
Flight Deals from Chicago to Santiago from $144
Top flight deals from leading airlines:







... and +100s more
Save up to 50% on select flights with Priceline
Save an average of $240 per person when bundling your flight and hotel together with Priceline
If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference
We’re always here for you - reach us 24 hours a day, 7 days a week
Price Drop Deals Near You
Stops
- Up to 1 stop$343
- Up to 2 stops$499
Airlines
- American Airlines$495
- JetBlue$520
- Spirit Airlines$343
- United Airlines$522
Cabin Class
- Economy$343
Departure Airports
- Chicago O Hare Airport$343
Arrival Airports
- Cibao International Airport$343
Layover Airports
- Charlotte Douglas International Airport$499
- Fort Lauderdale Hollywood International Airport$343
- General Edward Lawrence Logan International Airport$520
- Miami International Airport$495
- New York John F Kennedy Airport$520
- Newark Liberty Airport$522
- Reagan Washington National Airport$499
Best Price. GUARANTEED.
Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/19/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/12/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25

09/12/25
09/13/25

09/19/25
09/20/25
Top Deals on flights from Chicago to Santiago
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 9
as low as
$144
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 8
as low as
$199
Chicago, US (CHI) - Santiago, DO (STI)

Sep 12
Sep 12
as low as
$199
Chicago, US (CHI) - Santiago, DO (STI)

Aug 26
Aug 27
as low as
$238
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 9
as low as
$242
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 9
as low as
$248
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 9
as low as
$259
Chicago, US (CHI) - Santiago, DO (STI)

Aug 29
Aug 30
as low as
$278
Chicago, US (CHI) - Santiago, DO (STI)

Sep 8
Sep 9
as low as
$289
Chicago, US (CHI) - Santiago, DO (STI)

Aug 29
Aug 29
as low as
$352
Chicago, US (CHI) - Santiago, DO (STI)

Aug 29
Aug 29
as low as
$380
Chicago, US (CHI) - Santiago, DO (STI)

Aug 29
Aug 31
as low as
$434
Frequently Asked Questions
Flights to Santiago
- Flights
- Caribbean
- Dominican Republic
- Santiago
- Flights
- North America
- United States
- Illinois
- Chicago