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Santo Domingo

$152+ Cheap flights from Midway (MDW) to Santo Domingo (SDQ)

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDQ
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Midway to Santo Domingo

Cheapest flights from Midway to Santo Domingo
Explore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/88:42 pmMDW - SDQ
2 stops41h 47mMultiple Airlines
Mon 12/222:53 pmSDQ - MDW
1 stop9h 05mMultiple Airlines
Deal found 12/2$357
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/72:59 pmMDW - SDQ
1 stop23h 30mMultiple Airlines
Sun 12/218:20 amSDQ - MDW
1 stop14h 44mMultiple Airlines
Deal found 12/2$418
This Delta deal was found by Cheapflights users on 12/3. 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 12/66:00 amMDW - SDQ
1 stop6h 42mDelta
Wed 12/103:57 pmSDQ - MDW
1 stop9h 50mDelta
Deal found 12/3$440
This eDestinos deal was found by Cheapflights users on 12/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - SDQ
2 stops23h 27mFrontier
Wed 12/316:04 pmSDQ - MDW
2 stops30h 08mFrontier
Deal found 12/2$445
This Priceline deal was found by Cheapflights users on 12/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - SDQ
1 stop7h 12mFrontier
Sun 12/2112:35 pmSDQ - MDW
1 stop10h 29mFrontier
Deal found 12/2$459
This Frontier deal was found by Cheapflights users on 12/3. 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.
Wed 12/172:49 pmMDW - SDQ
2 stops16h 53mFrontier
Sat 12/2711:16 amSDQ - MDW
1 stop11h 48mFrontier
Deal found 12/3$491
This Delta deal was found by Cheapflights users on 12/1. 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 12/56:00 amMDW - SDQ
1 stop6h 42mDelta
Sat 12/133:57 pmSDQ - MDW
1 stop9h 50mDelta
Deal found 12/1$494
This Frontier deal was found by Cheapflights users on 12/2. 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.
Thu 12/186:33 pmMDW - SDQ
2 stops14h 47mFrontier
Mon 12/222:53 pmSDQ - MDW
1 stop9h 05mFrontier
Deal found 12/2$508

Find flight deals from Midway to Santo Domingo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Santo Domingo (SDQ). 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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$305
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

August

Cheapest in

March

Average price

$656
Provider with most accurate pricing for Chicago Midway-Santo Domingo Las Americas flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Santo Domingo Las Americas flights.
Search Deals
From Chicago Midway to Santo Domingo Las Americas
Search Deals
One-way flight from Chicago Midway to Santo Domingo Las Americas
Search Deals
High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Santo Domingo 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 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Santo Domingo that are best for you.

Fly from

Midway

Fly to

Santo Domingo

Route

Depart

Return

Price

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/18

8:19 pm-4:29 pm

1 stop18h 10m

Santo Domingo Las Americas

Sun 1/25

11:04 am-10:19 pm

2 stops13h 15m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 2/18

3:42 pm-10:42 pm

1 stop9h 00m

$390

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 2/18

6:00 am-2:17 pm

1 stop6h 17m

Santo Domingo Las Americas

Wed 2/25

7:30 am-11:59 am

2 stops30h 29m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 2/16

6:17 pm-12:32 am

2 stops28h 15m

Santo Domingo Las Americas

Wed 2/25

7:30 am-10:42 pm

2 stops17h 12m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 2/21

6:00 am-3:30 pm

1 stop7h 30m

Santo Domingo Las Americas

Wed 2/25

7:30 am-10:42 pm

2 stops17h 12m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 2/22

9:34 am-2:17 pm

2 stops26h 43m

Santo Domingo Las Americas

Wed 2/25

2:31 pm-9:56 am

2 stops21h 25m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 2/20

6:40 pm-7:14 pm

2 stops22h 34m

Santo Domingo Las Americas

Wed 2/25

7:30 am-10:42 pm

2 stops17h 12m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 1/26

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Tue 2/3

7:30 am-10:22 pm

2 stops16h 52m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/25

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Tue 2/3

7:30 am-10:22 pm

2 stops16h 52m

$394

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 1/22

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 1/28

7:30 am-5:29 pm

2 stops11h 59m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Santo Domingo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Santo Domingo in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Santo Domingo flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Santo Domingo flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Santo Domingo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Santo Domingo flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Santo Domingo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Santo Domingo

Have a flexible travel schedule? Discover the best time to fly to Santo Domingo 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.

Reviews of airlines servicing Santo Domingo

Get insights into the airlines that provide service to Santo Domingo. 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 Santo Domingo. Reviews last updated December 4, 2025.
Read reviews from past customers who have flown Delta from Chicago Midway Airport to Santo Domingo. 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.
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Midway to Santo Domingo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Santo Domingo from Chicago Midway?

    Located just 17.5 mi from the city center, Santo Domingo Las Americas is the airport most travelers will use when flying to Santo Domingo from Chicago Midway. Booking flights from Chicago Midway to Las Americas (SDQ) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • How long is the flight from Chicago Midway Airport to Santo Domingo?

    Delta can get you from Chicago Midway Airport to Santo Domingo in just under 6h 21m. Your travel time can differ by up to . Airlines will cover a distance of 1932 mi.

  • What is the cheapest airline to fly from Chicago Midway Airport to Santo Domingo round-trip?

    Flying on Delta is currently your cheapest option to Santo Domingo, with prices starting at $406. Delta is 32% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Midway to Santo Domingo that include hotel bookings?

    Yes. In addition to deals on Midway to Santo Domingo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Santo Domingo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Santo Domingo.

  • Can I find deals for business class flights from Midway to Santo Domingo?

    Yes. Cheapflights offers flight deals from Midway to Santo Domingo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Santo Domingo?

Book flights to Santo Domingo if you plan to visit one of these locations
Juan Dolio

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Top airline flying from Midway to Santo Domingo

Discover the top airline that operate flights from Midway to Santo Domingo. 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$406Average$654FlexibilityNo cancel feeOn-timeN/A

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