$170+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Aug 9 — Aug 161
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 July 10, 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 July 10, 2026.
This SmartFares deal was found by Cheapflights users on 7/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Fri 8/284:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/7![JetBlue logo]()
$345
This SmartFares deal was found by Cheapflights users on 7/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Thu 8/274:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/6![JetBlue logo]()
$347
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 8/247:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Thu 8/274:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/6![JetBlue logo]()
$370
This Cheapflightsfares deal was found by Cheapflights users on 7/9. 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 9/216:00 am
ORD
- STI
1 stop6h 27m
JetBlue
Thu 9/243:49 pm
STI
- ORD
1 stop8h 42m
JetBlue
Deal found 7/9![JetBlue logo]()
$375
This American Airlines deal was found by Cheapflights users on 7/10. 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 9/219:01 pm
ORD
- STI
2 stops16h 14m
American Airlines
Thu 9/243:15 pm
STI
- ORD
2 stops18h 37m
American Airlines
Deal found 7/10![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am
ORD
- STI
1 stop7h 12m
American Airlines
Tue 11/104:36 pm
STI
- ORD
1 stop17h 06m
American Airlines
Deal found 7/6![American Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/247:11 pm
ORD
- STI
1 stop16h 11m
American Airlines
Thu 8/277:00 am
STI
- ORD
1 stop17h 30m
American Airlines
Deal found 7/10![American Airlines logo]()
$428
This SmartFares deal was found by Cheapflights users on 7/9. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am
ORD
- STI
1 stop6h 45m
JetBlue
Mon 10/265:01 am
STI
- ORD
1 stop9h 38m
JetBlue
Deal found 7/9![JetBlue logo]()
$431
This Delta deal was found by Cheapflights users on 7/6. 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 8/246:05 am
MDW
- STI
2 stops12h 29m
Delta
Mon 9/147:30 pm
STI
- MDW
2 stops21h 46m
Delta
Deal found 7/6![Delta logo]()
$562
This Delta deal was found by Cheapflights users on 7/5. 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 10/175:21 pm
MDW
- STI
2 stops17h 42m
Delta
Mon 10/267:16 pm
STI
- MDW
2 stops23h 49m
Delta
Deal found 7/5![Delta logo]()
$964
This Delta deal was found by Cheapflights users on 7/10. 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 8/224:39 pm
MDW
- STI
2 stops18h 51m
Delta
Sat 8/296:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/10![Delta logo]()
$1,568
This Delta deal was found by Cheapflights users on 7/6. 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 8/199:24 am
MDW
- STI
2 stops15h 31m
Delta
Wed 8/266:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/6![Delta logo]()
$1,769
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 July 10, 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 July 10, 2026.
This JetBlue deal was found by Cheapflights users on 7/9. 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 9/206:00 am
ORD
- STI
1 stop6h 27m
JetBlue
Thu 9/243:49 pm
STI
- ORD
1 stop8h 42m
JetBlue
Deal found 7/9![JetBlue logo]()
$378
This American Airlines deal was found by Cheapflights users on 7/10. 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 9/217:00 pm
ORD
- STI
1 stop18h 15m
American Airlines
Thu 9/243:15 pm
STI
- ORD
1 stop17h 33m
American Airlines
Deal found 7/10![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 7/7. 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 10/286:00 am
ORD
- STI
1 stop10h 46m
Delta
Tue 11/109:00 pm
STI
- ORD
1 stop15h 04m
Delta
Deal found 7/7![Delta logo]()
$440
This JetBlue deal was found by Cheapflights users on 7/7. 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.
Fri 8/217:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Fri 8/284:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/7![JetBlue logo]()
$378
This Delta deal was found by Cheapflights users on 7/7. 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 9/216:25 pm
ORD
- STI
2 stops17h 01m
Delta
Thu 9/247:30 pm
STI
- ORD
2 stops22h 00m
Delta
Deal found 7/7![Delta logo]()
$502
This JetBlue deal was found by Cheapflights users on 7/10. 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.
