$162+ Cheap flights from Chicago (CHI) to Santo Domingo (SDQ)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDQ
Jul 12 — Jul 191
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Santo Domingo 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
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Cheapest flights from Chicago to Santo DomingoExplore the most affordable flight options available from Chicago to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2026.
Explore the most affordable flight options available from Chicago to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2026.
This Faresmojo deal was found by Cheapflights users on 6/9. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Tue 9/14:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/9![JetBlue logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/2812:29 am
ORD
- SDQ
1 stop17h 49m
Multiple Airlines
Sat 9/53:30 pm
SDQ
- ORD
1 stop7h 56m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$330
This Super.com deal was found by Cheapflights users on 6/7. 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.
Sun 9/136:00 am
ORD
- SDQ
1 stop7h 49m
JetBlue
Fri 9/183:59 pm
SDQ
- ORD
1 stop8h 32m
JetBlue
Deal found 6/7![JetBlue logo]()
$354
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Sat 8/291:34 pm
SDQ
- ORD
1 stop11h 10m
JetBlue
Deal found 6/8![JetBlue logo]()
$355
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- SDQ
1 stop7h 21m
JetBlue
Wed 9/303:59 pm
SDQ
- ORD
1 stop8h 32m
JetBlue
Deal found 6/9![JetBlue logo]()
$356
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Tue 8/184:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/10![JetBlue logo]()
$358
This Arajet deal was found by Cheapflights users on 6/11. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 10/301:40 am
SDQ
- ORD
1 stop9h 17m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:29 am
ORD
- SDQ
1 stop15h 00m
Multiple Airlines
Mon 8/3112:41 pm
SDQ
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$372
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/302:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Tue 9/84:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/11![JetBlue logo]()
$373
This Arajet deal was found by Cheapflights users on 6/12. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 10/91:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 6/10. 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 10/317:00 am
ORD
- SDQ
1 stop7h 16m
JetBlue
Thu 11/126:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$378
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Tue 9/152:56 pm
SDQ
- MDW
1 stop8h 29m
Delta
Deal found 6/12![Delta logo]()
$500
Best flights from Chicago to Santo DomingoDiscover carefully curated flight deals from Chicago to Santo Domingo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2026.
Discover carefully curated flight deals from Chicago to Santo Domingo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 12, 2026.
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:00 am
ORD
- SDQ
1 stop7h 16m
JetBlue
Tue 11/35:28 pm
SDQ
- ORD
1 stop8h 16m
JetBlue
Deal found 6/11![JetBlue logo]()
$378
This Arajet deal was found by Cheapflights users on 6/12. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 8/71:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 6/7. 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 8/246:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 8/292:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/7![Delta logo]()
$512
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:05 am
ORD
- SDQ
2 stops12h 39m
American Airlines
Sat 8/2910:27 am
SDQ
- ORD
1 stop8h 01m
American Airlines
Deal found 6/7![American Airlines logo]()
$517
This Copa Airlines deal was found by Cheapflights users on 6/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:21 pm
ORD
- SDQ
1 stop19h 21m
Copa Airlines
Sun 7/512:43 pm
SDQ
- ORD
1 stop26h 14m
Copa Airlines
Deal found 6/9![Copa Airlines logo]()
$589
This JetBlue deal was found by Cheapflights users on 6/10. 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.
Thu 7/232:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 7/305:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$502
This Delta deal was found by Cheapflights users on 6/11. 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 10/147:10 am
ORD
- SDQ
2 stops10h 14m
Delta
Wed 10/217:49 pm
SDQ
- ORD
2 stops15h 39m
Delta
Deal found 6/11![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:30 am
ORD
- SDQ
1 stop6h 58m
Delta
Mon 8/102:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/9![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 am
ORD
- SDQ
1 stop7h 11m
Delta
Tue 10/277:49 pm
SDQ
- ORD
2 stops15h 39m
Delta
Deal found 6/9![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am
MDW
- SDQ
2 stops11h 01m
Delta
Tue 9/152:56 pm
SDQ
- MDW
1 stop8h 29m
Delta
Deal found 6/12![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Mon 8/242:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/9![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 6/11. 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 7/285:30 am
ORD
- SDQ
1 stop6h 47m
Delta
Thu 8/62:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/11![Delta logo]()
$536
This Delta deal was found by Cheapflights users on 6/7. 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.
Thu 8/205:30 am
ORD
- SDQ
2 stops11h 36m
Delta
Sun 8/232:53 pm
SDQ
- ORD
1 stop10h 04m
Delta
Deal found 6/7![Delta logo]()
$591
This Delta deal was found by Cheapflights users on 6/12. 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 12/28:55 am
ORD
- SDQ
2 stops14h 40m
Delta
Wed 12/96:45 am
SDQ
- ORD
2 stops14h 49m
Delta
Deal found 6/12![Delta logo]()
$595
This Delta deal was found by Cheapflights users on 6/7. 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.
