To save on the cost of your flight from Chicago Midway Airport to Santiago de los Caballeros, book at least 25 days before your planned departure. Booking around this time can save you about 116% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $404 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $672.
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 April, with the cheapest ticket starting at $207.
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.
Fly from
Fly to
Budget
$509 - $2,656
Route
Depart
Return
Price
Chicago MidwaySantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Sat 10/19
2 stops12h 27m
Santiago de los Caballeros
Tue 10/29
2 stops19h 26m
Chicago MidwaySantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Sat 6/8
2 stops17h 48m
Santiago de los Caballeros
Sat 6/15
2 stops18h 41m
Chicago MidwaySantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Mon 7/29
2 stops17h 44m
Santiago de los Caballeros
Sat 8/3
2 stops11h 54m
Chicago MidwaySantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Mon 7/22
2 stops17h 44m
Santiago de los Caballeros
Thu 8/1
2 stops18h 32m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Crew
Entertainment
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Overall
Crew
Entertainment
Food
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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