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Dominican Republic

$116+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$374
(Delta)

One-way from

$116
(Southwest)

Popular in

March

Cheapest in

May

Average price

$479

Good round-trip deal

$558 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
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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. 2% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 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 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 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.
Mon 8/116:00 amMDW - PUJ
1 stop6h 17mDelta
Fri 8/151:10 pmPUJ - MDW
1 stop9h 37mDelta
Deal found 4/30$335
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.
Mon 6/99:12 pmMDW - PUJ
2 stops14h 43mMultiple Airlines
Thu 6/1210:06 amPUJ - MDW
1 stop11h 11mMultiple Airlines
Deal found 4/30$394
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/58:55 amMDW - PUJ
Nonstop4h 30mSouthwest
Sat 7/123:40 pmPUJ - MDW
1 stop8h 50mSouthwest
Deal found 4/30$410
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.
Fri 5/239:12 pmMDW - PUJ
1 stop12h 38mFrontier
Sun 6/110:17 amPUJ - MDW
1 stop13h 15mFrontier
Deal found 4/30$421
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 5/2910:25 amMDW - SDQ
2 stops13h 09mDelta
Thu 6/57:00 amSDQ - MDW
2 stops12h 45mDelta
Deal found 4/30$421
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/286:40 pmMDW - SDQ
1 stop16h 09mFrontier
Sun 8/311:50 amSDQ - MDW
2 stops47h 50mFrontier
Deal found 4/30$448
This Delta deal was found by Cheapflights users on 4/28. 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 5/29:52 amMDW - STI
2 stops13h 35mDelta
Fri 5/96:11 amSTI - MDW
2 stops16h 17mDelta
Deal found 4/28$452
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/149:12 pmMDW - SDQ
1 stop27h 58mMultiple Airlines
Fri 7/187:30 amSDQ - MDW
1 stop13h 52mMultiple Airlines
Deal found 4/29$549

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 May 1, 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

Mon 8/11

6:00 am-1:17 pm

1 stop6h 17m

Punta Cana

Fri 8/15

1:10 pm-9:47 pm

1 stop9h 37m

$335

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 6/9

9:12 pm-12:55 pm

2 stops14h 43m

Punta Cana

Thu 6/12

10:06 am-8:17 pm

1 stop11h 11m

$394

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/5

8:55 am-2:25 pm

Nonstop4h 30m

Punta Cana

Sat 7/12

3:40 pm-11:30 pm

1 stop8h 50m

$410

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/23

9:12 pm-10:50 am

1 stop12h 38m

Punta Cana

Sun 6/1

10:17 am-10:32 pm

1 stop13h 15m

$421

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 5/29

10:25 am-12:34 am

2 stops13h 09m

Santo Domingo Las Americas

Thu 6/5

7:00 am-6:45 pm

2 stops12h 45m

$421

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 7/28

6:40 pm-11:49 am

1 stop16h 09m

Santo Domingo Las Americas

Sun 8/3

11:50 am-10:40 am

2 stops47h 50m

$448

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Wed 5/28

9:20 am-12:14 am

2 stops13h 54m

Santiago de los Caballeros

Wed 6/4

6:11 am-5:45 pm

2 stops12h 34m

$481

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 7/14

9:12 pm-2:10 am

1 stop27h 58m

Santo Domingo Las Americas

Fri 7/18

7:30 am-8:22 pm

1 stop13h 52m

$549

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/5

8:55 am-2:25 pm

Nonstop4h 30m

$116

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 5/28

2:53 pm-11:01 am

1 stop19h 08m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 16 results
1
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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 June is currently the most expensive (average of $598). 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 May 1, 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 May 1, 2025.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Southwest, Delta and WestJet. 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
4,294 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Entertainment

7.6

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Entertainment

7.6

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
4,294 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Entertainment

7.6

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
4,294 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Entertainment

7.6

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
4,294 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Entertainment

7.6

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 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 $116. Users have also found prices from $156 and $177 on Delta and Frontier, 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 $409. On average you can expect to pay $657. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $335.

  • 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 June is currently the most expensive (average of $598). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island 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
O'Hare Intl to Christiansted flights
O'Hare Intl to George Town flights
Midway to Oranjestad flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Saint Thomas Island flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Kingston flights
Midway to Nassau flights
Midway to Santiago de los Caballeros flights
Midway to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to Ponce flights
O'Hare Intl to St. John's flights
O'Hare Intl to Castries flights
O'Hare Intl to Road Town flights
Midway to George Town flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gustavia flights
O'Hare Intl to The Valley flights
O'Hare Intl to Havana flights
O'Hare Intl to Port of Spain flights
Midway to Kingston flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Freeport flights
O'Hare Intl to St. George's flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Port Royal flights
O'Hare Intl to Gregory Town flights
Midway to Castries flights
O'Hare Intl to Aguadilla flights
Midway to Simpson Bay 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$252Average$527FlexibilityNo cancel feeOn-time62%
DeltaCheapest$340Average$838FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$671Average$868FlexibilityNo cancel feeOn-time63%

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