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Santiago de los Caballeros

$174+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 12/53:26 pmORD - STI
1 stop9h 16mSpirit Airlines
Fri 12/123:43 amSTI - ORD
1 stop9h 25mSpirit Airlines
Deal found 11/3$335
This Expedia deal was found by Cheapflights users on 11/1. 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.
Tue 12/163:26 pmORD - STI
1 stop9h 16mSpirit Airlines
Mon 12/223:43 amSTI - ORD
1 stop16h 56mSpirit Airlines
Deal found 11/1$371
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/258:10 amORD - STI
1 stop12h 46mAmerican Airlines
Tue 12/26:20 amSTI - ORD
2 stops11h 36mAmerican Airlines
Deal found 11/3$398
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1610:00 amORD - STI
2 stops14h 42mMultiple Airlines
Mon 12/223:43 amSTI - ORD
1 stop13h 59mMultiple Airlines
Deal found 11/1$427
This Delta deal was found by Cheapflights users on 11/2. 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 11/37:00 amORD - STI
1 stop11h 06mDelta
Tue 11/112:31 pmSTI - ORD
1 stop8h 56mDelta
Deal found 11/2$446
This Delta deal was found by Cheapflights users on 11/2. 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.
Sun 11/24:56 pmORD - STI
2 stops25h 10mDelta
Tue 11/116:40 amSTI - ORD
1 stop13h 13mDelta
Deal found 11/2$450
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/45:00 amORD - STI
2 stops8h 33mAmerican Airlines
Sun 11/97:00 amSTI - ORD
1 stop11h 03mAmerican Airlines
Deal found 11/2$455
This Delta deal was found by Cheapflights users on 11/3. 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 11/259:34 amMDW - STI
2 stops13h 25mDelta
Fri 11/286:40 amSTI - MDW
2 stops13h 38mDelta
Deal found 11/3$2,808

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$334
(Cheapflightsfares)

One-way from

$174
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$478
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. 11% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Mon 1/19

8:50 am-9:46 pm

2 stops10h 56m

Santiago de los Caballeros

Wed 1/28

6:00 am-4:20 pm

1 stop12h 20m

$388

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/2

5:20 am-5:06 pm

2 stops33h 46m

Santiago de los Caballeros

Mon 2/9

6:18 pm-9:23 am

1 stop17h 05m

$390

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 4/3

6:26 pm-3:55 am

1 stop8h 29m

Santiago de los Caballeros

Mon 4/13

6:00 am-5:31 pm

1 stop12h 31m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 4/6

6:26 pm-3:55 am

1 stop8h 29m

Santiago de los Caballeros

Thu 4/9

6:00 am-5:31 pm

1 stop12h 31m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

7:00 am-8:39 pm

1 stop11h 39m

Santiago de los Caballeros

Thu 3/5

1:35 pm-9:33 pm

1 stop9h 58m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 12/25

7:41 pm-4:50 am

1 stop7h 09m

Santiago de los Caballeros

Sat 1/10

5:01 am-5:44 pm

1 stop14h 43m

$398

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/2

7:05 am-8:34 pm

2 stops11h 29m

Santiago de los Caballeros

Mon 2/9

6:39 am-9:04 pm

2 stops16h 25m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 3/1

7:00 am-12:53 am

2 stops15h 53m

Santiago de los Caballeros

Thu 3/5

6:35 am-5:37 pm

1 stop13h 02m

$402

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 12/5

1:34 pm-2:42 am

2 stops11h 08m

Santiago de los Caballeros

Fri 12/12

3:43 am-11:08 am

1 stop9h 25m

$403

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 4/10

1:45 pm-2:54 am

1 stop12h 09m

Santiago de los Caballeros

Sat 4/18

5:01 am-12:50 pm

1 stop8h 49m

$440

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 29 results
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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 November.
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, March is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $194). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $426). 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 November 3, 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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 47% 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 November 3, 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
7.9
Good
8,002 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
8,002 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
American Airlines
7.2
Good
11,038 reviews
Delta
7.9
Good
8,002 reviews

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

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 29m. American Airlines provides one of the quickest options available for as low as $398. 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 $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 Spirit Airlines and Delta - these airlines can fly you to your destination from $298 and $356, respectively. Users have found that United Airlines is 56% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Santiago de los Caballeros one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $181. Users have also found prices from $186 and $187 on American Airlines and United Airlines, respectively.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $194). Flying from Chicago to Santiago de los Caballeros in July is currently the most expensive (average of $426). 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

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$226Average$662FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$298Average$441FlexibilityNo cancel feeOn-time65%
DeltaCheapest$356Average$437FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$391Average$543FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$395Average$757FlexibilityNo cancel feeOn-time71%

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