$140+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Chicago to Santiago de los Caballeros with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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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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 February 4, 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 February 4, 2026.
This Expedia deal was found by Cheapflights users on 2/2. 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 3/97:00 am
ORD
- STI
1 stop6h 33m
Spirit Airlines
Thu 3/123:43 pm
STI
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Sat 3/78:16 pm
ORD
- STI
1 stop16h 17m
Spirit Airlines
Sun 3/152:46 am
STI
- ORD
1 stop15h 29m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$266
This Priceline deal was found by Cheapflights users on 2/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:05 am
ORD
- STI
1 stop6h 30m
Spirit Airlines
Sat 4/253:40 pm
STI
- ORD
1 stop9h 01m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 4/201:27 pm
ORD
- STI
1 stop24h 08m
Multiple Airlines
Mon 4/273:40 pm
STI
- ORD
1 stop30h 37m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$299
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Sun 4/195:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Fri 4/243:40 pm
STI
- ORD
1 stop9h 01m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$304
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Mon 3/166:10 pm
ORD
- STI
1 stop6h 39m
Spirit Airlines
Wed 3/182:46 am
STI
- ORD
1 stop9h 31m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/117:20 am
ORD
- STI
1 stop6h 13m
Spirit Airlines
Wed 2/254:40 pm
STI
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/105:15 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Tue 2/244:40 pm
STI
- ORD
1 stop20h 42m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/105:15 am
ORD
- STI
1 stop8h 18m
Multiple Airlines
Fri 2/204:40 pm
STI
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 2/2. 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 2/26:35 pm
MDW
- STI
2 stops23h 59m
Delta
Mon 2/99:59 pm
STI
- MDW
2 stops16h 00m
Delta
Deal found 2/2![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:35 am
MDW
- STI
2 stops13h 19m
Delta
Mon 3/308:40 pm
STI
- MDW
2 stops16h 49m
Delta
Deal found 2/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 2/2. 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 2/89:33 am
MDW
- STI
2 stops13h 17m
Delta
Sun 2/159:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$980
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 February 4, 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 February 4, 2026.
This Expedia deal was found by Cheapflights users on 2/2. 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 3/97:00 am
ORD
- STI
1 stop6h 33m
Spirit Airlines
Thu 3/123:43 pm
STI
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 4/201:27 pm
ORD
- STI
1 stop24h 08m
Multiple Airlines
Mon 4/273:40 pm
STI
- ORD
1 stop30h 37m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$299
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Sun 4/195:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Fri 4/243:40 pm
STI
- ORD
1 stop9h 01m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/106:36 pm
ORD
- STI
1 stop18h 57m
Multiple Airlines
Sun 3/153:43 pm
STI
- ORD
1 stop26h 32m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$309
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Mon 3/166:10 pm
ORD
- STI
1 stop6h 39m
Spirit Airlines
Wed 3/182:46 am
STI
- ORD
1 stop9h 31m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/117:20 am
ORD
- STI
1 stop6h 13m
Spirit Airlines
Wed 2/254:40 pm
STI
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/155:15 am
ORD
- STI
1 stop8h 20m
Multiple Airlines
Thu 2/194:40 pm
STI
- ORD
1 stop8h 44m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$341
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 4/205:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Sat 4/253:40 pm
STI
- ORD
1 stop9h 01m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/2. 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 2/89:33 am
MDW
- STI
2 stops13h 17m
Delta
Sun 2/159:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$980
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/155:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Thu 2/194:40 pm
STI
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/155:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Fri 2/204:40 pm
STI
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 2/2. 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 2/169:34 am
MDW
- STI
2 stops14h 00m
Delta
Mon 3/29:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$1,119
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
MDW
- STI
2 stops12h 15m
Delta
Sun 3/158:40 pm
STI
- MDW
2 stops16h 49m
Delta
Deal found 2/4![Delta logo]()
$1,654
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:35 am
MDW
- STI
2 stops13h 19m
Delta
Wed 3/256:33 am
STI
- MDW
2 stops12h 21m
Delta
Deal found 2/4![Delta logo]()
$1,734
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/299:35 am
MDW
- STI
2 stops13h 30m
Delta
Fri 4/36:00 am
STI
- MDW
2 stops12h 54m
Delta
Deal found 2/3![Delta logo]()
$1,988
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1210:49 am
MDW
- STI
2 stops12h 45m
Delta
Sun 2/159:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/3![Delta logo]()
$2,016
This Delta deal was found by Cheapflights users on 2/2. 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 3/2710:45 am
MDW
- STI
2 stops12h 09m
Delta
Sun 3/298:40 pm
STI
- MDW
2 stops16h 49m
Delta
Deal found 2/2![Delta logo]()
$6,014
Last-minute flights from Chicago to Santiago de los CaballerosDiscover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated February 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/2. 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 2/61:26 pm
MDW
- STI
2 stops9h 24m
Delta
Mon 2/96:39 am
STI
- MDW
2 stops13h 57m
Delta
Deal found 2/2![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 2/2. 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 2/89:33 am
MDW
- STI
2 stops13h 17m
Delta
Sun 2/159:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$980
