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Dominican Republic

$112+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PUJ
Dec 26 — Jan 21
Thu 12/26
Thu 1/2
1 adult, Economy
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Cheap flight deals from Midway to Dominican Republic

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Dominican Republic (DO0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 21, 2024.

Round-trip from

$258
(Booking.com)

One-way from

$112
(Mytrip)
From Chicago Midway to Dominican Republic
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One-way 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 December 21, 2024.

This FlightHub deal was found by Cheapflights users on 12/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/272:35 pmMDW - PUJ
1 stop20h 14mFrontier
Mon 12/301:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 12/19$449
This Gotogate deal was found by Cheapflights users on 12/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/247:45 amMDW - SDQ
1 stop26h 38mFrontier
Thu 12/268:55 pmSDQ - MDW
1 stop13h 26mFrontier
Deal found 12/20$553
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/276:00 amMDW - SDQ
2 stops39h 37mMultiple Airlines
Tue 12/319:00 amSDQ - MDW
1 stop8h 13mMultiple Airlines
Deal found 12/19$644
This Southwest deal was found by Cheapflights users on 12/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:00 amMDW - PUJ
1 stop6h 45mSouthwest
Sat 12/284:55 pmPUJ - MDW
Nonstop5h 00mSouthwest
Deal found 12/20$723
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Fri 12/272:35 pmMDW - PUJ
1 stop20h 14mMultiple Airlines
Thu 1/21:06 pmPUJ - MDW
1 stop28h 00mMultiple Airlines
Deal found 12/20$885
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/236:00 amMDW - PUJ
1 stop8h 34mDelta
Fri 12/273:50 pmPUJ - MDW
1 stop8h 16mDelta
Deal found 12/21$1,077
This CheapOair deal was found by Cheapflights users on 12/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/265:52 pmMDW - STI
2 stops20h 00mFrontier
Thu 1/25:25 pmSTI - MDW
2 stops16h 56mFrontier
Deal found 12/20$1,124
This Delta deal was found by Cheapflights users on 12/20. 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.
Fri 12/276:00 amMDW - SDQ
1 stop6h 29mDelta
Tue 1/147:05 amSDQ - MDW
2 stops13h 09mDelta
Deal found 12/20$1,155
This KAYAK deal was found by Cheapflights users on 12/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/235:03 pmMDW - PUJ
2 stops20h 02mLATAM Airlines
Tue 12/242:45 amPUJ - MDW
2 stops21h 21mLATAM Airlines
Deal found 12/19$2,672
This WestJet deal was found by Cheapflights users on 12/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/225:04 pmMDW - PUJ
2 stops44h 50mWestJet
Sun 12/295:00 pmPUJ - MDW
2 stops31h 06mWestJet
Deal found 12/21$3,578
This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/266:00 amMDW - STI
2 stops16h 22mDelta
Wed 1/13:35 amSTI - MDW
2 stops16h 09mDelta
Deal found 12/20$5,164

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 December 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 2/27

4:13 pm-2:00 pm

1 stop19h 47m

Punta Cana

Mon 3/3

3:10 pm-7:32 am

1 stop18h 22m

$258

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/14

6:00 am-2:23 pm

1 stop6h 23m

Punta Cana

Thu 1/23

3:48 pm-10:20 pm

1 stop8h 32m

$363

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 2/21

7:15 pm-6:23 pm

2 stops45h 08m

Santiago de los Caballeros

Mon 3/3

7:43 pm-7:07 am

2 stops37h 24m

$368

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 4/2

12:40 pm-1:44 pm

1 stop24h 04m

Santo Domingo Las Americas

Sun 4/6

2:54 pm-12:08 pm

2 stops22h 14m

$443

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 1/24

6:00 am-1:57 pm

1 stop5h 57m

Santo Domingo Las Americas

Fri 1/31

3:22 pm-10:20 pm

1 stop8h 58m

$450

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/25

6:35 am-3:25 pm

1 stop6h 50m

Punta Cana

Sat 2/1

5:00 pm-8:00 pm

Nonstop5h 00m

$458

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/7

5:24 pm-3:55 pm

2 stops20h 31m

Punta Cana

Sat 1/11

12:21 pm-11:29 pm

1 stop13h 08m

$459

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 1/14

5:24 pm-3:54 pm

2 stops20h 30m

Santo Domingo Las Americas

Thu 1/16

9:00 am-3:13 pm

1 stop8h 13m

$519

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 2/3

9:33 am-1:33 am

2 stops14h 00m

Santiago de los Caballeros

Mon 2/10

6:35 am-6:11 pm

2 stops13h 36m

$551

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 1/14

10:19 am-3:54 pm

3 stops27h 35m

Punta Cana

Thu 1/23

5:00 pm-5:47 pm

2 stops26h 47m

$718

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 18 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.

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 $640). 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 December 21, 2024.

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 December 21, 2024.
Read through reviews of airlines operating flights from Chicago to Dominican Republic, such as Delta, Southwest 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
8.1
Very good
4,814 reviews

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,814 reviews
Southwest
8.1
Very good
4,814 reviews

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,597 reviews
Southwest
8.1
Very good
4,814 reviews

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.3
Good
2,814 reviews
Southwest
8.1
Very good
4,814 reviews

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,474 reviews
Southwest
8.1
Very good
4,814 reviews

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $112. Users have also found prices from $164 and $200 on Delta 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 $671. On average you can expect to pay $742. The most popular route, (Chicago Midway - Punta Cana), can usually be booked for $311.

  • 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 $640). 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.

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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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Simpson Bay flights
Midway to Montego Bay flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
Midway to Saint Thomas Island flights
Midway to Oranjestad flights
Midway to Nassau flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
Midway to Simpson Bay flights
Midway to Santo Domingo flights
Midway to George Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Kingston flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Road Town flights
O'Hare Intl to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Freeport flights
Midway to Kingston flights
Midway to Castries flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Havana flights
O'Hare Intl to The Valley flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Kingstown flights
Midway to Gregory Town flights
Midway to Georgetown flights
O'Hare Intl to Pointe-à-Pitre flights
Midway to Santiago de los Caballeros 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 December 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$519FlexibilityNo cancel feeOn-time62%
DeltaCheapest$375Average$755FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$671Average$879FlexibilityNo cancel feeOn-time63%
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