HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
avr. 22 — avr. 291
mar. 4/22
mar. 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Dominican Republic with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 avril 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$335
(Delta)

One-way from

$116
(Southwest)

Popular in

March

Cheapest in

May

Average price

$495

Good round-trip deal

$649 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
Search Deals
From Chicago Midway to Dominican Republic
Search Deals
One-way flight from Chicago Midway to Dominican Republic
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Dominican Republic.
Search Deals

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 avril 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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.
sam. 5/36:04 amMDW - PUJ
1 stop8h 28mDelta
mar. 5/612:55 pmPUJ - MDW
1 stop10h 27mDelta
Deal found 4/17$335
This Southwest deal was found by Cheapflights users on 4/17. 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.
ven. 7/49:55 amMDW - PUJ
Nonstop4h 30mSouthwest
mer. 7/93:45 pmPUJ - MDW
Nonstop4h 50mSouthwest
Deal found 4/17$375
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
dim. 6/89:12 pmMDW - PUJ
1 stop13h 35mMultiple Airlines
sam. 6/143:55 pmPUJ - MDW
1 stop17h 50mMultiple Airlines
Deal found 4/16$400
This Delta deal was found by Cheapflights users on 4/16. 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.
sam. 5/3110:25 amMDW - SDQ
2 stops12h 54mDelta
sam. 6/77:05 amSDQ - MDW
2 stops10h 16mDelta
Deal found 4/16$411
This Frontier deal was found by Cheapflights users on 4/16. 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.
lun. 5/269:12 pmMDW - PUJ
1 stop12h 38mFrontier
ven. 5/3012:25 pmPUJ - MDW
1 stop8h 30mFrontier
Deal found 4/16$421
This Mytrip deal was found by Cheapflights users on 4/17. 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.
dim. 6/14:06 pmMDW - SDQ
1 stop15h 56mFrontier
dim. 6/89:53 amSDQ - MDW
1 stop11h 24mFrontier
Deal found 4/17$445
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
ven. 6/139:12 pmMDW - SDQ
1 stop28h 09mMultiple Airlines
ven. 6/209:53 pmSDQ - MDW
2 stops25h 35mMultiple Airlines
Deal found 4/16$548
This Delta deal was found by Cheapflights users on 4/16. 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.
lun. 5/59:52 amMDW - STI
2 stops13h 35mDelta
ven. 5/96:11 amSTI - MDW
2 stops16h 17mDelta
Deal found 4/16$577

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 avril 17, 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

sam. 5/3

6:04 am-3:32 pm

1 stop8h 28m

Punta Cana

mar. 5/6

12:55 pm-10:22 pm

1 stop10h 27m

$335

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

ven. 7/4

9:55 am-3:25 pm

Nonstop4h 30m

Punta Cana

mer. 7/9

3:45 pm-7:35 pm

Nonstop4h 50m

$375

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dim. 6/8

9:12 pm-11:47 am

1 stop13h 35m

Punta Cana

sam. 6/14

3:55 pm-8:45 am

1 stop17h 50m

$400

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

sam. 5/31

10:25 am-12:19 am

2 stops12h 54m

Santo Domingo Las Americas

sam. 6/7

7:05 am-4:21 pm

2 stops10h 16m

$411

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 5/26

9:12 pm-10:50 am

1 stop12h 38m

Punta Cana

ven. 5/30

12:25 pm-7:55 pm

1 stop8h 30m

$421

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

dim. 6/1

4:06 pm-9:02 am

1 stop15h 56m

Santo Domingo Las Americas

dim. 6/8

9:53 am-8:17 pm

1 stop11h 24m

$445

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

ven. 6/13

9:12 pm-2:21 am

1 stop28h 09m

Santo Domingo Las Americas

ven. 6/20

9:53 pm-10:28 pm

2 stops25h 35m

$548

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

lun. 5/5

9:52 am-12:27 am

2 stops13h 35m

Santiago de los Caballeros

ven. 5/9

6:11 am-9:28 pm

2 stops16h 17m

$577

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

ven. 7/4

9:55 am-3:25 pm

Nonstop4h 30m

$116

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 7/15

6:00 am-1:17 pm

1 stop6h 17m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 16 results
1
2

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 avril 17, 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 avril 17, 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
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,809 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $193 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 $518. On average you can expect to pay $781. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $345.

  • 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
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
Midway to Oranjestad flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Puerto Plata flights
Midway to Nassau flights
O'Hare Intl to Providenciales flights
Midway to Saint Thomas Island flights
O'Hare Intl to Kingston flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
Midway to Santo Domingo flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to St. John's flights
O'Hare Intl to Road Town flights
O'Hare Intl to Ponce flights
Midway to George Town flights
O'Hare Intl to Port of Spain flights
Midway to Simpson Bay flights
O'Hare Intl to Havana flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gregory Town flights
Midway to Kingston flights
O'Hare Intl to Freeport flights
O'Hare Intl to Culebra flights
O'Hare Intl to Basseterre flights
O'Hare Intl to The Valley flights
O'Hare Intl to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Georgetown flights
Midway to Castries flights
O'Hare Intl to Pointe-à-Pitre 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 avril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$252Average$531FlexibilityNo cancel feeOn-time62%
DeltaCheapest$340Average$838FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$671Average$869FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.