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$176+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 5/106:10 am
SDQ
-
MDW
1 stop31h 50m
Multiple Airlines
Sat 5/167:30 am
MDW
-
SDQ
1 stop20h 59m
Multiple Airlines
Deal found 1/27$379
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/73:35 pm
SDQ
-
MDW
2 stops22h 10m
Multiple Airlines
Mon 2/97:00 pm
MDW
-
SDQ
1 stop15h 26m
Multiple Airlines
Deal found 1/25$388
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/2510:19 am
SDQ
-
MDW
1 stop8h 29m
Multiple Airlines
Wed 4/16:00 am
MDW
-
SDQ
1 stop7h 53m
Multiple Airlines
Deal found 1/27$409
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/126:10 am
SDQ
-
MDW
1 stop7h 52m
Multiple Airlines
Thu 3/192:41 pm
MDW
-
SDQ
2 stops9h 57m
Multiple Airlines
Deal found 1/26$457
This Delta deal was found by Cheapflights users on 1/27. 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 2/253:42 pm
SDQ
-
MDW
1 stop8h 49m
Delta
Wed 3/410:49 am
MDW
-
SDQ
2 stops11h 43m
Delta
Deal found 1/27$477
This Delta deal was found by Cheapflights users on 1/25. 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 2/53:46 pm
SDQ
-
MDW
1 stop8h 36m
Delta
Sun 2/86:00 am
MDW
-
SDQ
1 stop6h 21m
Delta
Deal found 1/25$489
This Delta deal was found by Cheapflights users on 1/25. 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 2/23:46 pm
SDQ
-
MDW
1 stop8h 36m
Delta
Tue 2/106:35 pm
MDW
-
SDQ
2 stops17h 46m
Delta
Deal found 1/25$541
This Delta deal was found by Cheapflights users on 1/27. 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 3/166:35 am
SDQ
-
MDW
2 stops12h 19m
Delta
Tue 3/241:10 pm
MDW
-
SDQ
2 stops9h 43m
Delta
Deal found 1/27$582

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(Kiwi.com)

One-way from

$176
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$573
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. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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

Sun 5/10

6:10 am-1:00 pm

1 stop31h 50m

Chicago Midway

Sat 5/16

7:30 am-5:29 am

1 stop20h 59m

$379

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 3/25

10:19 am-5:48 pm

1 stop8h 29m

Chicago Midway

Wed 4/1

6:00 am-2:53 pm

1 stop7h 53m

$409

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 3/12

6:10 am-1:02 pm

1 stop7h 52m

Chicago Midway

Thu 3/19

2:41 pm-1:38 am

2 stops9h 57m

$457

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/25

3:42 pm-10:31 pm

1 stop8h 49m

Chicago Midway

Wed 3/4

10:49 am-12:32 am

2 stops11h 43m

$477

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

3:42 pm-10:31 pm

1 stop8h 49m

Chicago Midway

Mon 3/2

10:49 am-12:32 am

2 stops11h 43m

$477

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/19

12:31 pm-2:26 pm

1 stop27h 55m

$181

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 2/8

3:32 pm-11:45 am

2 stops22h 13m

$192

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/12

12:31 pm-2:26 pm

1 stop27h 55m

$197

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/12

3:32 pm-5:53 pm

2 stops28h 21m

$204

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 2/7

3:30 pm-11:45 am

2 stops22h 15m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 17 results
1
2
  • Most accurate provider: When it comes to deals on Santo Domingo-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santo Domingo-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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 $477, Delta can have you in Chicago Midway Airport from Santo Domingo in 8h 49m. 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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