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Santiago de los Caballeros

$175+ Cheap flights from Midway (MDW) to Santiago de los Caballeros (STI)

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — STI
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1110:49 amMDW - STI
2 stops12h 19mDelta
Thu 12/186:35 amSTI - MDW
2 stops13h 25mDelta
Deal found 10/26$2,922

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$605
(Delta)

One-way from

$175
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$491
Provider with most accurate pricing for Chicago Midway-Santiago de los Caballeros flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Santiago de los Caballeros flights.
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From Chicago Midway to Santiago de los Caballeros
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One-way flight from Chicago Midway to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 28, 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

Sun 3/1

9:30 am-12:53 am

2 stops13h 23m

Santiago de los Caballeros

Thu 3/5

6:35 am-9:56 am

2 stops29h 21m

$605

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 2/16

1:00 pm-12:53 am

2 stops9h 53m

Santiago de los Caballeros

Mon 3/2

10:05 pm-12:35 pm

2 stops16h 30m

$955

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 12/11

10:49 am-1:08 am

2 stops12h 19m

Santiago de los Caballeros

Thu 12/18

6:35 am-6:00 pm

2 stops13h 25m

$2,922

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 1/1

6:12 am-2:42 am

2 stops18h 30m

$175

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Wed 12/17

2:49 pm-2:42 am

2 stops33h 53m

$466

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 12/18

6:12 am-2:42 am

2 stops18h 30m

$466

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 12/19

6:12 am-2:42 am

2 stops18h 30m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Midway to Santiago de los Caballeros

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 Midway to Santiago de los Caballeros in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 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 Chicago Midway Airport-Santiago de los Caballeros flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Santiago de los Caballeros flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Santiago de los Caballeros flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Santiago de los Caballeros 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 Chicago Midway Airport-Santiago de los Caballeros 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 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 $605, Delta can have you in Santiago de los Caballeros from Chicago Midway Airport in 13h 23m. 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.

See more FAQs

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