00 amSDQ - MDW
2 stops16h 39mFrontier
Mon 5/126:15 amMDW - SDQ
2 stops16h 40mFrontier
Deal found 2/20$352
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/22:43 pmSDQ - MDW
1 stop8h 43mDelta
Tue 5/66:04 amMDW - SDQ
2 stops11h 15mDelta
Deal found 2/20$450
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/12:40 pmPUJ - MDW
1 stop8h 46mDelta
Mon 5/56:04 amMDW - PUJ
1 stop6h 11mDelta
Deal found 2/20$506
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:50 pmPUJ - MDW
1 stop8h 35mSouthwest
Mon 8/255:00 amMDW - PUJ
1 stop8h 05mSouthwest
Deal found 2/20$683
This LATAM Airlines deal was found by Cheapflights users on 2/20. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/202:45 amPUJ - MDW
2 stops31h 33mLATAM Airlines
Mon 8/256:50 pmMDW - PUJ
2 stops19h 25mLATAM Airlines
Deal found 2/20$2,468
This WestJet deal was found by Cheapflights users on 2/19. 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.
Mon 9/111:45 amPUJ - MDW
2 stops22h 33mWestJet
Thu 9/41:05 pmMDW - PUJ
2 stops20h 44mWestJet
Deal found 2/19$3,646

Find flights from Dominican Republic to Midway within your budget

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 20, 2025.

Fly from

Dominican Republic

Fly to

Midway

Route

Depart

Return

Price

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/1

3:07 pm-11:39 pm

1 stop9h 32m

Chicago Midway

Mon 5/5

6:15 am-5:38 pm

2 stops10h 23m

$299

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 5/8

8:00 am-11:39 pm

2 stops16h 39m

Chicago Midway

Mon 5/12

6:15 am-11:55 pm

2 stops16h 40m

$352

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 5/2

2:43 pm-10:26 pm

1 stop8h 43m

Chicago Midway

Tue 5/6

6:04 am-6:19 pm

2 stops11h 15m

$450

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Thu 5/1

2:40 pm-10:26 pm

1 stop8h 46m

Chicago Midway

Mon 5/5

6:04 am-1:15 pm

1 stop6h 11m

$506

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 5/21

5:35 pm-11:56 am

2 stops19h 21m

Chicago Midway

Sat 5/24

3:45 pm-5:35 pm

2 stops24h 50m

$3,732

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 8/19

12:25 pm-1:02 pm

2 stops25h 37m

Chicago Midway

Tue 8/26

1:05 pm-1:43 pm

2 stops23h 38m

$3,921

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 4/21

2:46 pm-9:18 am

1 stop19h 32m

$154

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 5/13

4:03 pm-11:26 am

2 stops20h 23m

$163

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 4/23

3:55 pm-10:26 pm

1 stop7h 31m

$193

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 5/4

8:00 am-10:40 pm

2 stops15h 40m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Dominican Republic to Midway

Get recent, data-driven insights about flights from Dominican Republic to Midway including ideal travel times, pricing trends, and more.

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 20, 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Air Transat 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
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Air Transat
7.8
Good
380 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $154. Users have also found prices from $193 and $292 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 $543, our data shows the cheapest flight currently is $223. When looking at the most popular route, (Santo Domingo Las Americas - Chicago Midway), you can expect to pay $450 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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