$164+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — STI
Jun 23 — Jun 301
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 May 24, 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 May 24, 2026.
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:05 am
ORD
- STI
1 stop14h 54m
Delta
Sun 6/148:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/20![Delta logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:29 pm
ORD
- STI
1 stop14h 43m
American Airlines
Sun 6/141:14 pm
STI
- ORD
1 stop12h 20m
American Airlines
Deal found 5/22![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/23. 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 8/175:59 pm
ORD
- STI
1 stop19h 36m
American Airlines
Fri 8/217:00 am
STI
- ORD
1 stop9h 05m
American Airlines
Deal found 5/23![American Airlines logo]()
$361
This JetBlue deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- STI
1 stop6h 36m
JetBlue
Wed 9/25:01 am
STI
- ORD
1 stop9h 38m
JetBlue
Deal found 5/20![JetBlue logo]()
$384
This American Airlines deal was found by Cheapflights users on 5/22. 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 8/287:09 am
ORD
- STI
1 stop12h 54m
American Airlines
Sun 9/61:32 pm
STI
- ORD
1 stop11h 12m
American Airlines
Deal found 5/22![American Airlines logo]()
$407
This Cheapflightsfares deal was found by Cheapflights users on 5/24. 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 10/282:35 pm
ORD
- STI
1 stop8h 16m
JetBlue
Tue 11/106:01 am
STI
- ORD
1 stop9h 38m
JetBlue
Deal found 5/24![JetBlue logo]()
$411
This American Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:08 am
ORD
- STI
1 stop14h 05m
American Airlines
Sun 6/141:14 pm
STI
- ORD
1 stop12h 20m
American Airlines
Deal found 5/23![American Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop12h 06m
Delta
Tue 11/106:40 am
STI
- ORD
2 stops15h 44m
Delta
Deal found 5/20![Delta logo]()
$421
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:45 pm
ORD
- STI
1 stop14h 37m
American Airlines
Thu 11/127:00 am
STI
- ORD
1 stop19h 21m
American Airlines
Deal found 5/19![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 5/23. 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 6/116:00 am
MDW
- STI
2 stops18h 59m
Delta
Sun 6/288:59 pm
STI
- MDW
2 stops19h 41m
Delta
Deal found 5/23![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 5/23. 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 6/911:05 am
MDW
- STI
2 stops13h 54m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/23![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 5/22. 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 6/69:23 am
MDW
- STI
2 stops14h 36m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/22![Delta logo]()
$762
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 May 24, 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 May 24, 2026.
This JetBlue deal was found by Cheapflights users on 5/23. 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 9/17:00 am
ORD
- STI
1 stop6h 36m
JetBlue
Wed 9/25:01 am
STI
- ORD
1 stop9h 38m
JetBlue
Deal found 5/23![JetBlue logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/23. 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 8/175:59 pm
ORD
- STI
1 stop19h 36m
American Airlines
Fri 8/217:00 am
STI
- ORD
1 stop9h 05m
American Airlines
Deal found 5/23![American Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 5/24. 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 stop12h 06m
Delta
Tue 11/106:40 am
STI
- ORD
2 stops15h 44m
Delta
Deal found 5/24![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 5/22. 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 6/610:15 am
ORD
- STI
2 stops13h 44m
Delta
Sun 6/148:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/22![Delta logo]()
$421
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:59 am
ORD
- STI
1 stop13h 30m
American Airlines
Sun 8/97:00 am
STI
- ORD
1 stop17h 00m
American Airlines
Deal found 5/20![American Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:59 pm
ORD
- STI
1 stop11h 00m
Delta
Tue 6/98:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/21![Delta logo]()
$475
This Frontier deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2412:04 pm
MDW
- STI
2 stops20h 50m
Frontier
Sun 6/2811:09 am
STI
- MDW
2 stops12h 02m
Frontier
Deal found 5/21![Frontier logo]()
$1,142
This Delta deal was found by Cheapflights users on 5/23. 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 6/1210:05 am
ORD
- STI
1 stop14h 54m
Delta
Tue 6/236:00 am
STI
- ORD
1 stop16h 48m
Delta
Deal found 5/23![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 5/23. 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 8/178:48 am
ORD
- STI
2 stops16h 07m
Delta
Fri 8/218:59 pm
STI
- ORD
2 stops18h 49m