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/105:15 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Tue 2/244:40 pm
STI
- ORD
1 stop20h 42m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/105:15 am
ORD
- STI
1 stop8h 18m
Multiple Airlines
Fri 2/204:40 pm
STI
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 2/105:15 am
ORD
- STI
1 stop8h 18m
Multiple Airlines
Thu 2/194:40 pm
STI
- ORD
1 stop8h 44m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$328
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 2/117:20 am
ORD
- STI
1 stop6h 13m
Spirit Airlines
Wed 2/254:40 pm
STI
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sun 2/155:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Tue 2/244:40 pm
STI
- ORD
1 stop20h 42m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 2/2. 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 2/169:34 am
MDW
- STI
2 stops14h 00m
Delta
Mon 3/29:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 2/2![Delta logo]()
$1,119
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Sat 3/78:16 pm
ORD
- STI
1 stop16h 17m
Spirit Airlines
Sun 3/152:46 am
STI
- ORD
1 stop15h 29m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$266
This Expedia deal was found by Cheapflights users on 2/2. 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 3/97:00 am
ORD
- STI
1 stop6h 33m
Spirit Airlines
Thu 3/123:43 pm
STI
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Mon 3/166:10 pm
ORD
- STI
1 stop6h 39m
Spirit Airlines
Wed 3/182:46 am
STI
- ORD
1 stop9h 31m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 2/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:35 am
MDW
- STI
2 stops13h 19m
Delta
Mon 3/308:40 pm
STI
- MDW
2 stops16h 49m
Delta
Deal found 2/4![Delta logo]()
$561
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 February 4, 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 February 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Sun 4/55:05 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$140
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:15 am
ORD
- STI
1 stop8h 20m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 4/24:36 pm
ORD
- STI
1 stop8h 13m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 2/267:00 am
ORD
- STI
2 stops30h 35m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 3/289:16 pm
MDW
- STI
2 stops16h 07m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 4/24:00 pm
ORD
- STI
2 stops21h 23m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 3/284:51 pm
ORD
- STI
2 stops20h 32m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:55 am
ORD
- STI
2 stops13h 59m
Delta
Deal found 2/3![Delta logo]()
$363
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $250 (Expedia) |
One-way from | $140 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $557 |
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 February 4, 2026.
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 3/9
7:00 am-2:33 pm
1 stop6h 33m
Santiago de los Caballeros
Thu 3/12
3:43 pm-11:17 pm
1 stop8h 34m
$250
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 4/20
1:27 pm-2:35 pm
1 stop24h 08m
Santiago de los Caballeros
Mon 4/27
3:40 pm-9:17 pm
1 stop30h 37m
$299
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 4/19
5:15 am-2:35 pm
1 stop8h 20m
Santiago de los Caballeros
Fri 4/24
3:40 pm-11:41 pm
1 stop9h 01m
$304
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 3/16
6:10 pm-1:49 am
1 stop6h 39m
Santiago de los Caballeros
Wed 3/18
2:46 am-11:17 am
1 stop9h 31m
$308
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Tue 3/10
6:36 pm-2:33 pm
1 stop18h 57m
Santiago de los Caballeros
Sun 3/15
3:43 pm-5:15 pm
1 stop26h 32m
$309
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Wed 2/11
7:20 am-3:33 pm
1 stop6h 13m
Santiago de los Caballeros
Wed 2/25
4:40 pm-11:47 pm
1 stop9h 07m
$309
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 4/20
5:15 am-2:35 pm
1 stop8h 20m
Santiago de los Caballeros
Sat 4/25
3:40 pm-11:41 pm
1 stop9h 01m
$324
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 2/15
5:15 am-3:35 pm
1 stop8h 20m
Santiago de los Caballeros
Thu 2/19
4:40 pm-11:47 pm
1 stop9h 07m
$340
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 2/15
5:15 am-3:35 pm
1 stop8h 20m
Santiago de los Caballeros
Thu 2/19
4:40 pm-11:24 pm
1 stop8h 44m
$341
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 2/15
5:15 am-3:35 pm
1 stop8h 20m
Santiago de los Caballeros
Fri 2/20
4:40 pm-11:47 pm
1 stop9h 07m
$341
Showing 1-10 of 25 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 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, November is the cheapest month in which you can book a flight from Chicago to Santiago de los Caballeros (average of $206). Flying from Chicago 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.
How much does it cost to fly round-trip from Chicago to Santiago de los Caballeros?
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 February 4, 2026.
Peruse reviews from past customers who have flown with United Airlines and 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.
Comfort
7.3
Food
6.6
Crew
8.1
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Crew
8.1
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Comfort
7.3
Food
6.6
Crew
8.1
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
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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Alternative routes for Chicago to Santiago de los Caballeros
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Complete your trip
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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 February 4, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 4, 2026.
Top 5 airlines flying from Chicago to Santiago de los Caballeros
Discover the top 5 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$226 | Average$677 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$255 | Average$471 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$298 | Average$441 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$356 | Average$422 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$437 | Average$772 | FlexibilityNo cancel fee | On-time71% |