
Flight Deals from Santiago to Chicago from $178
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
Stops
- Up to 1 stop$333
- Up to 2 stops$554
Airlines
- American Airlines$549
- JetBlue$597
- Spirit Airlines$333
- United Airlines$576
Cabin Class
- Economy$333
Departure Airports
- Cibao International Airport$333
Arrival Airports
- Chicago O Hare Airport$333
Layover Airports
- Charlotte Douglas International Airport$554
- Fort Lauderdale Hollywood International Airport$333
- General Edward Lawrence Logan International Airport$597
- Miami International Airport$549
- New York John F Kennedy Airport$597
- Newark Liberty Airport$576
- Reagan Washington National Airport$554
Best Price. GUARANTEED.
Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/10/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/17/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/18/25

09/10/25
09/11/25

09/17/25
09/18/25
Top Deals on flights from Santiago to Chicago
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 11
as low as
$178
Santiago, DO (STI) - Chicago, US (CHI)

Oct 21
Oct 21
as low as
$243
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 11
as low as
$287
Santiago, DO (STI) - Chicago, US (CHI)

Aug 22
Aug 22
as low as
$289
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 11
as low as
$291
Santiago, DO (STI) - Chicago, US (CHI)

Oct 21
Oct 21
as low as
$294
Santiago, DO (STI) - Chicago, US (CHI)

Oct 21
Oct 21
as low as
$298
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 12
as low as
$387
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 11
as low as
$411
Santiago, DO (STI) - Chicago, US (CHI)

Sep 11
Sep 11
as low as
$418
Frequently Asked Questions
Flights to Chicago
- Flights
- North America
- United States
- Illinois
- Chicago
- Flights
- Caribbean
- Dominican Republic
- Santiago