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Santiago de los Caballeros

$2,142+ Cheap flights from Midway (MDW) to Santiago de los Caballeros (STI)

This is the cheapest round-trip 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.
MDW — STI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Santiago de los Caballeros (STI). 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

$640
(Delta)

Popular in

December

Cheapest in

September

Average price

$361
From Chicago Midway to Santiago de los Caballeros
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Highest demand for flights based on searches. 11% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 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 Midway to Santiago de los Caballeros

Cheapest flights from Midway to Santiago de los Caballeros
Explore the most affordable flight options available from Midway to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/99:35 amMDW - STI
2 stops13h 49mDelta
Tue 10/216:00 amSTI - MDW
2 stops13h 25mDelta
Deal found 9/9$2,142
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1110:35 amMDW - STI
2 stops12h 59mDelta
Thu 9/182:45 pmSTI - MDW
2 stops19h 55mDelta
Deal found 9/9$2,223

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Santiago de los Caballeros 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 Chicago Midway Airport to Santiago de los Caballeros that are best for you.

Fly from

Midway

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 10/9

9:35 am-12:24 am

2 stops13h 49m

Santiago de los Caballeros

Tue 10/21

6:00 am-6:25 pm

2 stops13h 25m

$2,142

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Best time to book a flight from Midway to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from Midway 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 Midway to Santiago de los Caballeros. 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 into for flights to Santiago de los Caballeros from Chicago Midway?

    Santiago de los Caballeros (STI), located 6.8 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Santiago de los Caballeros. 0 airlines have flights to Santiago from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Santiago de los Caballeros should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Santiago de los Caballeros?

    For as low as $2,142, Delta can have you in Santiago de los Caballeros from Chicago Midway Airport in 13h 49m. There are 1843 mi between Chicago Midway Airport and Santiago de los Caballeros.

  • Can I find deals for flights from Midway to Santiago de los Caballeros that include hotel bookings?

    Yes. In addition to deals on Midway to Santiago de los Caballeros flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Santiago de los Caballeros?

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

  • Can I find deals for business class flights from Midway to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Midway to Santiago de los Caballeros 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 Chicago Midway Airport to Santiago de los Caballeros?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Santiago de los Caballeros (average of $347). Flying from Chicago Midway Airport to Santiago de los Caballeros in July is currently the most expensive (average of $600). 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.

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