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$161+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$398
(eDestinos)

One-way from

$161
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$579
Provider with most accurate pricing for Santo Domingo Las Americas-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Santo Domingo Las Americas-Chicago Midway flights.
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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. 4% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This eDestinos deal was found by Cheapflights users on 1/15. 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.
Tue 2/101:41 pm
SDQ
-
MDW
2 stops47h 46m
Frontier
Tue 2/176:00 am
MDW
-
SDQ
2 stops51h 26m
Frontier
Deal found 1/15$398
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 3/1310:19 am
SDQ
-
MDW
1 stop28h 22m
Multiple Airlines
Mon 3/166:00 am
MDW
-
SDQ
1 stop9h 29m
Multiple Airlines
Deal found 1/15$409
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 4/43:35 pm
SDQ
-
MDW
2 stops53h 32m
Multiple Airlines
Mon 4/136:30 am
MDW
-
SDQ
1 stop8h 59m
Multiple Airlines
Deal found 1/13$425
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 3/13:32 pm
SDQ
-
MDW
2 stops30h 15m
Multiple Airlines
Sun 3/87:30 am
MDW
-
SDQ
1 stop20h 55m
Multiple Airlines
Deal found 1/15$426
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 4/22:30 pm
SDQ
-
MDW
2 stops30h 37m
Multiple Airlines
Mon 4/136:30 am
MDW
-
SDQ
1 stop8h 59m
Multiple Airlines
Deal found 1/14$429
This eDestinos deal was found by Cheapflights users on 1/14. 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.
Thu 2/2612:31 pm
SDQ
-
MDW
2 stops32h 07m
Frontier
Mon 3/26:00 am
MDW
-
SDQ
2 stops27h 56m
Frontier
Deal found 1/14$433
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 4/36:30 am
SDQ
-
MDW
2 stops14h 37m
Multiple Airlines
Mon 4/136:30 am
MDW
-
SDQ
1 stop8h 59m
Multiple Airlines
Deal found 1/14$442
This Kiwi.com deal was found by Cheapflights users on 1/14. 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
Sun 3/156:00 am
MDW
-
SDQ
2 stops18h 38m
Multiple Airlines
Deal found 1/14$446
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 2/277:10 pm
SDQ
-
MDW
2 stops28h 29m
Multiple Airlines
Sun 3/87:30 am
MDW
-
SDQ
1 stop20h 55m
Multiple Airlines
Deal found 1/15$472
This Delta deal was found by Cheapflights users on 1/15. 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 2/257:30 am
SDQ
-
MDW
2 stops12h 07m
Delta
Wed 3/410:49 am
MDW
-
SDQ
2 stops11h 43m
Delta
Deal found 1/15$477

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 15, 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 3/1

3:32 pm-7:47 pm

2 stops30h 15m

Chicago Midway

Sun 3/8

7:30 am-5:25 am

1 stop20h 55m

$426

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/1

2:59 am-8:07 pm

2 stops42h 08m

Chicago Midway

Mon 4/13

6:30 am-4:29 pm

1 stop8h 59m

$432

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 2/12

3:42 pm-10:31 pm

1 stop8h 49m

Chicago Midway

Tue 2/17

9:34 am-12:32 am

2 stops12h 58m

$477

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 4/4

3:35 pm-11:13 pm

2 stops32h 38m

Chicago Midway

Mon 4/13

6:30 am-4:29 pm

1 stop8h 59m

$478

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/1

7:10 pm-11:33 am

2 stops17h 23m

Chicago Midway

Mon 4/13

6:30 am-4:29 pm

1 stop8h 59m

$518

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 4/14

2:45 pm-10:29 pm

1 stop8h 44m

Chicago Midway

Mon 4/20

10:49 am-12:52 am

2 stops13h 03m

$581

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 2/10

7:30 am-10:22 pm

2 stops16h 52m

Chicago Midway

Tue 2/17

6:00 am-2:17 pm

1 stop6h 17m

$582

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

7:30 am-5:37 pm

2 stops12h 07m

Chicago Midway

Mon 3/2

6:00 am-2:17 pm

1 stop6h 17m

$582

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 2/26

12:31 pm-2:26 pm

1 stop27h 55m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 16 results
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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 January.
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 $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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