Delta
Deal found 5/23![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 5/23. 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 6/116:00 am
MDW
- STI
2 stops18h 59m
Delta
Sun 6/288:59 pm
STI
- MDW
2 stops19h 41m
Delta
Deal found 5/23![Delta logo]()
$672
This Delta deal was found by Cheapflights users on 5/23. 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 6/911:05 am
MDW
- STI
2 stops13h 54m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/23![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 5/22. 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 6/69:23 am
MDW
- STI
2 stops14h 36m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/22![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 5/23. 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 6/1111:05 am
MDW
- STI
2 stops13h 54m
Delta
Sat 6/278:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/23![Delta logo]()
$1,765
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:54 am
MDW
- STI
2 stops15h 05m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops14h 10m
Delta
Deal found 5/20![Delta logo]()
$1,801
This Delta deal was found by Cheapflights users on 5/22. 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 6/1212:50 pm
MDW
- STI
2 stops12h 09m
Delta
Mon 6/226:00 am
STI
- MDW
2 stops17h 17m
Delta
Deal found 5/22![Delta logo]()
$2,416
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:22 am
MDW
- STI
2 stops14h 37m
Delta
Tue 6/98:59 pm
STI
- MDW
2 stops14h 10m
Delta
Deal found 5/21![Delta logo]()
$2,615
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:22 pm
MDW
- STI
2 stops10h 37m
Delta
Mon 6/88:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/21![Delta logo]()
$2,721
Last-minute flights from Chicago to Santiago de los CaballerosDiscover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated May 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santiago de los Caballeros. Data last updated May 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:59 pm
ORD
- STI
1 stop11h 00m
Delta
Thu 6/118:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/20![Delta logo]()
$475
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:13 pm
ORD
- STI
1 stop18h 08m
American Airlines
Fri 6/57:04 am
STI
- ORD
1 stop17h 26m
American Airlines
Deal found 5/22![American Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 5/22. 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 5/305:41 pm
ORD
- STI
2 stops17h 42m
Delta
Fri 6/58:59 pm
STI
- ORD
1 stop16h 17m
Delta
Deal found 5/22![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:08 am
ORD
- STI
1 stop14h 05m
American Airlines
Sun 6/141:14 pm
STI
- ORD
1 stop12h 20m
American Airlines
Deal found 5/23![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:29 pm
ORD
- STI
1 stop14h 43m
American Airlines
Sun 6/141:14 pm
STI
- ORD
1 stop12h 20m
American Airlines
Deal found 5/22![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/22. 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 6/610:15 am
ORD
- STI
2 stops13h 44m
Delta
Sun 6/148:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/22![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 5/22. 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 6/69:23 am
MDW
- STI
2 stops14h 36m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/22![Delta logo]()
$762
This Delta deal was found by Cheapflights users on 5/22. 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 6/911:23 am
ORD
- STI
2 stops13h 36m
Delta
Fri 6/128:59 pm
STI
- ORD
2 stops18h 15m
Delta
Deal found 5/22![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 5/23. 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 6/911:05 am
MDW
- STI
2 stops13h 54m
Delta
Sun 6/148:59 pm
STI
- MDW
2 stops16h 47m
Delta
Deal found 5/23![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:05 am
ORD
- STI
1 stop14h 54m
Delta
Sun 6/148:59 pm
STI
- ORD
1 stop13h 26m
Delta
Deal found 5/20![Delta logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:00 am
ORD
- STI
2 stops12h 12m
American Airlines
Sun 6/141:14 pm
STI
- ORD
1 stop12h 20m
American Airlines
Deal found 5/20![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 5/23. 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 6/116:00 am
MDW
- STI
2 stops18h 59m
Delta
Sun 6/288:59 pm
STI
- MDW
2 stops19h 41m
Delta
Deal found 5/23![Delta logo]()
$672
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 May 24, 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 May 24, 2026.
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:26 pm
ORD
- STI
1 stop13h 46m
American Airlines
Deal found 5/19![American Airlines logo]()
$164
This Super.com deal was found by Cheapflights users on 5/22. 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.
