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Dominican Republic

$121+ Cheap flights from Midway (MDW) to the Dominican Republic

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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheap flight deals from Midway to Dominican Republic

Keep the following information in mind while searching for Midway to Dominican Republic flight deals. Data was last updated junio 12, 2025.

Round-trip from

$335
(Delta)

One-way from

$121
(Southwest)

Popular in

March

Cheapest in

July

Average price

$517

Good round-trip deal

$580 or less
From Chicago Midway to Dominican Republic
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One-way flight from Chicago Midway to Dominican Republic
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago Midway to Dominican Republic.
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Find flight deals from Midway to Dominican Republic

Cheapest flights from Midway to Dominican Republic
Explore the most affordable flight options available from Midway to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
dom. 11/166:00 amMDW - PUJ
1 stop7h 20mDelta
mié. 11/193:50 pmPUJ - MDW
1 stop7h 54mDelta
Deal found 6/10$335
This Southwest deal was found by Cheapflights users on 6/12. 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.
lun. 7/219:55 amMDW - PUJ
Nonstop4h 30mSouthwest
jue. 7/244:05 pmPUJ - MDW
Nonstop4h 50mSouthwest
Deal found 6/12$344
This Priceline deal was found by Cheapflights users on 6/9. 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.
jue. 8/216:15 amMDW - PUJ
1 stop7h 08mFrontier
dom. 8/243:38 pmPUJ - MDW
1 stop8h 49mFrontier
Deal found 6/9$347
This Frontier deal was found by Cheapflights users on 6/12. 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.
mar. 6/2411:39 amMDW - SDQ
1 stop11h 40mFrontier
jue. 7/1011:50 amSDQ - MDW
1 stop9h 32mFrontier
Deal found 6/12$405
This Trip.com deal was found by Cheapflights users on 6/12. 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.
jue. 9/256:00 amMDW - SDQ
1 stop6h 47mDelta
dom. 9/283:12 pmSDQ - MDW
1 stop7h 32mDelta
Deal found 6/12$422
This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 8/11:11 pmMDW - PUJ
2 stops25h 44mMultiple Airlines
jue. 8/73:25 pmPUJ - MDW
2 stops21h 56mMultiple Airlines
Deal found 6/11$459
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
jue. 8/2811:03 amMDW - SDQ
2 stops14h 07mMultiple Airlines
lun. 9/17:30 amSDQ - MDW
1 stop8h 59mMultiple Airlines
Deal found 6/11$522
This Delta deal was found by Cheapflights users on 6/10. 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.
sáb. 11/229:30 amMDW - STI
2 stops13h 56mDelta
mar. 12/99:59 pmSTI - MDW
2 stops15h 56mDelta
Deal found 6/10$1,717

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Dominican Republic 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 junio 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.

Fly from

Midway

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 9/2

6:00 am-2:34 pm

1 stop7h 34m

Punta Cana

mié. 9/24

2:42 pm-9:44 pm

1 stop8h 02m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 7/21

9:55 am-3:25 pm

Nonstop4h 30m

Punta Cana

jue. 7/24

4:05 pm-7:55 pm

Nonstop4h 50m

$344

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

jue. 8/21

6:15 am-2:23 pm

1 stop7h 08m

Punta Cana

dom. 8/24

3:38 pm-11:27 pm

1 stop8h 49m

$347

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

mar. 6/24

11:39 am-12:19 am

1 stop11h 40m

Santo Domingo Las Americas

jue. 7/10

11:50 am-8:22 pm

1 stop9h 32m

$405

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

vie. 8/1

1:11 pm-3:55 pm

2 stops25h 44m

Punta Cana

jue. 8/7

3:25 pm-12:21 pm

2 stops21h 56m

$459

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

sáb. 9/6

6:00 am-1:38 pm

1 stop6h 38m

Santo Domingo Las Americas

sáb. 9/13

6:10 am-6:36 pm

2 stops13h 26m

$464

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

jue. 8/28

11:03 am-2:10 am

2 stops14h 07m

Santo Domingo Las Americas

lun. 9/1

7:30 am-3:29 pm

1 stop8h 59m

$522

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

sáb. 11/22

9:30 am-1:26 am

2 stops13h 56m

Santiago de los Caballeros

mar. 12/9

9:59 pm-11:55 am

2 stops15h 56m

$1,717

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

sáb. 7/12

8:55 am-2:25 pm

Nonstop4h 30m

$121

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

jue. 8/21

6:15 am-2:23 pm

1 stop7h 08m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 17 results
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Best time to book a flight from Midway to Dominican Republic

Have a flexible travel schedule? Discover the best time to fly to Dominican Republic from Midway 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 Chicago Midway Airport to the Dominican Republic

What is the cheapest month to book a flight from Chicago Midway Airport to Dominican Republic?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $443). Flying from Chicago Midway Airport to Dominican Republic in March is currently the most expensive (average of $596). 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.

What is the cheapest time of day to fly from MDW to DO?

Find hourly flight availability from Midway to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Dominican Republic as you normally would.

Rainfall in Dominican Republic by month

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

In terms of precipitation, rainfall in Dominican Republic ranges from 2.1 - 6.0 inches per month. October is typically the wettest month, when rainfall can reach 6.0 in. February is typically the driest time to visit Dominican Republic when rainfall is around 2.1 in.

Temperature in Dominican Republic by month

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

If weather is an important factor for your trip to Dominican Republic, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. 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 Dominican Republic. Reviews last updated junio 12, 2025.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Southwest, Delta and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Midway to Dominican Republic. 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 Chicago Midway Airport to Dominican Republic one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $121. Users have also found prices from $154 and $156 on Frontier and Delta, respectively.

  • What are the most popular routes from Chicago Midway Airport to Dominican Republic?

    While some choose either Chicago Midway - Santo Domingo Las Americas or Chicago Midway - Santiago de los Caballeros, Chicago Midway - Punta Cana is the most popular route from Chicago Midway Airport to Dominican Republic.

  • What are the cheapest flights from Chicago Midway Airport to Dominican Republic?

    The cheapest flight price from Chicago Midway Airport to Dominican Republic is $415. On average you can expect to pay $620. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $260.

  • Can I find deals for flights from Midway to Dominican Republic that include hotel bookings?

    Yes. In addition to deals on Midway to Dominican Republic flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Dominican Republic?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Dominican Republic.

  • Can I find deals for business class flights from Midway to Dominican Republic?

    Yes. Cheapflights offers flight deals from Midway to Dominican Republic 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 Chicago Midway Airport to Dominican Republic?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dominican Republic (average of $443). Flying from Chicago Midway Airport to Dominican Republic in March is currently the most expensive (average of $596). 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

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Alternative routes for Midway to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
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O'Hare Intl to Castries flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Nassau flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Santo Domingo flights
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O'Hare Intl to George Town flights
O'Hare Intl to Bridgetown flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Christiansted flights
Midway to Nassau flights
O'Hare Intl to Kingston flights
Midway to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to St. John's flights
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O'Hare Intl to Port of Spain flights
O'Hare Intl to St. George's flights
O'Hare Intl to Road Town flights
Midway to George Town flights
O'Hare Intl to Castries flights
Midway to Simpson Bay flights
O'Hare Intl to Havana flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Aguadilla flights
Midway to Castries flights
O'Hare Intl to The Valley flights
Midway to Kingston flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Port Royal flights

Top 3 airlines flying from Midway to Dominican Republic

Discover the top 3 airlines that operate flights from Midway to Dominican Republic. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$370Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$646FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$742FlexibilityNo cancel feeOn-time63%

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