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

$117+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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

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 December 23, 2025.

This JetBlue deal was found by Cheapflights users on 12/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:41 pmORD - STI
1 stop7h 09mJetBlue
Sat 1/105:01 amSTI - ORD
1 stop14h 42mJetBlue
Deal found 12/21$859
This Delta deal was found by Cheapflights users on 12/21. 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.
Thu 12/258:00 amORD - STI
1 stop16h 51mDelta
Wed 1/79:59 pmSTI - ORD
1 stop13h 50mDelta
Deal found 12/21$958
This KAYAK deal was found by Cheapflights users on 12/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:34 pmORD - STI
2 stops11h 08mSpirit Airlines
Sat 1/104:40 pmSTI - ORD
2 stops18h 32mSpirit Airlines
Deal found 12/21$983
This JetBlue deal was found by Cheapflights users on 12/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:41 pmORD - STI
1 stop7h 09mJetBlue
Wed 1/76:01 amSTI - ORD
1 stop15h 35mJetBlue
Deal found 12/22$1,055
This KAYAK deal was found by Cheapflights users on 12/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:34 pmORD - STI
2 stops11h 08mSpirit Airlines
Tue 1/63:43 amSTI - ORD
2 stops17h 19mSpirit Airlines
Deal found 12/21$1,137
This Delta deal was found by Cheapflights users on 12/22. 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.
Thu 12/259:41 amORD - STI
2 stops15h 10mDelta
Sat 1/106:38 amSTI - ORD
2 stops13h 16mDelta
Deal found 12/22$1,235
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:37 pmORD - STI
1 stop7h 14mUnited Airlines
Wed 12/244:00 pmSTI - ORD
1 stop9h 35mUnited Airlines
Deal found 12/21$1,322
This Delta deal was found by Cheapflights users on 12/21. 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.
Tue 12/235:30 amORD - STI
2 stops11h 47mDelta
Wed 12/248:45 pmSTI - ORD
1 stop17h 07mDelta
Deal found 12/21$1,496
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:11 amORD - STI
2 stops11h 53mAmerican Airlines
Wed 12/246:57 amSTI - ORD
2 stops13h 48mAmerican Airlines
Deal found 12/21$1,643

Find 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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$240
(Cheapflightsfares)

One-way from

$117
(Super.com)

Popular in

December

Cheapest in

September

Average price

$915
Provider with most accurate pricing for Chicago (CHI)-Santiago de los Caballeros flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Santiago de los Caballeros flights.
Search Deals
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. 17% potential increase in price ($112 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 23, 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

Wed 2/4

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Sat 2/7

4:40 pm-11:47 pm

1 stop9h 07m

$240

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 2/10

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Tue 2/24

4:40 pm-11:47 pm

1 stop9h 07m

$257

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/11

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Wed 2/25

4:40 pm-11:47 pm

1 stop9h 07m

$261

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/9

7:20 am-3:33 pm

1 stop6h 13m

Santiago de los Caballeros

Mon 2/23

4:40 pm-11:47 pm

1 stop9h 07m

$268

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/16

7:00 am-3:35 pm

1 stop6h 35m

Santiago de los Caballeros

Mon 3/2

4:40 pm-11:47 pm

1 stop9h 07m

$306

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 2/8

8:43 pm-3:33 pm

1 stop16h 50m

Santiago de los Caballeros

Sun 2/22

4:40 pm-11:47 pm

1 stop9h 07m

$310

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/4

12:44 pm-3:33 pm

3 stops24h 49m

Santiago de los Caballeros

Wed 2/11

4:40 pm-11:47 pm

1 stop9h 07m

$320

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/12

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Fri 1/16

4:40 pm-5:52 pm

2 stops27h 12m

$328

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Wed 1/14

6:14 pm-12:50 am

2 stops28h 36m

Santiago de los Caballeros

Wed 3/25

6:33 am-4:55 pm

2 stops11h 22m

$449

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 1/19

6:00 am-12:50 am

2 stops16h 50m

Santiago de los Caballeros

Mon 1/26

6:39 am-10:22 pm

2 stops17h 43m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 32 results
1
2
3
4

Compare providers for flights from Chicago to Santiago de los Caballeros

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Santiago de los Caballeros in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Santiago de los Caballeros flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Santiago de los Caballeros flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Santiago de los Caballeros flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Santiago de los Caballeros flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Santiago de los Caballeros flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, November is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $206). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $425). 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.

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 December 23, 2025.
Peruse reviews from past customers who have flown with 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.
United Airlines
7.4
Good
9,105 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,105 reviews
United Airlines
7.4
Good
9,105 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
American Airlines
7.2
Good
11,054 reviews
United Airlines
7.4
Good
9,105 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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. 5 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 8h 18m. Spirit Airlines provides one of the quickest options available for as low as $240. Chicago and Santiago de los Caballeros are separated by a distance of 1858 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 $215, 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 JetBlue and Spirit Airlines - these airlines can fly you to your destination from $255 and $298, respectively. Users have found that United Airlines is 58% 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, November is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $206). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $425). 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 5 airlines flying from Chicago to Santiago de los Caballeros

Discover the top 5 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$662FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$255Average$472FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$298Average$441FlexibilityNo cancel feeOn-time65%
DeltaCheapest$356Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$437Average$772FlexibilityNo 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.