Thu 8/206:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 8/222:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/7![Delta logo]()
$631
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 8/306:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Tue 9/82:37 pm
SDQ
- MDW
1 stop8h 09m
Delta
Deal found 6/10![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 8/186:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Mon 8/312:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/8![Delta logo]()
$713
This Delta deal was found by Cheapflights users on 6/10. 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.
Mon 8/106:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Sat 8/152:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/10![Delta logo]()
$713
This Delta deal was found by Cheapflights users on 6/11. 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 6/276:00 am
MDW
- SDQ
1 stop6h 16m
Delta
Sat 7/46:06 am
SDQ
- MDW
2 stops14h 56m
Delta
Deal found 6/11![Delta logo]()
$718
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
MDW
- SDQ
2 stops11h 25m
Delta
Tue 9/222:56 pm
SDQ
- MDW
1 stop8h 29m
Delta
Deal found 6/11![Delta logo]()
$790
Last-minute flights from Chicago to Santo DomingoDiscover last-minute flight deals from Chicago to Santo Domingo. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santo Domingo. Data last updated June 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/12. 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 6/1612:50 pm
MDW
- SDQ
2 stops10h 52m
Delta
Tue 6/236:06 am
SDQ
- MDW
2 stops13h 25m
Delta
Deal found 6/12![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 6/12. 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 6/276:00 am
MDW
- SDQ
1 stop6h 16m
Delta
Sat 7/46:06 am
SDQ
- MDW
2 stops14h 56m
Delta
Deal found 6/12![Delta logo]()
$631
This Travelocity deal was found by Cheapflights users on 6/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:00 pm
ORD
- SDQ
1 stop14h 06m
Multiple Airlines
Wed 8/194:44 pm
SDQ
- ORD
1 stop8h 00m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$445
This Arajet deal was found by Cheapflights users on 6/7. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Fri 7/171:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$422
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:52 pm
ORD
- SDQ
1 stop13h 11m
Multiple Airlines
Sun 7/125:01 am
SDQ
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$450
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Sun 7/125:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/8![JetBlue logo]()
$429
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sun 7/125:00 am
ORD
- SDQ
1 stop6h 57m
American Airlines
Fri 7/172:20 pm
SDQ
- ORD
1 stop8h 41m
American Airlines
Deal found 6/10![American Airlines logo]()
$380
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Sun 7/265:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/8![JetBlue logo]()
$412
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Tue 7/285:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/9![JetBlue logo]()
$418
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
MDW
- SDQ
1 stop6h 17m
Delta
Sat 8/82:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/9![Delta logo]()
$586
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
Tue 7/282:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 8/65:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/12![JetBlue logo]()
$431
This Faresmojo deal was found by Cheapflights users on 6/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Thu 8/65:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$427
One-way flights from Chicago to Santo DomingoSearch for one-way flight options from Chicago to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
Search for one-way flight options from Chicago to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated June 12, 2026.
This SmartFares deal was found by Cheapflights users on 6/8. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am
ORD
- SDQ
1 stop6h 19m
JetBlue
Deal found 6/8![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 8/712:44 am
ORD
- SDQ
1 stop16h 59m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$163
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/8![JetBlue logo]()
$165
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/92:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/9![JetBlue logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 9/96:00 am
ORD
- SDQ
1 stop6h 34m
JetBlue
Deal found 6/10![JetBlue logo]()
$172
This JetBlue deal was found by Cheapflights users on 6/12. 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 9/87:00 am
ORD
- SDQ
1 stop7h 21m
JetBlue
Deal found 6/12![JetBlue logo]()
$177
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 9/86:45 am
ORD
- SDQ
2 stops10h 59m
American Airlines
Deal found 6/11![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 8/45:00 am
ORD
- SDQ
1 stop6h 57m
American Airlines
Deal found 6/11![American Airlines logo]()
$181
This Arajet deal was found by Cheapflights users on 6/12. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:45 am
ORD
- SDQ
1 stop8h 35m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$193
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/10![JetBlue logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 7/152:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/11![JetBlue logo]()
$201
This JetBlue deal was found by Cheapflights users on 6/12. 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 8/12:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/12![JetBlue logo]()
$206
Find flight deals from Chicago to Santo Domingo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santo Domingo (SDQ). 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 June 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (Faresmojo) |
One-way from | $162 (SmartFares) |
Popular in | December |
Cheapest in | February |
Average price | $674 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Santo Domingo 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 June 12, 2026.
