HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$191+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Santo Domingo to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/43:35 pmSDQ - MDW
1 stop8h 18mMultiple Airlines
Thu 12/112:16 pmMDW - SDQ
2 stops33h 34mMultiple Airlines
Deal found 10/28$326
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 12/2312:35 pmSDQ - MDW
1 stop11h 23mFrontier
Thu 1/13:10 pmMDW - SDQ
1 stop18h 10mFrontier
Deal found 10/27$338
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/2011:16 amSDQ - MDW
1 stop11h 48mFrontier
Sat 1/32:16 pmMDW - SDQ
1 stop19h 14mFrontier
Deal found 10/29$362
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/43:35 pmSDQ - MDW
1 stop8h 18mMultiple Airlines
Wed 12/102:49 pmMDW - SDQ
2 stops12h 36mMultiple Airlines
Deal found 10/28$374
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2610:19 amSDQ - MDW
1 stop8h 38mMultiple Airlines
Sun 12/76:37 pmMDW - SDQ
2 stops18h 46mMultiple Airlines
Deal found 10/28$388
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 12/2212:35 pmSDQ - MDW
1 stop11h 23mFrontier
Mon 12/293:10 pmMDW - SDQ
1 stop18h 10mFrontier
Deal found 10/27$394
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/276:00 amSDQ - MDW
2 stops18h 43mMultiple Airlines
Thu 12/42:16 pmMDW - SDQ
1 stop24h 13mMultiple Airlines
Deal found 10/27$396
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/203:23 pmSDQ - MDW
1 stop7h 41mMultiple Airlines
Sat 1/32:16 pmMDW - SDQ
2 stops10h 38mMultiple Airlines
Deal found 10/29$411
This Delta deal was found by Cheapflights users on 10/27. 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 11/173:57 pmSDQ - MDW
1 stop9h 43mDelta
Wed 12/310:49 amMDW - SDQ
2 stops12h 59mDelta
Deal found 10/27$424
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/2610:19 amSDQ - MDW
1 stop8h 38mMultiple Airlines
Sat 12/66:00 amMDW - SDQ
2 stops18h 26mMultiple Airlines
Deal found 10/27$428

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$326
(Kiwi.com)

One-way from

$191
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$480
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. 1% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 29, 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

Thu 1/1

3:10 pm-11:20 am

1 stop18h 10m

$338

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 11/26

10:19 am-4:57 pm

1 stop8h 38m

Chicago Midway

Sun 12/7

6:37 pm-3:23 pm

2 stops18h 46m

$388

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 12/20

3:23 pm-9:04 pm

1 stop7h 41m

Chicago Midway

Sat 1/3

2:16 pm-2:54 am

2 stops10h 38m

$411

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 11/26

10:19 am-4:57 pm

1 stop8h 38m

Chicago Midway

Sat 12/6

6:00 am-2:26 am

2 stops18h 26m

$428

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 11/13

4:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Sun 11/16

6:15 am-2:56 pm

1 stop6h 41m

$439

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 12/4

4:39 pm-7:42 pm

1 stop29h 03m

Chicago Midway

Wed 12/10

2:49 pm-3:19 pm

1 stop22h 30m

$445

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 11/20

3:57 pm-11:40 pm

1 stop9h 43m

Chicago Midway

Thu 11/27

9:34 am-1:36 am

2 stops14h 02m

$494

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 11/17

3:57 pm-11:40 pm

1 stop9h 43m

Chicago Midway

Wed 12/3

10:49 am-1:48 am

2 stops12h 59m

$494

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 2/13

3:40 pm-9:46 pm

1 stop8h 06m

Chicago Midway

Tue 2/17

5:25 pm-11:59 pm

2 stops28h 34m

$528

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 12/30

3:59 am-10:12 pm

2 stops20h 13m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 16 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 October.
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 $338, 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Santo Domingo to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Santo Domingo to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.