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 $612). 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.

In terms of precipitation, rainfall in Santiago de los Caballeros ranges from 3.0 - 11.6 inches per month. December is typically the wettest month, when rainfall can reach 11.6 in. July is typically the driest time to visit Santiago de los Caballeros when rainfall is around 3.0 in.

If weather is an important factor for your trip to Santiago de los Caballeros, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

What is the cheapest month to fly from Chicago Midway Airport to Santiago de los Caballeros?

Flights from Chicago Midway Airport to Santiago de los Caballeros lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to Santiago de los Caballeros in September, with the cheapest ticket starting at $229.

What is the cheapest time of day to fly from MDW to STI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Santiago de los Caballeros as you normally would.

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.

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.

$538+ Flights from Chicago Midway Airport to Santiago de los Caballeros

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Cheap flight deals from Midway to Santiago de los Caballeros

Round-trip from	$538 (Trip.com)
Popular in	December
Cheapest in	September
Average price	$675

From Chicago Midway to Santiago de los Caballeros

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Highest demand for flights based on searches. 9% potential increase in price ($60 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).

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Average for round-trip flights in July 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 July 29, 2025.

Fri 9/195:15 pmMDW - STI

2 stops16h 50mMultiple Airlines

Mon 9/2212:10 pmSTI - MDW

2 stops12h 10mMultiple Airlines

Deal found 7/28

$538

Thu 9/116:00 amMDW - STI

2 stops12h 11mDelta

Thu 9/182:45 pmSTI - MDW

2 stops19h 55mDelta

Deal found 7/28

$1,921

Best flights from Midway to Santiago de los Caballeros
Discover carefully curated flight deals from Midway to Santiago de los Caballeros that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2025.

Fri 9/195:15 pmMDW - STI

2 stops16h 50mMultiple Airlines

Mon 9/2212:10 pmSTI - MDW

2 stops12h 10mMultiple Airlines

Deal found 7/28

$538

Thu 9/116:00 amMDW - STI

2 stops12h 11mDelta

Thu 9/182:45 pmSTI - MDW

2 stops19h 55mDelta

Deal found 7/28

$1,921

Cheapflights Fare Finder

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

Fly to

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 9/19

5:15 pm-11:05 am

2 stops16h 50m

Santiago de los Caballeros

Mon 9/22

12:10 pm-11:20 pm

2 stops12h 10m

$538

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 9/11

6:00 am-7:11 pm

2 stops12h 11m

Santiago de los Caballeros

Thu 9/18

2:45 pm-9:40 am

2 stops19h 55m

$1,921

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.

Reviews of airlines servicing Santiago de los Caballeros

Peruse reviews from past customers who have flown with Delta from Chicago Midway Airport to Santiago de los Caballeros to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,977 reviews

Delta

8.0

Very good

7,977 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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.
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 $612). 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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$538+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Santiago de los Caballeros with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Santiago de los Caballeros

Round-trip from

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Find flight deals from Midway to Santiago de los Caballeros

Cheapest flights from Midway to Santiago de los CaballerosExplore 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 July 29, 2025.

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 July 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Santiago de los Caballeros that are best for you.

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.

Reviews of airlines servicing Santiago de los Caballeros

Peruse reviews from past customers who have flown with Delta from Chicago Midway Airport to Santiago de los Caballeros to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

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

How can I 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?

What is the cheapest month to book a flight from Chicago Midway Airport to Santiago de los Caballeros?

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 Midway to Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.

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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 July 29, 2025.