Use the filters below to find and compare flights from Chicago to Santo Domingo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Mon 11/2
7:00 am-4:16 pm
1 stop7h 16m
Santo Domingo Las Americas
Tue 11/3
5:28 pm-11:44 pm
1 stop8h 16m
$378
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Sat 8/1
12:12 pm-9:40 pm
1 stop8h 28m
Santo Domingo Las Americas
Fri 8/7
1:40 am-11:12 am
1 stop10h 32m
$469
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Thu 7/23
2:35 pm-11:59 pm
1 stop8h 24m
Santo Domingo Las Americas
Thu 7/30
5:01 am-1:39 pm
1 stop9h 38m
$502
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Mon 8/24
6:05 am-1:28 pm
1 stop6h 23m
Santo Domingo Las Americas
Sat 8/29
2:53 pm-10:36 pm
1 stop8h 43m
$512
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Mon 8/24
5:05 am-6:44 pm
2 stops12h 39m
Santo Domingo Las Americas
Sat 8/29
10:27 am-5:28 pm
1 stop8h 01m
$517
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 10/14
7:10 am-6:24 pm
2 stops10h 14m
Santo Domingo Las Americas
Wed 10/21
7:49 pm-10:28 am
2 stops15h 39m
$517
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Wed 8/5
5:30 am-1:28 pm
1 stop6h 58m
Santo Domingo Las Americas
Mon 8/10
2:53 pm-7:56 am
2 stops18h 03m
$517
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Thu 10/22
5:30 am-1:41 pm
1 stop7h 11m
Santo Domingo Las Americas
Tue 10/27
7:49 pm-10:28 am
2 stops15h 39m
$517
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sun 9/6
6:05 am-6:06 pm
2 stops11h 01m
Santo Domingo Las Americas
Tue 9/15
2:56 pm-10:25 pm
1 stop8h 29m
$530
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Thu 8/13
6:05 am-1:28 pm
1 stop6h 23m
Santo Domingo Las Americas
Mon 8/24
2:53 pm-10:36 pm
1 stop8h 43m
$531
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Chicago to Santo Domingo
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 Santo Domingo in June.
| 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 | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago-Santo Domingo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santo Domingo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Santo Domingo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Santo Domingo 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-Santo Domingo 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 Santo Domingo
Have a flexible travel schedule? Discover the best time to fly to Santo Domingo from Chicago with our price prediction graph.
CHI-SDQ
ORD-SDQ
MDW-SDQ
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 Santo Domingo
CHI-SDQ
ORD-SDQ
MDW-SDQ
What is the cheapest month to book a flight from Chicago to Santo Domingo?
Currently, January is the cheapest month in which you can book a flight from Chicago to Santo Domingo (average of $84). Flying from Chicago to Santo Domingo in May is currently the most expensive (average of $352). 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 Santo Domingo?
What’s the top layover airport for flights from Chicago to Santo Domingo?
Share of 1-stop round-trip flights from Chicago to Santo Domingo chosen by Cheapflights users in the past 12 months, using the same layover each way.
Miami (MIA) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago to Santo Domingo on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Santo Domingo?
Average round-trip fare for 1-stop flights from Chicago to Santo Domingo, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $387.
What’s the fastest layover option from Chicago to Santo Domingo?
Shortest average travel time for 1-stop one-way flights from Chicago to Santo Domingo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 46m.
Which airport typically offers the quickest layover for flights from Chicago to Santo Domingo?
Average layover duration for 1-stop one-way flights from Chicago to Santo Domingo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Philadelphia (PHL) offer the fastest connection on this route, with an average layover time of 1h 19m.
How far ahead should I book a flight from Chicago to Santo Domingo?
The best time to book flights from Chicago to Santo Domingo is 58 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Santo Domingo
Get insights into the airlines that provide service to Santo Domingo. 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 Santo Domingo. Reviews last updated June 12, 2026.
Read reviews from past customers who have flown Delta,American Airlines, andJetBlue from Chicago to Santo Domingo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Comfort
7.8
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Santo Domingo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Santo Domingo?
Book flights to Santo Domingo if you plan to visit one of these locationsJuan Dolio
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Chicago and Santo Domingo flights
Browse other Chicago and Santo Domingo flight options. Last updated on June 12, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 12, 2026.
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Other flights to Santo Domingo
Explore flights to Santo Domingo departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 12, 2026.
Top 4 airlines flying from Chicago to Santo Domingo
Discover the top 4 airlines that operate flights from Chicago to Santo Domingo. 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 June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$211 | Average$481 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$383 | Average$521 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$402 | Average$557 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$410 | Average$488 | FlexibilityNo cancel fee | On-timeN/A |