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Santiago de los Caballeros

$261+ Cheap flights from O'Hare Intl (ORD) 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — STI
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Santiago de los Caballeros

Cheapest flights from O'Hare Intl to Santiago de los Caballeros
Explore the most affordable flight options available from O'Hare Intl to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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.
Tue 12/93:26 pmORD - STI
1 stop9h 16mSpirit Airlines
Tue 12/163:43 amSTI - ORD
1 stop9h 25mSpirit Airlines
Deal found 12/3$391
This Mytrip deal was found by Cheapflights users on 12/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:26 pmORD - STI
1 stop9h 16mSpirit Airlines
Sat 1/174:40 pmSTI - ORD
1 stop9h 06mSpirit Airlines
Deal found 12/3$396
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/305:00 amORD - STI
1 stop19h 42mSpirit Airlines
Sun 1/254:40 pmSTI - ORD
1 stop20h 42mSpirit Airlines
Deal found 12/4$412
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/306:00 amORD - STI
2 stops18h 42mMultiple Airlines
Sun 1/254:40 pmSTI - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/4$413
This Expedia deal was found by Cheapflights users on 12/4. 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 12/87:00 amORD - STI
2 stops30h 47mJetBlue
Thu 12/114:57 pmSTI - ORD
2 stops30h 55mJetBlue
Deal found 12/4$414
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:00 amORD - STI
2 stops16h 42mMultiple Airlines
Sat 1/174:40 pmSTI - ORD
1 stop9h 06mMultiple Airlines
Deal found 12/3$421
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Sun 12/73:20 pmORD - STI
1 stop9h 22mMultiple Airlines
Wed 12/103:43 amSTI - ORD
1 stop22h 26mMultiple Airlines
Deal found 12/1$424
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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.
Wed 12/103:26 pmORD - STI
1 stop9h 16mSpirit Airlines
Sat 12/133:43 amSTI - ORD
1 stop9h 25mSpirit Airlines
Deal found 12/3$442
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Sun 12/79:14 pmORD - STI
2 stops27h 28mSpirit Airlines
Wed 12/103:43 amSTI - ORD
1 stop9h 25mSpirit Airlines
Deal found 12/1$443
This American Airlines deal was found by Cheapflights users on 12/4. 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.
Mon 12/810:14 amORD - STI
1 stop8h 19mAmerican Airlines
Wed 12/104:32 pmSTI - ORD
1 stop10h 05mAmerican Airlines
Deal found 12/4$446
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Sat 12/66:50 amORD - STI
2 stops11h 43mAmerican Airlines
Sat 12/134:32 pmSTI - ORD
1 stop10h 05mAmerican Airlines
Deal found 12/3$450

Find flight deals from O'Hare Intl to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$261
(Cheapflightsfares)

One-way from

$261
(Super.com)

Popular in

May

Cheapest in

October

Average price

$716
Provider with most accurate pricing for Chicago O'Hare Intl-Santiago de los Caballeros flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Santiago de los Caballeros flights.
Search Deals
From Chicago O'Hare Intl to Santiago de los Caballeros
Search Deals
One-way flight from Chicago O'Hare Intl to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($136 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($31 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 O'Hare Intl 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 4, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Santiago de los Caballeros that are best for you.

Fly from

O'Hare Intl

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 1/26

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Thu 1/29

4:40 pm-11:46 pm

1 stop9h 06m

$261

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Mon 2/16

5:15 am-3:35 pm

1 stop8h 20m

Santiago de los Caballeros

Mon 3/2

4:40 pm-12:18 am

1 stop9h 38m

$320

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 1/27

9:40 am-5:04 pm

2 stops29h 24m

Santiago de los Caballeros

Tue 2/24

4:40 pm-12:18 am

1 stop9h 38m

$331

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 1/14

5:15 am-3:33 pm

1 stop8h 18m

Santiago de los Caballeros

Mon 1/19

4:40 pm-1:57 pm

2 stops23h 17m

$349

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 2/27

5:15 am-3:35 pm

1 stop8h 20m

Santiago de los Caballeros

Sun 3/1

4:40 pm-12:18 am

1 stop9h 38m

$385

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 2/27

12:41 pm-12:27 pm

2 stops21h 46m

Santiago de los Caballeros

Sun 3/1

9:29 am-11:48 am

2 stops28h 19m

$387

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 2/5

7:01 am-8:34 pm

1 stop11h 33m

Santiago de los Caballeros

Mon 2/9

6:39 am-6:49 pm

2 stops14h 10m

$389

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 12/9

3:26 pm-2:42 am

1 stop9h 16m

Santiago de los Caballeros

Tue 12/16

3:43 am-11:08 am

1 stop9h 25m

$391

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 12/10

3:26 pm-2:42 am

1 stop9h 16m

Santiago de los Caballeros

Sat 1/17

4:40 pm-11:46 pm

1 stop9h 06m

$396

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 12/28

3:26 pm-2:42 am

1 stop9h 16m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 20 results
1
2

Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Santiago de los Caballeros in December.
ProviderPrice AccuracyTrust Score*
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 O'Hare Intl Airport-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 O'Hare Intl Airport-Santiago de los Caballeros flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Santiago de los Caballeros flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-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 O'Hare Intl Airport-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 O'Hare Intl to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from O'Hare Intl 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 O'Hare Intl Airport to Santiago de los Caballeros

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros?

Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros (average of $206). Flying from Chicago O'Hare Intl Airport 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.

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

Find hourly flight availability from O'Hare Intl 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 December 4, 2025.

When flying from Chicago O'Hare Intl Airport to Santiago de los Caballeros, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 66% versus a flight in the evening.

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 4, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Santiago de los Caballeros. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,066 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,899 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,157 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Overall

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl?

    Santiago de los Caballeros (STI), located 6.8 mi from the city center, is the airport you fly into when you book flights from Chicago O'Hare Intl to Santiago de los Caballeros. 5 airlines have flights to Santiago from Chicago O'Hare Intl on a regular basis. Booking flights from Chicago O'Hare Intl to Santiago de los Caballeros should not be difficult; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day.

  • How long is the flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros?

    There are many flights that can get you from Chicago O'Hare Intl Airport to Santiago de los Caballeros in 8h 18m. Fly via Spirit Airlines to get the fastest option. The distance between Chicago O'Hare Intl Airport and Santiago de los Caballeros is about 1858 mi.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Santiago de los Caballeros round-trip?

    Our cheapest airline available from Chicago O'Hare Intl Airport to Santiago de los Caballeros is United Airlines. Our recent data shows that you can find tickets from as low as $215 on this airline. Additional options worth looking into are Spirit Airlines and Delta, starting at $298 and $356 round-trip. United Airlines is currently priced 62% below the average price you’ll pay for this route.

  • Can I find deals for flights from O'Hare Intl to Santiago de los Caballeros that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl 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 O'Hare Intl to Santiago de los Caballeros.

  • Can I find deals for business class flights from O'Hare Intl to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Santiago de los Caballeros?

    Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Santiago de los Caballeros (average of $206). Flying from Chicago O'Hare Intl Airport 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

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Alternative routes for O'Hare Intl to Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Punta Cana flights
Midway to Punta Cana flights
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O'Hare Intl to Santo Domingo flights
Midway to Santo Domingo flights
Midway to Santiago de los Caballeros flights

Top 5 airlines flying from O'Hare Intl to Santiago de los Caballeros

Discover the top 5 airlines that operate flights from O'Hare Intl 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$554FlexibilityNo 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$437Average$772FlexibilityNo cancel feeOn-time71%

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