Sat 8/227:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Sat 8/294:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/10![JetBlue logo]()
$476
This JetBlue deal was found by Cheapflights users on 7/9. 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 8/237:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Sun 8/304:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/9![JetBlue logo]()
$476
This Delta deal was found by Cheapflights users on 7/6. 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 8/245:30 am
ORD
- STI
2 stops13h 04m
Delta
Mon 9/147:30 pm
STI
- ORD
2 stops19h 59m
Delta
Deal found 7/6![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 7/6. 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 8/246:05 am
MDW
- STI
2 stops12h 29m
Delta
Mon 9/147:30 pm
STI
- MDW
2 stops21h 46m
Delta
Deal found 7/6![Delta logo]()
$562
This Cheapflightsfares deal was found by Cheapflights users on 7/5. 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 8/12:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Thu 8/64:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/5![JetBlue logo]()
$512
This Cheapflightsfares deal was found by Cheapflights users on 7/5. 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 7/312:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Thu 8/64:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/5![JetBlue logo]()
$546
This Delta deal was found by Cheapflights users on 7/5. 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 10/175:21 pm
MDW
- STI
2 stops17h 42m
Delta
Mon 10/267:16 pm
STI
- MDW
2 stops23h 49m
Delta
Deal found 7/5![Delta logo]()
$964
This Delta deal was found by Cheapflights users on 7/10. 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 8/224:39 pm
MDW
- STI
2 stops18h 51m
Delta
Sat 8/296:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/10![Delta logo]()
$1,568
This Delta deal was found by Cheapflights users on 7/6. 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 8/199:24 am
MDW
- STI
2 stops15h 31m
Delta
Wed 8/266:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/6![Delta logo]()
$1,769
This Delta deal was found by Cheapflights users on 7/8. 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 8/261:25 pm
MDW
- STI
2 stops11h 30m
Delta
Tue 9/87:30 pm
STI
- MDW
2 stops18h 50m
Delta
Deal found 7/8![Delta logo]()
$2,078
This Delta deal was found by Cheapflights users on 7/5. 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 7/316:00 am
MDW
- STI
2 stops12h 34m
Delta
Thu 8/68:59 pm
STI
- MDW
2 stops15h 52m
Delta
Deal found 7/5![Delta logo]()
$3,648
Last-minute flights from Chicago to Santiago de los CaballerosDiscover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated July 10, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 8/12:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Tue 8/45:01 am
STI
- ORD
1 stop9h 38m
JetBlue
Deal found 7/6![JetBlue logo]()
$439
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 8/12:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Thu 8/64:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/6![JetBlue logo]()
$472
This Delta deal was found by Cheapflights users on 7/6. 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 8/199:24 am
MDW
- STI
2 stops15h 31m
Delta
Wed 8/266:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/6![Delta logo]()
$1,769
This SmartFares deal was found by Cheapflights users on 7/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Thu 8/274:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/6![JetBlue logo]()
$347
This SmartFares deal was found by Cheapflights users on 7/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Fri 8/284:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/7![JetBlue logo]()
$345
This Cheapflightsfares deal was found by Cheapflights users on 7/10. 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 8/227:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Fri 8/284:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/10![JetBlue logo]()
$443
This SmartFares deal was found by Cheapflights users on 7/5. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Mon 8/314:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/5![JetBlue logo]()
$460
This Delta deal was found by Cheapflights users on 7/10. 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 8/224:39 pm
MDW
- STI
2 stops18h 51m
Delta
Sat 8/296:00 am
STI
- MDW
2 stops17h 36m
Delta
Deal found 7/10![Delta logo]()
$1,568
This SmartFares deal was found by Cheapflights users on 7/9. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Sun 8/304:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/9![JetBlue logo]()
$468
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 8/247:00 am
ORD
- STI
1 stop7h 01m
JetBlue
Thu 8/274:54 pm
STI
- ORD
1 stop7h 50m
JetBlue
Deal found 7/6![JetBlue logo]()
$370
This American Airlines deal was found by Cheapflights users on 7/10. 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 8/247:11 pm
ORD
- STI
1 stop16h 11m
American Airlines
Thu 8/277:00 am
STI
- ORD
1 stop17h 30m
American Airlines
Deal found 7/10![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 7/6. 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 8/246:05 am
MDW
- STI
2 stops12h 29m
Delta
Mon 9/147:30 pm
STI
- MDW
2 stops21h 46m
Delta
Deal found 7/6![Delta logo]()
$562
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 July 10, 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 July 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 8/12:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Deal found 7/6![JetBlue logo]()
