HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Santiago de los Caballeros

$140+ Cheap flights from Chicago (CHI) to Santiago de los Caballeros (STI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santiago de los Caballeros (STI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 21, 2025.

Round-trip from

$323
(FlightHub)

One-way from

$140
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$392
From Chicago (CHI) to Santiago de los Caballeros
Search Deals
One-way flight from Chicago (CHI) to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Chicago to Santiago de los Caballeros

Cheapest flights from Chicago to Santiago de los Caballeros
Explore the most affordable flight options available from Chicago to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:44 pmORD - STI
1 stop15h 19mSpirit Airlines
Mon 9/2212:10 pmSTI - ORD
1 stop11h 38mSpirit Airlines
Deal found 8/21$325
This Cheapflightsfares deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:44 pmORD - STI
1 stop15h 19mSpirit Airlines
Fri 9/2612:10 pmSTI - ORD
1 stop11h 38mSpirit Airlines
Deal found 8/20$326
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/64:51 pmORD - STI
1 stop16h 47mSpirit Airlines
Wed 10/811:43 amSTI - ORD
1 stop7h 53mSpirit Airlines
Deal found 8/21$327
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/54:51 pmORD - STI
1 stop16h 47mSpirit Airlines
Sat 10/2511:43 amSTI - ORD
1 stop13h 02mSpirit Airlines
Deal found 8/20$330
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:41 pmORD - STI
1 stop13h 57mSpirit Airlines
Sun 11/212:43 pmSTI - ORD
1 stop14h 20mSpirit Airlines
Deal found 8/20$341
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:41 pmORD - STI
1 stop13h 57mSpirit Airlines
Sun 10/2611:43 amSTI - ORD
1 stop14h 20mSpirit Airlines
Deal found 8/21$342
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/215:05 amORD - STI
1 stop28h 58mSpirit Airlines
Sat 9/2712:10 pmSTI - ORD
1 stop11h 38mSpirit Airlines
Deal found 8/20$346
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:44 pmORD - STI
1 stop15h 19mSpirit Airlines
Fri 10/1011:43 amSTI - ORD
1 stop13h 02mSpirit Airlines
Deal found 8/21$350
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/67:41 pmORD - STI
1 stop13h 57mSpirit Airlines
Mon 10/1311:43 amSTI - ORD
1 stop13h 02mSpirit Airlines
Deal found 8/21$363
This FlightHub deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:22 pmORD - STI
2 stops18h 16mSpirit Airlines
Mon 10/2011:43 amSTI - ORD
1 stop13h 02mSpirit Airlines
Deal found 8/21$372
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/69:35 amMDW - STI
2 stops13h 49mDelta
Mon 10/138:31 pmSTI - MDW
2 stops16h 57mDelta
Deal found 8/21$727
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1910:35 amMDW - STI
2 stops12h 59mDelta
Fri 9/266:11 amSTI - MDW
2 stops13h 24mDelta
Deal found 8/20$1,928

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Santiago de los Caballeros that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Chicago to Santiago de los Caballeros that are best for you.

Fly from

Chicago

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 9/19

6:44 pm-11:03 am

1 stop15h 19m

Santiago de los Caballeros

Tue 9/23

12:10 pm-10:48 pm

1 stop11h 38m

$325

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 9/19

6:44 pm-11:03 am

1 stop15h 19m

Santiago de los Caballeros

Mon 9/22

12:10 pm-10:48 pm

1 stop11h 38m

$325

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 9/19

6:44 pm-11:03 am

1 stop15h 19m

Santiago de los Caballeros

Fri 9/26

12:10 pm-10:48 pm

1 stop11h 38m

$326

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/15

7:41 pm-10:38 am

1 stop13h 57m

Santiago de los Caballeros

Mon 10/20

11:43 am-6:36 pm

1 stop7h 53m

$327

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 10/6

4:51 pm-10:38 am

1 stop16h 47m

Santiago de los Caballeros

Wed 10/8

11:43 am-6:36 pm

1 stop7h 53m

$327

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 10/5

4:51 pm-10:38 am

1 stop16h 47m

Santiago de los Caballeros

Sat 10/25

11:43 am-11:45 pm

1 stop13h 02m

$330

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 10/30

7:41 pm-10:38 am

1 stop13h 57m

Santiago de los Caballeros

Sun 11/2

12:43 pm-1:03 am

1 stop14h 20m

$341

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 10/22

7:41 pm-10:38 am

1 stop13h 57m

Santiago de los Caballeros

Sun 10/26

11:43 am-1:03 am

1 stop14h 20m

$342

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 9/21

5:05 am-11:03 am

1 stop28h 58m

Santiago de los Caballeros

Sat 9/27

12:10 pm-10:48 pm

1 stop11h 38m

$346

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:03 am

1 stop15h 19m

Santiago de los Caballeros

Fri 10/10

11:43 am-11:45 pm

1 stop13h 02m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 26 results
1
2
3

Best time to book a flight from Chicago to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from Chicago 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Santiago de los Caballeros

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

Currently, May is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $347). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $600). 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.

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

Find hourly flight availability from Chicago to Santiago de los Caballeros. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2025.

One of the essential ways to save on airfare from Chicago to Santiago de los Caballeros is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% on airfare.

Reviews of airlines servicing Santiago de los Caballeros

Get insights into the airlines that provide service to Santiago de los Caballeros. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Santiago de los Caballeros. Reviews last updated August 21, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago 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
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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!
United Airlines
7.4
Good
8,930 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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!
JetBlue
7.2
Good
2,916 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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!
Spirit Airlines
6.3
Okay
8,035 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

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

Find useful and relevant information for your journey from Chicago 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?

    For a flight from Chicago to Santiago de los Caballeros, you will be flying into Santiago. Santiago de los Caballeros (STI) is just 6.8 mi from the center of the city. Santiago is the only Santiago de los Caballeros airport and it handles 0 inbound flights from Chicago per day. 4 airlines have flights to Santiago de los Caballeros from Chicago on a regular basis.

  • How long is the flight from Chicago to Santiago de los Caballeros?

    A quick flight from Chicago to Santiago de los Caballeros can take about 13h 49m. Spirit Airlines provides one of the quickest options available for as low as $727. Chicago and Santiago de los Caballeros are separated by a distance of 1843 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Santiago de los Caballeros round-trip?

    Currently priced at $226, United Airlines will fly you from Chicago to Santiago de los Caballeros and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and JetBlue - these airlines can fly you to your destination from $345 and $391, respectively. Users have found that United Airlines is 56% cheaper than the other options available to this destination.

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

    Yes. In addition to deals on Chicago to Santiago de los Caballeros flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago 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 Chicago to Santiago de los Caballeros.

  • Can I find deals for business class flights from Chicago to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Chicago 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 to Santiago de los Caballeros?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $347). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $600). 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.

See more FAQs

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.

Top 4 airlines flying from Chicago to Santiago de los Caballeros

Discover the top 4 airlines that operate flights from Chicago to Santiago de los Caballeros. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$226Average$723FlexibilityNo cancel feeOn-time69%
DeltaCheapest$345Average$437FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$391Average$472FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$741FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.