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Santo Domingo

$180+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDQ
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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Cheap 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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$330
(Kiwi.com)

One-way from

$180
(Delta)

Popular in

April

Cheapest in

March

Average price

$426
Provider with most accurate pricing for Chicago Midway-Santo Domingo Las Americas flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Santo Domingo Las Americas flights.
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From Chicago Midway to Santo Domingo Las Americas
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One-way flight from Chicago Midway to Santo Domingo Las Americas
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 8% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:06 pmMDW - SDQ
1 stop22h 50mFrontier
Sun 11/24:19 pmSDQ - MDW
1 stop28h 20mFrontier
Deal found 9/24$330
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:06 pmMDW - SDQ
1 stop22h 50mMultiple Airlines
Sun 11/24:54 pmSDQ - MDW
2 stops27h 45mMultiple Airlines
Deal found 9/24$353
This Mytrip deal was found by Cheapflights users on 9/23. 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.
Thu 10/96:20 amMDW - SDQ
1 stop6h 39mFrontier
Sun 10/123:14 pmSDQ - MDW
1 stop18h 17mFrontier
Deal found 9/23$379
This Frontier deal was found by Cheapflights users on 9/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:15 amMDW - SDQ
1 stop6h 41mFrontier
Sun 11/164:19 pmSDQ - MDW
1 stop7h 44mFrontier
Deal found 9/24$380
This Delta deal was found by Cheapflights users on 9/24. 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.
Sat 10/181:11 pmMDW - SDQ
2 stops10h 16mDelta
Sat 10/256:05 amSDQ - MDW
2 stops13h 20mDelta
Deal found 9/24$385
This Delta deal was found by Cheapflights users on 9/24. 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 11/111:15 pmMDW - SDQ
2 stops10h 21mDelta
Sat 11/157:01 amSDQ - MDW
2 stops13h 07mDelta
Deal found 9/24$388
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:26 pmMDW - SDQ
1 stop20h 00mMultiple Airlines
Tue 11/186:10 amSDQ - MDW
1 stop19h 45mMultiple Airlines
Deal found 9/24$404
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:30 amMDW - SDQ
2 stops13h 15mMultiple Airlines
Sun 11/164:19 pmSDQ - MDW
1 stop7h 44mMultiple Airlines
Deal found 9/24$406
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:30 amMDW - SDQ
2 stops9h 20mMultiple Airlines
Sun 11/164:19 pmSDQ - MDW
1 stop7h 44mMultiple Airlines
Deal found 9/24$409
This Delta deal was found by Cheapflights users on 9/23. 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 10/41:08 pmMDW - SDQ
2 stops10h 28mDelta
Tue 10/76:05 amSDQ - MDW
2 stops13h 20mDelta
Deal found 9/23$413
This Frontier deal was found by Cheapflights users on 9/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:15 amMDW - SDQ
2 stops9h 06mFrontier
Sun 11/164:19 pmSDQ - MDW
1 stop7h 44mFrontier
Deal found 9/24$420

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 September 25, 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

Sat 10/18

11:10 am-12:27 am

2 stops12h 17m

Santo Domingo Las Americas

Tue 10/21

6:05 am-6:25 pm

2 stops13h 20m

$385

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 11/10

1:15 pm-1:36 am

2 stops10h 21m

Santo Domingo Las Americas

Sat 11/15

7:01 am-6:18 pm

2 stops13h 17m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 11/12

1:15 pm-1:36 am

2 stops10h 21m

Santo Domingo Las Americas

Sat 11/15

7:01 am-6:08 pm

2 stops13h 07m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 11/11

1:15 pm-1:36 am

2 stops10h 21m

Santo Domingo Las Americas

Sat 11/15

7:01 am-6:08 pm

2 stops13h 07m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 11/8

11:10 am-1:27 am

2 stops12h 17m

Santo Domingo Las Americas

Sat 11/15

7:01 am-6:08 pm

2 stops13h 07m

$388

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 11/11

6:00 am-2:42 pm

1 stop6h 42m

Santo Domingo Las Americas

Tue 11/18

3:57 pm-11:40 pm

1 stop9h 43m

$406

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 11/12

9:34 am-1:36 am

2 stops14h 02m

Santo Domingo Las Americas

Wed 11/19

6:45 am-6:08 pm

2 stops13h 23m

$411

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 11/8

6:30 am-9:45 pm

2 stops13h 15m

Santo Domingo Las Americas

Sat 11/15

3:35 pm-9:22 pm

1 stop7h 47m

$424

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 10/30

9:35 am-12:27 am

2 stops13h 52m

Santo Domingo Las Americas

Fri 11/7

3:56 pm-10:14 pm

1 stop8h 18m

$454

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 11/8

1:06 pm-1:27 am

2 stops10h 21m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 20 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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Santo Domingo flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 September 25, 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
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 12h 17m. 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 29% 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Santo Domingo?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Santo Domingo (average of $362). Flying from Chicago Midway Airport to Santo Domingo in December is currently the most expensive (average of $583). 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

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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$406Average$604FlexibilityNo cancel feeOn-timeN/A

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