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$178+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$386
(Kiwi.com)

One-way from

$178
(Kiwi.com)

Popular in

August

Cheapest in

November

Average price

$454
From Santo Domingo Las Americas to Chicago Midway
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One-way flight from Santo Domingo Las Americas to Chicago Midway
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Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2912:56 pmSDQ - MDW
2 stops26h 37mMultiple Airlines
Tue 11/46:26 pmMDW - SDQ
1 stop20h 00mMultiple Airlines
Deal found 9/10$386
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/116:05 amSDQ - MDW
2 stops13h 20mDelta
Sat 10/2511:10 amMDW - SDQ
2 stops12h 17mDelta
Deal found 9/11$388
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 11/73:56 pmSDQ - MDW
1 stop8h 18mDelta
Mon 11/109:32 amMDW - SDQ
2 stops14h 04mDelta
Deal found 9/11$398
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/310:19 amSDQ - MDW
2 stops14h 22mMultiple Airlines
Tue 10/75:56 pmMDW - SDQ
1 stop21h 34mMultiple Airlines
Deal found 9/10$402
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/183:35 pmSDQ - MDW
2 stops16h 50mMultiple Airlines
Thu 10/236:20 amMDW - SDQ
1 stop6h 39mMultiple Airlines
Deal found 9/10$413
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/256:05 amSDQ - MDW
2 stops13h 20mDelta
Fri 10/319:35 amMDW - SDQ
2 stops13h 52mDelta
Deal found 9/11$420
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/93:14 pmSDQ - MDW
1 stop9h 32mFrontier
Thu 10/166:20 amMDW - SDQ
1 stop6h 39mFrontier
Deal found 9/9$445
This Frontier deal was found by Cheapflights users on 9/10. 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 10/303:19 pmSDQ - MDW
1 stop7h 44mFrontier
Mon 11/36:20 amMDW - SDQ
2 stops9h 01mFrontier
Deal found 9/10$476
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 10/32:50 pmSDQ - MDW
1 stop7h 46mDelta
Mon 10/69:35 amMDW - SDQ
2 stops13h 52mDelta
Deal found 9/11$478
This Delta deal was found by Cheapflights users on 9/10. 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 10/32:50 pmSDQ - MDW
1 stop7h 46mDelta
Tue 10/76:00 amMDW - SDQ
1 stop6h 41mDelta
Deal found 9/10$524

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 September 11, 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

Wed 10/29

12:56 pm-2:33 pm

2 stops26h 37m

Chicago Midway

Tue 11/4

6:26 pm-4:26 pm

1 stop20h 00m

$386

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 10/11

6:05 am-6:25 pm

2 stops13h 20m

Chicago Midway

Sat 10/25

11:10 am-12:27 am

2 stops12h 17m

$388

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 11/7

3:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Mon 11/10

9:32 am-1:36 am

2 stops14h 04m

$398

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 10/18

3:35 pm-7:25 am

2 stops16h 50m

Chicago Midway

Thu 10/23

6:20 am-1:59 pm

1 stop6h 39m

$413

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 10/25

6:05 am-6:25 pm

2 stops13h 20m

Chicago Midway

Fri 10/31

9:35 am-12:27 am

2 stops13h 52m

$420

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 10/25

6:05 am-6:25 pm

2 stops13h 20m

Chicago Midway

Sat 11/1

1:11 pm-12:27 am

2 stops10h 16m

$420

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 10/29

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Tue 11/4

6:00 am-2:41 pm

1 stop6h 41m

$420

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:14 pm-11:46 pm

1 stop9h 32m

Chicago Midway

Thu 10/16

6:20 am-1:59 pm

1 stop6h 39m

$445

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Mon 11/3

6:20 am-5:21 pm

2 stops9h 01m

$476

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:35 pm-11:27 am

1 stop20h 52m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 17 results
1
2

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 $388, Delta can have you in Chicago Midway Airport from Santo Domingo in 13h 20m. 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.

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

    Currently, April is the cheapest month in which you can book a flight from Santo Domingo to Chicago Midway Airport (average of $160). Flying from Santo Domingo to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

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

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