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Santiago de los Caballeros

$164+ Cheap flights from Illinois 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — STI
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Illinois to Santiago de los Caballeros

Cheapest flights from Illinois to Santiago de los Caballeros
Explore the most affordable flight options available from Illinois to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 2/45:15 am
ORD
-
STI
1 stop8h 18m
Spirit Airlines
Sat 2/74:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/20$265
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:15 am
ORD
-
STI
1 stop8h 18m
Spirit Airlines
Wed 2/254:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/21$272
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:15 am
ORD
-
STI
1 stop8h 20m
Spirit Airlines
Fri 2/274:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/21$324
This Expedia deal was found by Cheapflights users on 1/19. 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.
Wed 2/115:15 am
ORD
-
STI
1 stop8h 18m
Spirit Airlines
Sun 2/154:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/19$334
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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.
Sat 2/147:00 am
ORD
-
STI
1 stop6h 35m
Spirit Airlines
Sat 2/284:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/18$344
This Expedia deal was found by Cheapflights users on 1/19. 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.
Wed 2/255:15 am
ORD
-
STI
1 stop8h 20m
Multiple Airlines
Mon 3/21:39 pm
STI
-
ORD
2 stops24h 15m
Multiple Airlines
Deal found 1/19$353
This Cheapflightsfares deal was found by Cheapflights users on 1/18. 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.
Thu 2/125:15 am
ORD
-
STI
1 stop8h 20m
Spirit Airlines
Sat 2/284:40 pm
STI
-
ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/18$365
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/258:16 pm
ORD
-
STI
1 stop17h 19m
Spirit Airlines
Mon 3/24:40 pm
STI
-
ORD
1 stop28h 31m
Spirit Airlines
Deal found 1/19$377
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Thu 5/286:30 am
STL
-
STI
1 stop7h 42m
United Airlines
Tue 6/22:07 pm
STI
-
STL
1 stop8h 48m
United Airlines
Deal found 1/20$539
This American Airlines deal was found by Cheapflights users on 1/19. 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 5/286:20 am
STL
-
STI
2 stops13h 41m
American Airlines
Tue 6/27:00 am
STI
-
STL
2 stops14h 26m
American Airlines
Deal found 1/19$543
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.
Thu 5/287:20 am
STL
-
STI
2 stops15h 54m
Delta
Tue 6/28:59 pm
STI
-
STL
2 stops16h 55m
Delta
Deal found 1/21$553
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/216:20 pm
STL
-
STI
1 stop17h 11m
American Airlines
Sat 2/282:31 pm
STI
-
STL
2 stops20h 24m
American Airlines
Deal found 1/19$566

Find flight deals from Illinois to Santiago de los Caballeros

Keep the following information in mind while searching for Illinois to Santiago de los Caballeros flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$249
(FlightHub)

One-way from

$164
(Expedia)

Popular in

December

Cheapest in

September

Average price

$461
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 Illinois to Santiago de los Caballeros
Search Deals
One-way flight from Illinois to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 21, 2026.
Use the filters below to find and compare flights from Illinois to Santiago de los Caballeros that are best for you.

Fly from

Illinois

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

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

$272

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

Sun 2/15

4:40 pm-11:47 pm

1 stop9h 07m

$334

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 2/20

5:15 am-3:35 pm

1 stop8h 20m

Santiago de los Caballeros

Fri 2/27

4:40 pm-7:54 am

2 stops17h 14m

$378

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

Mon 3/2

1:39 pm-11:54 am

2 stops24h 15m

$394

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Fri 2/27

3:40 pm-3:35 pm

1 stop21h 55m

Santiago de los Caballeros

Mon 3/2

4:40 pm-11:22 am

1 stop20h 42m

$399

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Thu 3/12

4:35 pm-1:49 am

1 stop8h 14m

Santiago de los Caballeros

Sat 3/14

2:46 am-6:21 pm

1 stop16h 35m

$405

ChicagoSantiago de los Caballeros

ORD - STI

ORDSTI

Chicago O'Hare Intl

Tue 5/26

7:30 am-7:20 pm

1 stop10h 50m

Santiago de los Caballeros

Thu 6/11

6:15 am-6:41 pm

2 stops13h 26m

$410

St. LouisSantiago de los Caballeros

STL - STI

STLSTI

Lambert-St Louis

Sat 2/21

1:36 pm-1:31 pm

2 stops21h 55m

Santiago de los Caballeros

Sat 2/28

2:31 pm-8:55 am

2 stops20h 24m

$553

St. LouisSantiago de los Caballeros

STL - STI

STLSTI

Lambert-St Louis

Sat 1/24

11:20 am-11:51 pm

2 stops10h 31m

Santiago de los Caballeros

Wed 1/28

6:00 am-10:58 pm

2 stops18h 58m

$768

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Fri 3/20

2:41 pm-8:00 am

2 stops16h 19m

Santiago de los Caballeros

Thu 3/26

9:13 am-3:14 pm

2 stops31h 01m

$782

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 28 results
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Best time to book a flight from Illinois to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from Illinois 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 Illinois to Santiago de los Caballeros

What is the cheapest month to book a flight from Illinois to Santiago de los Caballeros?

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

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois?

    Santiago de los Caballeros (STI) is the airport you will fly into if you book a flight from Illinois to Santiago de los Caballeros. It is only a 6.8 mi journey from Santiago (STI) to Santiago de los Caballeros’s city center.

  • How long is the flight from Illinois to Santiago de los Caballeros?

    Airlines like Spirit Airlines and American Airlines fly from Illinois to Santiago de los Caballeros in about 8h 18m. The time it takes to get you to your destination can typically vary by up to 13h 37m. The distance from Illinois to Santiago de los Caballeros is about 1858 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Illinois to Santiago de los Caballeros?

    The most popular flight routes from Illinois to Santiago de los Caballeros are Chicago O'Hare Intl - Santiago de los Caballeros, Chicago Midway - Santiago de los Caballeros and Lambert-St Louis - Santiago de los Caballeros.

  • Can I find deals for flights from Illinois to Santiago de los Caballeros that include hotel bookings?

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

  • How can I find direct flights from Illinois 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 Illinois to Santiago de los Caballeros.

  • Can I find deals for business class flights from Illinois to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Santiago de los Caballeros?

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

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Santiago de los Caballeros flights
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John F Kennedy Intl to Punta Cana flights
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Raleigh to Punta Cana flights
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Top 5 airlines flying from Illinois to Santiago de los Caballeros

Discover the top 5 airlines that operate flights from Illinois 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$215Average$677FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$255Average$472FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$298Average$441FlexibilityNo cancel feeOn-time65%
DeltaCheapest$356Average$422FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$395Average$757FlexibilityNo cancel feeOn-time71%

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