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Santiago de los Caballeros

$185+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$393
(Delta)

One-way from

$185
(Delta)

Popular in

December

Cheapest in

September

Average price

$526
Provider with most accurate pricing for Chicago (CHI)-Santiago de los Caballeros flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Santiago de los Caballeros flights.
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From Chicago (CHI) to Santiago de los Caballeros
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One-way flight from Chicago (CHI) to Santiago de los Caballeros
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Highest demand for flights based on searches. 8% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 17, 2025.

This Delta deal was found by Cheapflights users on 4/16. 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 5/57:10 amORD - STI
1 stop10h 31mDelta
Fri 5/96:11 amSTI - ORD
1 stop12h 18mDelta
Deal found 4/16$393
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:05 amORD - STI
1 stop8h 43mSpirit Airlines
Sun 5/113:53 pmSTI - ORD
1 stop9h 12mSpirit Airlines
Deal found 4/17$396
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Thu 5/83:15 pmORD - STI
1 stop22h 45mAmerican Airlines
Wed 5/143:50 pmSTI - ORD
1 stop7h 58mAmerican Airlines
Deal found 4/16$418
This JetBlue deal was found by Cheapflights users on 4/16. 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.
Sat 5/174:03 pmORD - STI
1 stop9h 44mJetBlue
Wed 5/288:45 amSTI - ORD
1 stop14h 09mJetBlue
Deal found 4/16$423
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/1712:41 pmORD - STI
1 stop25h 07mMultiple Airlines
Fri 5/303:20 pmSTI - ORD
2 stops18h 30mMultiple Airlines
Deal found 4/17$482
This Delta deal was found by Cheapflights users on 4/16. 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 5/59:52 amMDW - STI
2 stops13h 35mDelta
Fri 5/96:11 amSTI - MDW
2 stops16h 17mDelta
Deal found 4/16$577

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 April 17, 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 5/5

7:10 am-6:41 pm

1 stop10h 31m

Santiago de los Caballeros

Fri 5/9

6:11 am-5:29 pm

1 stop12h 18m

$393

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 5/8

5:05 am-2:48 pm

1 stop8h 43m

Santiago de los Caballeros

Sun 5/11

3:53 pm-12:05 am

1 stop9h 12m

$396

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 5/8

3:15 pm-3:00 pm

1 stop22h 45m

Santiago de los Caballeros

Wed 5/14

3:50 pm-10:48 pm

1 stop7h 58m

$418

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 5/17

4:03 pm-2:47 am

1 stop9h 44m

Santiago de los Caballeros

Wed 5/28

8:45 am-9:54 pm

1 stop14h 09m

$423

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 5/17

12:41 pm-2:48 pm

1 stop25h 07m

Santiago de los Caballeros

Fri 5/30

3:20 pm-8:50 am

2 stops18h 30m

$482

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 5/5

9:52 am-12:27 am

2 stops13h 35m

Santiago de los Caballeros

Fri 5/9

6:11 am-9:28 pm

2 stops16h 17m

$577

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 4/23

1:50 pm-12:27 am

1 stop9h 37m

$185

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 4/26

11:45 am-2:46 pm

2 stops26h 01m

$325

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 4/26

10:22 am-2:46 pm

3 stops27h 24m

$356

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 4/22

6:30 pm-2:26 pm

2 stops18h 56m

$461

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 11 results
1
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice Accuracy3 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-Santiago de los Caballeros flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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, 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 $631). 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 April 17, 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.

Rainfall in Santiago de los Caballeros by month

Plan your trip to Santiago de los Caballeros by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Santiago de los Caballeros ranges from 3.0 - 11.6 inches per month. December is typically the wettest month, when rainfall can reach 11.6 in. July is typically the driest time to visit Santiago de los Caballeros when rainfall is around 3.0 in.

Temperature in Santiago de los Caballeros by month

Plan your trip to Santiago de los Caballeros by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Santiago de los Caballeros, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 April 17, 2025.
Read reviews from past customers who have flown Delta, JetBlue and American Airlines from Chicago to Santiago de los Caballeros. 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
7,917 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,917 reviews
Delta
8.0
Very good
7,917 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,926 reviews
Delta
8.0
Very good
7,917 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,917 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Spirit Airlines
6.3
Okay
7,926 reviews
Delta
8.0
Very good
7,917 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    Currently priced at $393, Delta will fly you from Chicago to Santiago de los Caballeros and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and JetBlue - these airlines can fly you to your destination from $396 and $423, respectively. Users have found that Delta is 28% 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 Delta. According to our data, you can fly for as low as $185. Users have also found prices from $217 and $461 on Spirit Airlines and American 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, 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 $631). 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 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$226Average$662FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$343Average$472FlexibilityNo cancel feeOn-time62%
DeltaCheapest$345Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$437Average$765FlexibilityNo cancel feeOn-time71%

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