$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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Sep 29 — Oct 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Santiago de los Caballeros with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Santiago de los Caballeros
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Best
Last-minute
One-way
Cheapest flights from Chicago to Santiago de los CaballerosExplore 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 August 30, 2026.
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 August 30, 2026.
This FlightHub deal was found by Cheapflights users on 8/30. 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.
Fri 10/94:41 pm -
1 stop16h 47m
Sat 10/1711:43 am -
1 stop11h 56m
Deal found 8/30![Frontier logo]()
$384
This Delta deal was found by Cheapflights users on 8/27. 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 10/286:10 am -
1 stop10h 23m
Tue 11/109:25 pm -
1 stop14h 02m
Deal found 8/27![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 8/27. 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 10/286:04 am -
2 stops10h 29m
Tue 11/107:00 am -
2 stops11h 18m
Deal found 8/27![Delta logo]()
$431
This American Airlines deal was found by Cheapflights users on 8/25. 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 10/55:29 pm -
1 stop19h 43m
Wed 10/143:12 pm -
1 stop25h 19m
Deal found 8/25![American Airlines logo]()
$435
This Cheapflightsfares deal was found by Cheapflights users on 8/30. 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 9/256:00 am -
1 stop6h 27m
Fri 10/23:30 pm -
1 stop8h 38m
Deal found 8/30![JetBlue logo]()
$489
This JetBlue deal was found by Cheapflights users on 8/29. 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 10/207:00 am -
1 stop6h 47m
Fri 10/233:57 pm -
1 stop8h 33m
Deal found 8/29![JetBlue logo]()
$498
This Cheapflightsfares deal was found by Cheapflights users on 8/29. 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.
Mon 11/27:00 am -
1 stop6h 33m
Mon 11/94:43 pm -
1 stop9h 01m
Deal found 8/29![JetBlue logo]()
$517
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/259:01 pm -
2 stops16h 14m
Fri 10/23:15 pm -
1 stop10h 18m
Deal found 8/26![American Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 8/29. 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 11/26:10 am -
1 stop10h 23m
Mon 11/99:25 pm -
2 stops15h 14m
Deal found 8/29![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 8/27. 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 10/76:04 am -
2 stops10h 29m
Mon 10/127:05 pm -
2 stops17h 49m
Deal found 8/27![Delta logo]()
$1,571
This Delta deal was found by Cheapflights users on 8/28. 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 10/116:04 am -
2 stops10h 29m
Mon 10/127:05 pm -
2 stops22h 09m
Deal found 8/28![Delta logo]()
$1,748
This Delta deal was found by Cheapflights users on 8/29. 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.
Fri 11/136:00 am -
2 stops11h 59m
Mon 11/237:00 am -
2 stops13h 04m
Deal found 8/29![Delta logo]()
$2,080
Best flights from Chicago to Santiago de los CaballerosDiscover carefully curated flight deals from Chicago to Santiago de los Caballeros that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
Discover carefully curated flight deals from Chicago to Santiago de los Caballeros that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
This Delta deal was found by Cheapflights users on 8/28. 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 10/286:10 am -
1 stop10h 23m
Tue 11/109:25 pm -
1 stop14h 02m
Deal found 8/28![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 8/25. 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 10/55:29 pm -
1 stop19h 43m
Wed 10/143:12 pm -
1 stop25h 19m
Deal found 8/25![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 8/29. 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 10/286:04 am -
2 stops10h 29m
Tue 11/107:00 am -
2 stops13h 04m
Deal found 8/29![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 8/30. 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 11/106:00 am -
1 stop11h 59m
Wed 12/99:25 pm -
2 stops16h 55m
Deal found 8/30![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 8/27. 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 10/76:04 am -
2 stops10h 29m
Mon 10/127:05 pm -
2 stops17h 49m
Deal found 8/27![Delta logo]()
$1,571
This Delta deal was found by Cheapflights users on 8/29. 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.
Fri 11/136:00 am -
2 stops11h 59m
Mon 11/237:00 am -
2 stops13h 04m
Deal found 8/29![Delta logo]()
$2,080
This Delta deal was found by Cheapflights users on 8/28. 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 10/126:04 am -
2 stops10h 29m
Mon 10/197:05 pm -
2 stops17h 49m
Deal found 8/28![Delta logo]()
$2,531
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 10/106:04 am -
2 stops10h 29m
Sat 10/177:05 pm -
2 stops17h 49m
Deal found 8/28![Delta logo]()
$4,335
This Delta deal was found by Cheapflights users on 8/27. 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 10/116:04 am -
2 stops10h 29m
Sun 10/187:05 pm -
2 stops22h 42m
Deal found 8/27![Delta logo]()
$4,631
Last-minute flights from Chicago to Santiago de los CaballerosDiscover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated August 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 8/286:59 am -
1 stop6h 36m
Thu 9/33:35 pm -
1 stop7h 56m
Deal found 8/28![American Airlines logo]()
$824
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 8/289:59 am -
2 stops14h 56m
Thu 9/36:00 am -
2 stops17h 36m
Deal found 8/28![Delta logo]()
$6,335
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/179:01 pm -
2 stops16h 14m
Sun 9/203:15 pm -
1 stop10h 18m
Deal found 8/28![American Airlines logo]()
$762
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 9/186:59 am -
1 stop6h 16m
Fri 9/253:15 pm -
1 stop9h 15m
Deal found 8/27![American Airlines logo]()
$594
This Cheapflightsfares deal was found by Cheapflights users on 8/30. 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 9/256:00 am -
1 stop6h 27m
Fri 10/23:30 pm -
1 stop8h 38m
Deal found 8/30![JetBlue logo]()
$489
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/259:01 pm -
2 stops16h 14m
Fri 10/23:15 pm -
1 stop10h 18m
Deal found 8/26![American Airlines logo]()
$519
This JetBlue deal was found by Cheapflights users on 8/27. 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.
