Dominican Republic

$132+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Feb 27 — Mar 61
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Frontier)

One-way from

$132
(Booking.com)

Popular in

March

Cheapest in

April

Average price

$506

Good round-trip deal

$665 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
From Chicago Midway to Dominican Republic
One-way flight from Chicago Midway to Dominican Republic
High demand for flights, 1% potential price rise
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in February 2025
Price to beat on a round-trip flight from Chicago Midway to Dominican Republic.

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 February 22, 2025.

This Frontier deal was found by Cheapflights users on 2/21. 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.
Sat 5/246:44 pmMDW - PUJ
2 stops13h 07mFrontier
Mon 6/23:05 pmPUJ - MDW
1 stop9h 50mFrontier
Deal found 2/21$306
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/154:40 pmMDW - PUJ
1 stop18h 04mMultiple Airlines
Thu 5/153:07 pmPUJ - MDW
1 stop9h 32mMultiple Airlines
Deal found 2/20$322
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.
Tue 4/156:04 amMDW - PUJ
1 stop7h 26mDelta
Tue 4/223:55 pmPUJ - MDW
1 stop7h 31mDelta
Deal found 2/20$345
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.
Sat 5/244:11 pmMDW - SDQ
2 stops17h 27mFrontier
Thu 5/2912:00 pmSDQ - MDW
2 stops12h 55mFrontier
Deal found 2/20$385
This Delta deal was found by Cheapflights users on 2/21. 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.
Sat 4/196:04 amMDW - SDQ
1 stop6h 14mDelta
Wed 4/232:43 pmSDQ - MDW
1 stop8h 43mDelta
Deal found 2/21$427
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/27:25 amMDW - SDQ
1 stop11h 35mMultiple Airlines
Mon 3/101:42 pmSDQ - MDW
2 stops26h 50mMultiple Airlines
Deal found 2/20$429
This Southwest deal was found by Cheapflights users on 2/21. 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 4/79:05 amMDW - PUJ
Nonstop4h 25mSouthwest
Wed 4/162:30 pmPUJ - MDW
1 stop8h 35mSouthwest
Deal found 2/21$504
This Kissandfly.com 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:00 amMDW - SDQ
2 stops16h 56mKLM
Sun 3/97:43 pmSDQ - MDW
2 stops23h 35mKLM
Deal found 2/19$782
This Delta deal was found by Cheapflights users on 2/21. 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 4/246:04 amMDW - STI
2 stops11h 37mDelta
Mon 4/288:06 pmSTI - MDW
2 stops16h 57mDelta
Deal found 2/21$1,290

Find flights from Midway to Dominican Republic within your budget

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 February 22, 2025.

Fly from

Midway

Fly to

Dominican Republic

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 5/22

9:12 pm-8:51 am

1 stop10h 39m

Punta Cana

Wed 6/4

3:05 pm-11:55 pm

1 stop9h 50m

$313

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 4/15

4:40 pm-11:44 am

1 stop18h 04m

Punta Cana

Thu 5/15

3:07 pm-11:39 pm

1 stop9h 32m

$322

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 4/15

6:04 am-2:30 pm

1 stop7h 26m

Punta Cana

Tue 4/22

3:55 pm-10:26 pm

1 stop7h 31m

$345

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 5/24

4:11 pm-10:38 am

2 stops17h 27m

Santo Domingo Las Americas

Thu 5/29

12:00 pm-11:55 pm

2 stops12h 55m

$385

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 4/19

6:04 am-1:18 pm

1 stop6h 14m

Santo Domingo Las Americas

Wed 4/23

2:43 pm-10:26 pm

1 stop8h 43m

$427

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 4/7

9:05 am-2:30 pm

Nonstop4h 25m

Punta Cana

Wed 4/16

2:30 pm-10:05 pm

1 stop8h 35m

$504

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 3/6

7:25 am-11:44 am

2 stops26h 19m

Santo Domingo Las Americas

Sat 3/8

10:00 am-3:13 pm

1 stop7h 13m

$508

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 3/6

6:00 am-12:56 am

2 stops16h 56m

Santo Domingo Las Americas

Sun 3/9

7:43 pm-6:18 pm

2 stops23h 35m

$782

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 4/24

6:04 am-6:41 pm

2 stops11h 37m

Santiago de los Caballeros

Mon 4/28

8:06 pm-12:03 pm

2 stops16h 57m

$1,290

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 5/1

6:30 pm-1:34 pm

1 stop18h 04m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 18 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.

Travel insights for flights from Midway to Dominican Republic

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

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 $623). 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 February 22, 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 February 22, 2025.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Southwest, Delta and KLM. 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.

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

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.

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

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.

8.0
Very good

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

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.

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

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.

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

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 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 Frontier. According to our data, you can fly for as low as $132. Users have also found prices from $161 and $201 on Delta and Southwest, respectively.

  • What are the most popular routes 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 $608. On average you can expect to pay $836. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $322.

  • 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 $623). 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.

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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$531FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$794FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$671Average$876FlexibilityNo 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.