$170
This JetBlue deal was found by Cheapflights users on 7/7. 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 10/46:00 am
ORD
- STI
1 stop6h 27m
JetBlue
Deal found 7/7![JetBlue logo]()
$172
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am
ORD
- STI
1 stop7h 12m
American Airlines
Deal found 7/10![American Airlines logo]()
$175
This American Airlines deal was found by Cheapflights users on 7/6. 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 8/288:54 am
ORD
- STI
2 stops11h 13m
American Airlines
Deal found 7/6![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 7/6. 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 10/287:10 am
ORD
- STI
2 stops9h 36m
Delta
Deal found 7/6![Delta logo]()
$203
This Cheapflightsfares deal was found by Cheapflights users on 7/9. 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 10/287:00 am
ORD
- STI
1 stop6h 34m
JetBlue
Deal found 7/9![JetBlue logo]()
$204
This Delta deal was found by Cheapflights users on 7/7. 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 10/25:11 pm
MDW
- STI
2 stops18h 15m
Delta
Deal found 7/7![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 7/7. 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 10/37:00 am
ORD
- STI
1 stop9h 59m
Delta
Deal found 7/7![Delta logo]()
$222
This Frontier deal was found by Cheapflights users on 7/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:52 pm
ORD
- STI
1 stop12h 07m
Frontier
Deal found 7/8![Frontier logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 7/292:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Deal found 7/8![JetBlue logo]()
$234
This JetBlue deal was found by Cheapflights users on 7/8. 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 7/282:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Deal found 7/8![JetBlue logo]()
$236
This Super.com deal was found by Cheapflights users on 7/7. 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.
Sat 7/258:52 pm
ORD
- STI
1 stop12h 07m
Frontier
Deal found 7/7![Frontier logo]()
$241
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 July 10, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $345 (SmartFares) |
One-way from | $170 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $484 |
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 July 10, 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 - STI
ORDSTI
Chicago O'Hare Intl
Sun 9/20
6:00 am-1:27 pm
1 stop6h 27m
Santiago de los Caballeros
Thu 9/24
3:49 pm-11:31 pm
1 stop8h 42m
$378
Quickest round-trip
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 8/21
7:00 am-3:01 pm
1 stop7h 01m
Santiago de los Caballeros
Fri 8/28
4:54 pm-11:44 pm
1 stop7h 50m
$378
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 9/21
7:00 pm-2:15 pm
1 stop18h 15m
Santiago de los Caballeros
Thu 9/24
3:15 pm-7:48 am
1 stop17h 33m
$393
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Wed 10/28
6:00 am-5:46 pm
1 stop10h 46m
Santiago de los Caballeros
Tue 11/10
9:00 pm-10:04 am
1 stop15h 04m
$440
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sat 8/22
7:00 am-3:01 pm
1 stop7h 01m
Santiago de los Caballeros
Sat 8/29
4:54 pm-11:44 pm
1 stop7h 50m
$476
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 8/23
7:00 am-3:01 pm
1 stop7h 01m
Santiago de los Caballeros
Sun 8/30
4:54 pm-11:44 pm
1 stop7h 50m
$476
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 9/21
6:25 pm-12:26 pm
2 stops17h 01m
Santiago de los Caballeros
Thu 9/24
7:30 pm-4:30 pm
2 stops22h 00m
$502
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sat 8/1
2:35 pm-11:51 pm
1 stop8h 16m
Santiago de los Caballeros
Thu 8/6
4:54 pm-11:44 pm
1 stop7h 50m
$512
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 7/31
2:35 pm-11:51 pm
1 stop8h 16m
Santiago de los Caballeros
Thu 8/6
4:54 pm-11:44 pm
1 stop7h 50m
$546
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 8/24
5:30 am-7:34 pm
2 stops13h 04m
Santiago de los Caballeros
Mon 9/14
7:30 pm-2:29 pm
2 stops19h 59m
$556
Showing 1-10 of 34 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 July.
| 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 Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Santiago de los Caballeros flight deals on Cheapflights vs. Ovago >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 Ovago the most. Ovago 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 September is currently the most expensive (average of $422). 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 July 10, 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.
Boarding
7.5
Entertainment
6.8
Crew
7.9
Overall
7.1
Comfort
7.2
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.5
Entertainment
6.8
Crew
7.9
Overall
7.1
Comfort
7.2
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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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
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Chicago and Santiago de los Caballeros flights
Browse other Chicago and Santiago de los Caballeros flight options. Last updated on July 10, 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 July 10, 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 July 10, 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 2,558,603 searches. Data last updated July 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$443 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$407 | Average$741 | FlexibilityNo cancel fee | On-time71% |