$143+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
May 4 — May 111
Round-trip
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 April 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 April 4, 2026.
This Priceline deal was found by Cheapflights users on 3/31. 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.
Tue 4/145:05 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Sat 4/183:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
- STI
1 stop17h 29m
Multiple Airlines
Tue 4/143:28 pm
STI
- ORD
1 stop30h 49m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$311
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Fri 5/84:15 pm
STI
- ORD
1 stop8h 00m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$366
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/247:15 pm
ORD
- STI
1 stop17h 47m
Spirit Airlines
Mon 4/273:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$380
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Sat 5/93:17 pm
STI
- ORD
1 stop8h 58m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$395
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/107:17 am
ORD
- STI
1 stop6h 06m
Spirit Airlines
Mon 4/133:28 pm
STI
- ORD
1 stop8h 49m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:27 am
MDW
- STI
2 stops13h 55m
Delta
Fri 5/86:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 4/1![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/2. 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 5/11:24 pm
MDW
- STI
2 stops9h 58m
Delta
Sat 5/96:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 4/2![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:53 pm
MDW
- STI
2 stops11h 06m
Delta
Wed 6/106:00 am
STI
- MDW
2 stops17h 17m
Delta
Deal found 4/1![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 4/4. 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.
Fri 4/179:27 am
MDW
- STI
2 stops13h 55m
Delta
Mon 4/206:00 am
STI
- MDW
2 stops12h 58m
Delta
Deal found 4/4![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 4/4. 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.
Thu 4/231:24 pm
MDW
- STI
2 stops9h 58m
Delta
Sun 4/268:59 pm
STI
- MDW
2 stops16h 44m
Delta
Deal found 4/4![Delta logo]()
$691
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:27 am
MDW
- STI
2 stops13h 55m
Delta
Mon 6/18:59 pm
STI
- MDW
2 stops15h 57m
Delta
Deal found 4/1![Delta logo]()
$1,121
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 April 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 April 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Sat 5/93:17 pm
STI
- ORD
1 stop8h 58m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 4/2. 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.
Tue 5/266:07 am
ORD
- STI
1 stop17h 52m
Delta
Thu 6/116:00 am
STI
- ORD
2 stops11h 26m
Delta
Deal found 4/2![Delta logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:05 pm
ORD
- STI
1 stop21h 07m
Multiple Airlines
Fri 6/192:46 pm
STI
- ORD
2 stops18h 17m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 3/31. 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 5/16:04 am
ORD
- STI
1 stop12h 29m
Delta
Thu 5/78:59 pm
STI
- ORD
1 stop13h 45m
Delta
Deal found 3/31![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:27 am
MDW
- STI
2 stops13h 55m
Delta
Fri 5/86:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 4/1![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:15 am
ORD
- STI
2 stops15h 07m
Delta
Fri 5/86:00 am
STI
- ORD
2 stops13h 05m
Delta
Deal found 4/1![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/2. 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.
Sat 5/27:10 am
ORD
- STI
2 stops11h 23m
Delta
Thu 5/76:00 am
STI
- ORD
2 stops15h 14m
Delta
Deal found 4/2![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:40 am
MDW
- STI
2 stops12h 53m
Delta
Sat 5/98:59 pm
STI
- MDW
2 stops15h 57m
Delta
Deal found 4/1![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:53 pm
MDW
- STI
2 stops11h 06m
Delta
Wed 6/106:00 am
STI
- MDW
2 stops17h 17m
Delta
Deal found 4/1![Delta logo]()
$545
This Delta deal was found by Cheapflights users on 4/4. 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.
Thu 4/231:24 pm
MDW
- STI
2 stops9h 58m
Delta
Sun 4/268:59 pm
STI
- MDW
2 stops16h 44m
Delta
Deal found 4/4![Delta logo]()
$691
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:05 am
MDW
- STI
2 stops13h 54m
Delta
Mon 6/291:50 pm
STI
- MDW
2 stops27h 56m
Delta
Deal found 4/1![Delta logo]()
$2,010
This Delta deal was found by Cheapflights users on 4/4. 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.
Sat 5/235:10 pm
MDW
- STI
2 stops18h 13m
Delta
Sun 5/318:59 pm
STI
- MDW
2 stops16h 43m
Delta
Deal found 4/4![Delta logo]()
$2,726
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:05 am
MDW
- STI
2 stops18h 54m
Delta
Mon 6/291:50 pm
STI
- MDW
2 stops21h 17m
Delta
Deal found 4/1![Delta logo]()
$3,033
This Delta deal was found by Cheapflights users on 3/31. 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 6/259:54 am
MDW
- STI
2 stops15h 05m
Delta
Sat 7/186:00 am
STI
- MDW
2 stops17h 15m
Delta
Deal found 3/31![Delta logo]()
$4,807
This Delta deal was found by Cheapflights users on 3/31. 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 6/266:05 am
MDW
- STI
2 stops12h 25m
Delta
Sun 7/196:00 am
STI
- MDW
2 stops13h 18m
Delta
Deal found 3/31![Delta logo]()
$6,375
Last-minute flights from Chicago to Santiago de los CaballerosDiscover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated April 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated April 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
- STI
1 stop17h 29m
Multiple Airlines
Tue 4/143:28 pm
STI
- ORD
1 stop30h 49m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$311
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/107:17 am
ORD
- STI
1 stop6h 06m
Spirit Airlines
Mon 4/133:28 pm
STI
- ORD
1 stop8h 49m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$396
This Priceline deal was found by Cheapflights users on 3/31. 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.
Tue 4/145:05 am
ORD
- STI
1 stop8h 18m
Spirit Airlines
Sat 4/183:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 4/4. 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.
