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Santiago de los Caballeros

$162+ 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 28 — Feb 41
Tue 1/28
Tue 2/4
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 January 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$403
(Delta)

One-way from

$162
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$457
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. 10% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 23, 2025.

This Delta deal was found by Cheapflights users on 1/22. 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.
Wed 1/297:05 amORD - STI
1 stop9h 39mDelta
Tue 2/112:30 pmSTI - ORD
1 stop8h 54mDelta
Deal found 1/22$403
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/68:46 pmORD - STI
1 stop19h 37mMultiple Airlines
Sun 3/96:42 pmSTI - ORD
2 stops16h 02mMultiple Airlines
Deal found 1/22$408
This CheapOair deal was found by Cheapflights users on 1/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/64:45 pmMDW - STI
2 stops23h 38mFrontier
Sun 3/96:42 pmSTI - MDW
2 stops25h 53mFrontier
Deal found 1/22$411
This JetBlue deal was found by Cheapflights users on 1/22. 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.
Tue 3/411:44 amORD - STI
1 stop11h 44mJetBlue
Mon 3/245:12 amSTI - ORD
1 stop12h 18mJetBlue
Deal found 1/22$413
This American Airlines deal was found by Cheapflights users on 1/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/262:55 pmORD - STI
1 stop21h 03mAmerican Airlines
Tue 3/252:11 pmSTI - ORD
2 stops18h 01mAmerican Airlines
Deal found 1/22$417
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/182:29 pmORD - STI
1 stop17h 35mSpirit Airlines
Mon 3/310:59 amSTI - ORD
1 stop14h 59mSpirit Airlines
Deal found 1/22$419
This United Airlines deal was found by Cheapflights users on 1/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/14:08 pmORD - STI
1 stop8h 36mUnited Airlines
Fri 2/284:00 pmSTI - ORD
1 stop9h 09mUnited Airlines
Deal found 1/22$493
This Delta deal was found by Cheapflights users on 1/21. 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 3/410:57 amMDW - STI
2 stops12h 36mDelta
Tue 3/116:15 amSTI - MDW
2 stops12h 47mDelta
Deal found 1/21$540
This FlightHub deal was found by Cheapflights users on 1/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/95:27 pmORD - STI
2 stops22h 53mFrontier
Mon 4/146:40 pmSTI - ORD
2 stops25h 24mFrontier
Deal found 1/22$570

Find flights from Chicago to Santiago de los Caballeros within your budget

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 January 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 3/4

7:05 am-6:44 pm

1 stop9h 39m

Santiago de los Caballeros

Tue 3/11

1:27 pm-9:26 pm

1 stop8h 59m

$403

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 3/6

8:46 pm-6:23 pm

1 stop19h 37m

Santiago de los Caballeros

Sun 3/9

6:42 pm-9:44 am

2 stops16h 02m

$408

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 3/6

4:45 pm-6:23 pm

2 stops23h 38m

Santiago de los Caballeros

Sun 3/9

6:42 pm-7:35 pm

2 stops25h 53m

$411

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 3/4

11:44 am-1:28 am

1 stop11h 44m

Santiago de los Caballeros

Mon 3/24

5:12 am-4:30 pm

1 stop12h 18m

$413

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 2/26

2:55 pm-1:58 pm

1 stop21h 03m

Santiago de los Caballeros

Tue 3/25

2:11 pm-7:12 am

2 stops18h 01m

$417

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 2/18

2:29 pm-10:04 am

1 stop17h 35m

Santiago de los Caballeros

Mon 3/3

10:59 am-11:58 pm

1 stop14h 59m

$419

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sat 2/1

4:08 pm-2:44 am

1 stop8h 36m

Santiago de los Caballeros

Fri 2/28

4:00 pm-11:09 pm

1 stop9h 09m

$493

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Tue 3/4

10:57 am-1:33 am

2 stops12h 36m

Santiago de los Caballeros

Tue 3/11

6:15 am-6:02 pm

2 stops12h 47m

$540

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Wed 4/9

5:27 pm-5:20 pm

2 stops22h 53m

Santiago de los Caballeros

Mon 4/14

6:40 pm-7:04 pm

2 stops25h 24m

$570

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Sun 2/2

12:25 pm-5:29 pm

2 stops27h 04m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santiago de los Caballeros flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Chicago to Santiago de los Caballeros

Get recent, data-driven insights about flights from Chicago to Santiago de los Caballeros including ideal travel times, pricing trends, and more.

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 January 23, 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 January 23, 2025.
Read reviews from past customers who have flown Delta, Frontier and Spirit 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
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,514 reviews
Delta
8.0
Very good
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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

JetBlue
7.4
Good
3,190 reviews
Delta
8.0
Very good
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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

United Airlines
7.4
Good
8,975 reviews
Delta
8.0
Very good
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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

Spirit Airlines
6.3
Okay
8,111 reviews
Delta
8.0
Very good
8,514 reviews

Entertainment

7.9

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Reviews

1 / 10

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 $403, 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 Frontier and JetBlue - these airlines can fly you to your destination from $411 and $413, respectively. Users have found that Delta is 18% 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 $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 January 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$233Average$285FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$353Average$645FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$391Average$529FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$392Average$531FlexibilityNo cancel feeOn-time69%
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