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$213+ Cheap flights from Santo Domingo (SDQ) to Midway (MDW)

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Santo Domingo to Midway

Cheapest flights from Santo Domingo to Midway
Explore the most affordable flight options available from Santo Domingo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Frontier deal was found by Cheapflights users on 12/11. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Wed 1/75:10 pmMDW - SDQ
2 stops14h 31mFrontier
Deal found 12/11$339
This Frontier deal was found by Cheapflights users on 12/11. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Thu 1/812:41 pmMDW - SDQ
2 stops21h 14mFrontier
Deal found 12/11$344
This Frontier deal was found by Cheapflights users on 12/11. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Sat 1/106:10 amMDW - SDQ
1 stop7h 18mFrontier
Deal found 12/11$353
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/233:35 pmSDQ - MDW
1 stop25h 02mMultiple Airlines
Wed 1/75:10 pmMDW - SDQ
1 stop20h 08mMultiple Airlines
Deal found 12/11$356
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/222:53 pmSDQ - MDW
1 stop9h 05mFrontier
Wed 1/75:10 pmMDW - SDQ
2 stops14h 31mFrontier
Deal found 12/11$361
This Frontier deal was found by Cheapflights users on 12/11. 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 12/222:53 pmSDQ - MDW
1 stop9h 05mFrontier
Thu 1/812:41 pmMDW - SDQ
2 stops21h 14mFrontier
Deal found 12/11$369
This Frontier deal was found by Cheapflights users on 12/11. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Sun 1/116:10 amMDW - SDQ
1 stop7h 04mFrontier
Deal found 12/11$394
This Frontier deal was found by Cheapflights users on 12/11. 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 12/2410:41 amSDQ - MDW
2 stops13h 31mFrontier
Thu 1/86:10 amMDW - SDQ
1 stop7h 08mFrontier
Deal found 12/11$400
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/222:53 pmSDQ - MDW
1 stop9h 05mMultiple Airlines
Tue 1/136:30 pmMDW - SDQ
1 stop8h 55mMultiple Airlines
Deal found 12/11$405
This Frontier deal was found by Cheapflights users on 12/11. 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 12/222:53 pmSDQ - MDW
1 stop9h 05mFrontier
Sun 1/116:10 amMDW - SDQ
1 stop7h 04mFrontier
Deal found 12/11$419
This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/243:57 pmSDQ - MDW
1 stop8h 25mDelta
Fri 1/95:31 pmMDW - SDQ
2 stops17h 51mDelta
Deal found 12/11$423

Find flight deals from Santo Domingo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Santo Domingo (SDQ) to Midway (MDW). 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 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$339
(Frontier)

One-way from

$213
(Frontier)

Popular in

May

Cheapest in

December

Average price

$412
Provider with most accurate pricing for Santo Domingo Las Americas-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Santo Domingo Las Americas-Chicago Midway flights.
Search Deals
From Santo Domingo Las Americas to Chicago Midway
Search Deals
One-way flight from Santo Domingo Las Americas to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Santo Domingo to Midway 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 12, 2025.
Use the filters below to find and compare flights from Santo Domingo to Chicago Midway Airport that are best for you.

Fly from

Santo Domingo

Fly to

Midway

Route

Depart

Return

Price

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 12/23

12:35 pm-9:58 pm

1 stop11h 23m

Chicago Midway

Wed 1/7

5:10 pm-9:41 am

2 stops14h 31m

$339

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 12/23

12:35 pm-9:58 pm

1 stop11h 23m

Chicago Midway

Thu 1/8

12:41 pm-11:55 am

2 stops21h 14m

$344

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 12/22

2:53 pm-9:58 pm

1 stop9h 05m

Chicago Midway

Sat 1/10

6:10 am-3:28 pm

1 stop7h 18m

$378

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 12/22

12:35 pm-9:58 pm

1 stop11h 23m

Chicago Midway

Thu 1/8

6:10 am-3:18 pm

1 stop7h 08m

$378

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 12/24

10:41 am-10:12 pm

2 stops13h 31m

Chicago Midway

Thu 1/8

6:10 am-3:18 pm

1 stop7h 08m

$400

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 12/24

10:41 am-10:12 pm

2 stops13h 31m

Chicago Midway

Sat 1/10

6:10 am-3:28 pm

1 stop7h 18m

$400

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 12/22

2:53 pm-9:58 pm

1 stop9h 05m

Chicago Midway

Sun 1/11

6:10 am-3:14 pm

1 stop7h 04m

$419

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 12/25

3:57 pm-10:22 pm

1 stop8h 25m

Chicago Midway

Thu 1/8

11:21 am-1:10 pm

2 stops23h 49m

$423

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 12/24

3:57 pm-10:22 pm

1 stop8h 25m

Chicago Midway

Mon 1/12

6:45 am-12:30 am

2 stops15h 45m

$423

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 12/24

3:57 pm-10:22 pm

1 stop8h 25m

Chicago Midway

Tue 1/13

6:45 am-12:30 am

2 stops15h 45m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 17 results
1
2

Compare providers for flights from Santo Domingo to Midway

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 Santo Domingo to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Santo Domingo-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Santo Domingo-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Santo Domingo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Santo Domingo-Chicago Midway Airport 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 Santo Domingo-Chicago Midway Airport 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 Santo Domingo to Midway

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

Related info for your journey

Find useful and relevant information for your journey from Santo Domingo to Midway. 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 from for flights from Santo Domingo to Chicago Midway?

    For a flight from Santo Domingo to Chicago Midway, you will be flying from Las Americas. Santo Domingo Las Americas (SDQ) is just 17.5 mi from the center of the city. Las Americas is the only Santo Domingo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Santo Domingo Las Americas on a regular basis.

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

    For as low as $339, Frontier can have you in Chicago Midway Airport from Santo Domingo in 11h 23m. Santo Domingo and Chicago Midway Airport are separated by a distance of 1932 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Santo Domingo to Midway 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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