Fri 4/179:27 am
MDW
- STI
2 stops13h 55m
Delta
Mon 4/206:00 am
STI
- MDW
2 stops12h 58m
Delta
Deal found 4/4![Delta logo]()
$607
This Delta deal was found by Cheapflights users on 4/4. 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.
Sat 4/189:27 am
MDW
- STI
2 stops13h 55m
Delta
Sat 4/256:00 am
STI
- MDW
2 stops12h 58m
Delta
Deal found 4/4![Delta logo]()
$2,599
This Delta deal was found by Cheapflights users on 4/4. 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.
Thu 4/231:24 pm
MDW
- STI
2 stops9h 58m
Delta
Sun 4/268:59 pm
STI
- MDW
2 stops16h 44m
Delta
Deal found 4/4![Delta logo]()
$691
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 4/247:15 pm
ORD
- STI
1 stop17h 47m
Spirit Airlines
Mon 4/273:07 pm
STI
- ORD
1 stop10h 17m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$380
This Cheapflightsfares deal was found by Cheapflights users on 4/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Fri 5/84:15 pm
STI
- ORD
1 stop8h 00m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:27 am
MDW
- STI
2 stops13h 55m
Delta
Fri 5/86:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 4/1![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/2. 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 5/11:24 pm
MDW
- STI
2 stops9h 58m
Delta
Sat 5/96:00 am
STI
- MDW
2 stops16h 09m
Delta
Deal found 4/2![Delta logo]()
$491
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:27 am
MDW
- STI
2 stops13h 55m
Delta
Mon 6/18:59 pm
STI
- MDW
2 stops15h 57m
Delta
Deal found 4/1![Delta logo]()
$1,121
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:05 am
ORD
- STI
1 stop7h 57m
Spirit Airlines
Sat 5/93:17 pm
STI
- ORD
1 stop8h 58m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$395
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 April 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 April 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Wed 4/221:27 pm
ORD
- STI
1 stop23h 35m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 4/301:27 pm
ORD
- STI
1 stop23h 35m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 5/21:27 pm
ORD
- STI
1 stop23h 35m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 5/73:44 pm
ORD
- STI
1 stop22h 36m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 5/27:15 pm
ORD
- STI
1 stop17h 47m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Fri 5/11:45 pm
ORD
- STI
1 stop23h 17m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:15 pm
ORD
- STI
1 stop17h 47m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Mon 6/295:15 am
ORD
- STI
1 stop7h 35m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 4/302:15 pm
MDW
- STI
2 stops22h 47m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 5/26:00 am
MDW
- STI
2 stops31h 02m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$210
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- STI
2 stops12h 33m
Delta
Deal found 4/1![Delta logo]()
$211
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:50 am
ORD
- STI
2 stops14h 47m
Delta
Deal found 4/1![Delta logo]()
$211
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 April 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Priceline) |
One-way from | $143 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $506 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Santiago de los Caballeros that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 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
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sat 5/2
5:05 am-2:02 pm
1 stop7h 57m
Santiago de los Caballeros
Sat 5/9
3:17 pm-11:15 pm
1 stop8h 58m
$406
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Tue 5/26
6:07 am-12:59 am
1 stop17h 52m
Santiago de los Caballeros
Thu 6/11
6:00 am-4:26 pm
2 stops11h 26m
$460
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 5/1
6:04 am-7:33 pm
1 stop12h 29m
Santiago de los Caballeros
Thu 5/7
8:59 pm-9:44 am
1 stop13h 45m
$466
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 5/15
4:05 pm-2:12 pm
1 stop21h 07m
Santiago de los Caballeros
Fri 6/19
2:46 pm-8:03 am
2 stops18h 17m
$470
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Fri 5/1
9:27 am-12:22 am
2 stops13h 55m
Santiago de los Caballeros
Fri 5/8
6:00 am-9:09 pm
2 stops16h 09m
$471
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 5/1
8:15 am-12:22 am
2 stops15h 07m
Santiago de los Caballeros
Fri 5/8
6:00 am-6:05 pm
2 stops13h 05m
$471
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sat 5/2
7:10 am-7:33 pm
2 stops11h 23m
Santiago de los Caballeros
Thu 5/7
6:00 am-8:14 pm
2 stops15h 14m
$471
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Sat 5/2
5:40 am-7:33 pm
2 stops12h 53m
Santiago de los Caballeros
Sat 5/9
8:59 pm-11:56 am
2 stops15h 57m
$491
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Mon 6/1
12:53 pm-12:59 am
2 stops11h 06m
Santiago de los Caballeros
Wed 6/10
6:00 am-10:17 pm
2 stops17h 17m
$545
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Thu 4/23
1:24 pm-12:22 am
2 stops9h 58m
Santiago de los Caballeros
Sun 4/26
8:59 pm-12:43 pm
2 stops16h 44m
$691
Showing 1-10 of 30 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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 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 $431). 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 April 4, 2026.
Peruse reviews from past customers who have flown with American Airlines and Spirit 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.
Food
6.4
Entertainment
6.9
Crew
7.9
Comfort
7.2
Boarding
7.5
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Food
6.4
Entertainment
6.9
Crew
7.9
Comfort
7.2
Boarding
7.5
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Food
6.4
Entertainment
6.9
Crew
7.9
Comfort
7.2
Boarding
7.5
Overall
7.1
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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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 April 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 April 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 April 4, 2026.
Top 4 airlines flying from Chicago to Santiago de los Caballeros
Discover the top 4 airlines that operate flights from Chicago to Santiago de los Caballeros. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$255 | Average$443 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$298 | Average$441 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$356 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$437 | Average$745 | FlexibilityNo cancel fee | On-time71% |