The cheapest times to fly from MDW to STI are

  • January 1st to March 11th
  • August 27th to December 9th

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from MDW to STI is late January and early February. Prices can be as high as $2304 for Sunday flights during early to mid July, or as low as $429 for Tuesday flights around late January and early February.


When to Fly to Santiago De Los Caballeros

Flying from Chicago, IL (MDW) to Santiago (STI) will usually cost between $429 to $1432 per person if booking more than four weeks in advance. On average the very cheapest time to fly is late January and early February with an average ticket price of $429. Due to high demand the most expensive time to fly is early to mid July, with an average price of $1541. Planning your trip to low-cost times can easily save you $1112 on economy flights and even more on first-class flights. Generally, any price below $644 can be considered a good price for a round-trip MDW to STI flight.

See below for a graph of average weekly prices for the MDW to STI route. All prices are for round-trip tickets in USD.

MDW to STI Flight Prices

Compared to other flights, the MDW to STI flight is cheaper than the average and costs less than the average flight leaving from Chicago. The average price per mile (for a direct flight) is $0.22, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $452 (35%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $597. Return trip prices are from the STI to MDW flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from MDW to STI can generally find a 2-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 4 hour 18 minutes may not be realistic.


Alternative Nearby Airports

Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is not usually a nonstop flight from MDW to STI while comparing.

Destination alternative #1: De Las Americas International Airport (SDQ) in Santo Domingo

  • 91 miles (146 km) away from STI
  • Usually 23.68% less expensive than STI
  • 1-layover flights available

See MDW to SDQ flights

Destination alternative #2: Port Au Prince International Airport (PAP) in Port-au-Prince

  • 124 miles (200 km) away from STI
  • Usually 18.17% less expensive than STI
  • 1-layover flights available

See MDW to PAP flights


Flight Hacking MDW to STI

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from MDW to STI — but Champion Traveler does!

Hack #1: Fort Lauderdale, FL (MDW > FLL > STI)

  • Price for both tickets: $615
  • Average savings: $30 (4.58%)

See MDW to FLL flights


Flight Questions Answered

Still have questions about flying from MDW to STI? We’ve got answers.

Which airlines fly this route?

You can find 2 major airlines flying this route most often: Delta, Seaborne Airlines, and potentially more during busy seasons.

How far away is it from Cibao International Airport to Chicago Midway International Airport?

The distance between the two airports is roughly 1844 miles or 2968 kilometers.

How long does it take to fly from MDW to STI?

The real-world flight time for a nonstop MDW to STI flight is about 4 hour 18 minutes.

How many flights go between Chicago, IL and Santiago?

It depends on the day of the week and the date, but a typical day might have around 53 available flights from MDW to STI.


Airport Location Info


Departing Airport

Origination code MDW
Origination airport name Chicago Midway International Airport
City Chicago, IL
Country the United States
Latitude 41.8
Longitude -87.8

Return Airport

Destination code STI
Destination airport name Cibao International Airport
City Santiago
Country Dominican Republic
Latitude 19.4
Longitude -70.6


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.