Sun 10/257:00 am
ORD
- STI
1 stop6h 34m
JetBlue
Deal found 5/22![JetBlue logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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 5/23![JetBlue logo]()
$191
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:53 pm
MDW
- STI
2 stops11h 06m
Delta
Deal found 5/19![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:15 am
ORD
- STI
1 stop13h 44m
Delta
Deal found 5/19![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 5/23. 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 6/312:53 pm
MDW
- STI
2 stops11h 06m
Delta
Deal found 5/23![Delta logo]()
$226
This American Airlines deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:45 pm
ORD
- STI
1 stop14h 36m
American Airlines
Deal found 5/23![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 5/22. 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 5/299:19 pm
ORD
- STI
1 stop14h 02m
American Airlines
Deal found 5/22![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:05 am
ORD
- STI
2 stops11h 01m
Delta
Deal found 5/21![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:42 am
ORD
- STI
2 stops15h 17m
Delta
Deal found 5/19![Delta logo]()
$287
This American Airlines deal was found by Cheapflights users on 5/22. 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 6/226:59 am
ORD
- STI
1 stop13h 13m
American Airlines
Deal found 5/22![American Airlines logo]()
$305
This Justfly.com deal was found by Cheapflights users on 5/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/128:20 pm
ORD
- STI
1 stop28h 25m
JetBlue
Deal found 5/22![JetBlue logo]()
$310
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 May 24, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $352 (Delta) |
One-way from | $164 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $544 |
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 May 24, 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
Tue 9/1
7:00 am-2:36 pm
1 stop6h 36m
Santiago de los Caballeros
Wed 9/2
5:01 am-1:39 pm
1 stop9h 38m
$352
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 8/17
5:59 pm-2:35 pm
1 stop19h 36m
Santiago de los Caballeros
Fri 8/21
7:00 am-3:05 pm
1 stop9h 05m
$361
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Wed 10/28
6:00 am-7:06 pm
1 stop12h 06m
Santiago de los Caballeros
Tue 11/10
6:40 am-8:24 pm
2 stops15h 44m
$421
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sat 6/6
10:15 am-12:59 am
2 stops13h 44m
Santiago de los Caballeros
Sun 6/14
8:59 pm-9:25 am
1 stop13h 26m
$421
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 6/5
12:59 pm-12:59 am
1 stop11h 00m
Santiago de los Caballeros
Tue 6/9
8:59 pm-9:25 am
1 stop13h 26m
$475
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Sun 8/2
6:59 am-9:29 pm
1 stop13h 30m
Santiago de los Caballeros
Sun 8/9
7:00 am-11:00 pm
1 stop17h 00m
$514
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Fri 6/12
10:05 am-1:59 am
1 stop14h 54m
Santiago de los Caballeros
Tue 6/23
6:00 am-9:48 pm
1 stop16h 48m
$571
ChicagoSantiago de los Caballeros
ORD - STI
ORDSTI
Chicago O'Hare Intl
Mon 8/17
8:48 am-1:55 am
2 stops16h 07m
Santiago de los Caballeros
Fri 8/21
8:59 pm-2:48 pm
2 stops18h 49m
$588
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Thu 6/11
6:00 am-1:59 am
2 stops18h 59m
Santiago de los Caballeros
Sun 6/28
8:59 pm-3:40 pm
2 stops19h 41m
$672
ChicagoSantiago de los Caballeros
MDW - STI
MDWSTI
Chicago Midway
Tue 6/9
11:05 am-1:59 am
2 stops13h 54m
Santiago de los Caballeros
Sun 6/14
8:59 pm-12:46 pm
2 stops16h 47m
$698
Showing 1-10 of 29 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 May.
| 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
MDW-STI
ORD-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
MDW-STI
ORD-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.
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 May 24, 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.
Overall
7.1
Comfort
7.2
Boarding
7.5
Crew
7.9
Entertainment
6.9
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Overall
7.1
Comfort
7.2
Boarding
7.5
Crew
7.9
Entertainment
6.9
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Spirit Airlines
Overall
7.1
Comfort
7.2
Boarding
7.5
Crew
7.9
Entertainment
6.9
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Santiago de los Caballeros. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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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 May 24, 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 May 24, 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 May 24, 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 May 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$287 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$298 | Average$441 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$445 | Average$741 | FlexibilityNo cancel fee | On-time71% |