HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Dominican Republic

$154+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(Kiwi.com)

One-way from

$154
(Kiwi.com)

Popular in

March

Cheapest in

April

Average price

$658

Good round-trip deal

$806 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. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/25. 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 5/51:19 pmMDW - PUJ
1 stop21h 25mMultiple Airlines
Thu 5/812:42 pmPUJ - MDW
1 stop24h 42mMultiple Airlines
Deal found 3/25$332
This Delta deal was found by Cheapflights users on 3/25. 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.
Sun 4/206:04 amMDW - PUJ
1 stop6h 11mDelta
Thu 4/242:40 pmPUJ - MDW
1 stop8h 42mDelta
Deal found 3/25$335
This Delta deal was found by Cheapflights users on 3/24. 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.
Tue 5/66:04 amMDW - SDQ
2 stops11h 19mDelta
Tue 5/137:00 amSDQ - MDW
2 stops12h 45mDelta
Deal found 3/24$411
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Fri 5/912:15 pmMDW - SDQ
1 stop21h 48mFrontier
Fri 5/168:00 amSDQ - MDW
2 stops26h 33mFrontier
Deal found 3/25$417
This Frontier deal was found by Cheapflights users on 3/26. 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.
Mon 5/269:12 pmMDW - PUJ
1 stop10h 35mFrontier
Sat 5/3112:25 pmPUJ - MDW
1 stop8h 30mFrontier
Deal found 3/26$421
This Delta deal was found by Cheapflights users on 3/25. 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 5/96:00 amMDW - STI
2 stops17h 14mDelta
Fri 5/166:11 amSTI - MDW
2 stops13h 34mDelta
Deal found 3/25$478
This Southwest deal was found by Cheapflights users on 3/25. 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.
Mon 5/125:45 amMDW - PUJ
1 stop8h 00mSouthwest
Sat 5/172:50 pmPUJ - MDW
Nonstop5h 05mSouthwest
Deal found 3/25$523
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Tue 4/14:40 pmMDW - SDQ
2 stops21h 59mMultiple Airlines
Sun 4/62:32 pmSDQ - MDW
1 stop22h 56mMultiple Airlines
Deal found 3/25$534

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 March 26, 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 5/5

1:19 pm-11:44 am

1 stop21h 25m

Punta Cana

Thu 5/8

12:42 pm-12:24 pm

1 stop24h 42m

$332

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 4/20

6:04 am-1:15 pm

1 stop6h 11m

Punta Cana

Thu 4/24

2:40 pm-10:22 pm

1 stop8h 42m

$335

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 5/6

6:04 am-6:23 pm

2 stops11h 19m

Santo Domingo Las Americas

Tue 5/13

7:00 am-6:45 pm

2 stops12h 45m

$411

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 5/9

12:15 pm-11:03 am

1 stop21h 48m

Santo Domingo Las Americas

Fri 5/16

8:00 am-9:33 am

2 stops26h 33m

$417

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 5/26

9:12 pm-8:47 am

1 stop10h 35m

Punta Cana

Sat 5/31

12:25 pm-7:55 pm

1 stop8h 30m

$421

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 5/9

6:00 am-12:14 am

2 stops17h 14m

Santiago de los Caballeros

Fri 5/16

6:11 am-6:45 pm

2 stops13h 34m

$478

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 5/12

5:45 am-2:45 pm

1 stop8h 00m

Punta Cana

Sat 5/17

2:50 pm-6:55 pm

Nonstop5h 05m

$523

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 5/21

9:59 pm-8:30 pm

3 stops21h 31m

Santo Domingo Las Americas

Sun 5/25

7:01 am-4:50 pm

2 stops34h 49m

$1,031

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 4/15

4:40 pm-11:44 am

1 stop18h 04m

$154

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/9

6:00 am-1:22 pm

1 stop6h 22m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 19 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 March is currently the most expensive (average of $599). 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 March 26, 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 March 26, 2025.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Southwest, Delta and Air Transat. 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
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
7,891 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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.
Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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.
LATAM Airlines
7.5
Good
1,749 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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
2,785 reviews
Southwest
8.1
Very good
4,274 reviews

Crew

8.6

Boarding

8.2

Overall

8.1

Food

7.1

Comfort

8.1

Entertainment

7.6

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 Delta. According to our data, you can fly for as low as $156. Users have also found prices from $196 and $300 on Frontier and Southwest, 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 $778. On average you can expect to pay $856. 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 March is currently the most expensive (average of $599). 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
Midway to Montego Bay flights
O'Hare Intl to Oranjestad 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 Willemstad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
O'Hare Intl to Christiansted flights
Midway to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Ponce flights
Midway to Santo Domingo flights
Midway to Providenciales flights
Midway to George Town flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. John's flights
Midway to Kingston flights
Midway to Simpson Bay flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Castries flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to St. George's flights
O'Hare Intl to Road Town flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Havana flights
O'Hare Intl to The Valley flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Georgetown flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Gustavia flights
Midway to Castries 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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$496FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$838FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$671Average$875FlexibilityNo 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.