Mon 9/286:00 am -
1 stop6h 27m
Fri 10/23:30 pm -
1 stop8h 38m
Deal found 8/27![JetBlue logo]()
$529
One-way flights from Chicago to Santiago de los CaballerosSearch for one-way flight options from Chicago to Santiago de los Caballeros. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
Search for one-way flight options from Chicago to Santiago de los Caballeros. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This Priceline deal was found by Cheapflights users on 8/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:41 pm -
1 stop16h 47m
Deal found 8/29![Frontier logo]()
$174
This Delta deal was found by Cheapflights users on 8/28. 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 10/286:04 am -
2 stops10h 29m
Deal found 8/28![Delta logo]()
$196
This Delta deal was found by Cheapflights users on 8/28. 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 10/287:00 am -
2 stops9h 33m
Deal found 8/28![Delta logo]()
$196
This Delta deal was found by Cheapflights users on 8/29. 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 9/2810:48 am -
2 stops24h 38m
Deal found 8/29![Delta logo]()
$202
This JetBlue deal was found by Cheapflights users on 8/29. 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.
Sun 9/276:00 am -
1 stop6h 27m
Deal found 8/29![JetBlue logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 8/26. 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 9/256:00 am -
1 stop6h 27m
Deal found 8/26![JetBlue logo]()
$254
This Delta deal was found by Cheapflights users on 8/29. 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 9/295:30 am -
2 stops11h 29m
Deal found 8/29![Delta logo]()
$258
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sun 10/116:14 am -
1 stop6h 58m
Deal found 8/27![American Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 10/106:10 am -
1 stop10h 23m
Deal found 8/28![Delta logo]()
$284
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 9/259:01 pm -
2 stops16h 14m
Deal found 8/26![American Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Fri 9/253:50 pm -
3 stops22h 08m
Deal found 8/26![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/106:46 pm -
3 stops43h 12m
Deal found 8/26![Multiple Airlines logo]()
$381
Find 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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $384 (FlightHub) |
One-way from | $174 (Priceline) |
Popular in | December |
Cheapest in | February |
Average price | $827 |
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 7,457,451 searches. Data last updated August 30, 2026.
Use the filters below to find and compare flights from Chicago to Santiago de los Caballeros that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Wed 10/28
6:10 am-5:33 pm
1 stop10h 23m
Santiago de los Caballeros
Tue 11/10
9:25 pm-9:27 am
1 stop14h 02m
$426
Quickest round-trip
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Wed 10/28
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Tue 11/10
7:00 am-6:04 pm
2 stops13h 04m
$431
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Tue 11/10
6:00 am-7:59 pm
1 stop11h 59m
Santiago de los Caballeros
Wed 12/9
9:25 pm-12:20 pm
2 stops16h 55m
$431
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Mon 10/5
5:29 pm-2:12 pm
1 stop19h 43m
Santiago de los Caballeros
Wed 10/14
3:12 pm-3:31 pm
1 stop25h 19m
$435
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Wed 10/7
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Mon 10/12
7:05 pm-11:54 am
2 stops17h 49m
$1,571
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Fri 11/13
6:00 am-7:59 pm
2 stops11h 59m
Santiago de los Caballeros
Mon 11/23
7:00 am-6:04 pm
2 stops13h 04m
$2,080
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Mon 10/12
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Mon 10/19
7:05 pm-11:54 am
2 stops17h 49m
$2,531
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Sat 10/10
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Sat 10/17
7:05 pm-11:54 am
2 stops17h 49m
$4,335
ChicagoSantiago de los Caballeros
MDW Chicago Midway - STI Santiago de los Caballeros
MDWSTI
Chicago Midway
Sun 10/11
6:04 am-5:33 pm
2 stops10h 29m
Santiago de los Caballeros
Sun 10/18
7:05 pm-4:47 pm
2 stops22h 42m
$4,631
Cheapest one-way
ChicagoSantiago de los Caballeros
ORD Chicago O'Hare Intl - STI Santiago de los Caballeros
ORDSTI
Chicago O'Hare Intl
Fri 10/9
4:41 pm-10:28 am
1 stop16h 47m
$175
Showing 1-10 of 17 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
CHI-STI
ORD-STI
MDW-STI
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
CHI-STI
ORD-STI
MDW-STI
What is the cheapest month to book a flight from Chicago to Santiago de los Caballeros?
Currently, February is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $392). Flying from Chicago to Santiago de los Caballeros in December is currently the most expensive (average of $750). 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.
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 August 30, 2026.
Peruse reviews from past customers who have flown with 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.
Crew
7.9
Entertainment
6.8
Comfort
7.2
Overall
7.1
Boarding
7.5
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Crew
7.9
Entertainment
6.8
Comfort
7.2
Overall
7.1
Boarding
7.5
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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.
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Complete your trip to Santiago de los Caballeros by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Santiago de los Caballeros by cabin class
Find flights from Chicago to Santiago de los Caballeros, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Santiago de los Caballeros flights
Browse other Chicago and Santiago de los Caballeros flight options. Last updated on August 30, 2026.
Other flights from Chicago
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Other flights to Santiago de los Caballeros
Explore flights to Santiago de los Caballeros departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
Top 3 airlines flying from Chicago to Santiago de los Caballeros
Discover the top 3 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 7,457,451 searches. Data last updated August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$356 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$443 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$407 | Average$695 | FlexibilityNo cancel fee | On-time71% |