$158+ Cheap flights from Chicago (CHI) to Santo Domingo (SDQ)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDQ
Oct 11 — Oct 181
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 September 11, 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 September 11, 2026.
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop9h 13m
Fri 11/61:40 am -
1 stop10h 30m
Deal found 9/10![Multiple Airlines logo]()
$343
This Arajet deal was found by Cheapflights users on 9/9. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 am -
1 stop8h 35m
Fri 11/131:40 am -
1 stop9h 17m
Deal found 9/9![Multiple Airlines logo]()
$354
This Arajet deal was found by Cheapflights users on 9/8. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:27 am -
1 stop9h 13m
Fri 11/131:40 am -
1 stop9h 17m
Deal found 9/8![Multiple Airlines logo]()
$355
This Arajet deal was found by Cheapflights users on 9/7. 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 11/2810:27 am -
1 stop9h 13m
Fri 12/41:40 am -
1 stop9h 17m
Deal found 9/7![Multiple Airlines logo]()
$362
This Arajet deal was found by Cheapflights users on 9/7. 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 11/1410:27 am -
1 stop9h 13m
Fri 11/201:40 am -
1 stop9h 17m
Deal found 9/7![Multiple Airlines logo]()
$370
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:12 pm -
1 stop8h 28m
Fri 10/21:40 am -
1 stop10h 32m
Deal found 9/10![Multiple Airlines logo]()
$397
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:15 am -
1 stop10h 49m
Sun 12/138:19 pm -
1 stop18h 52m
Deal found 9/10![Frontier logo]()
$418
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:15 am -
1 stop10h 49m
Thu 12/108:19 pm -
1 stop18h 52m
Deal found 9/8![Frontier logo]()
$419
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
1 stop10h 25m
Sun 10/111:55 pm -
1 stop9h 15m
Deal found 9/10![Multiple Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 11/46:04 am -
1 stop6h 28m
Wed 11/113:57 pm -
1 stop8h 57m
Deal found 9/10![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 11/126:00 am -
2 stops11h 30m
Thu 11/197:02 am -
2 stops13h 02m
Deal found 9/10![Delta logo]()
$532
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 11/176:00 am -
1 stop6h 32m
Tue 11/243:57 pm -
1 stop8h 57m
Deal found 9/9![Delta logo]()
$534
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 September 11, 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 September 11, 2026.
This Copa Airlines deal was found by Cheapflights users on 9/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:01 am -
1 stop26h 40m
Sat 10/3112:12 pm -
1 stop13h 59m
Deal found 9/11![Copa Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:00 am -
1 stop8h 10m
Wed 10/76:00 am -
1 stop11h 34m
Deal found 9/10![United Airlines logo]()
$499
This JetBlue deal was found by Cheapflights users on 9/10. 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 10/82:55 pm -
1 stop10h 09m
Fri 10/235:01 am -
1 stop9h 49m
Deal found 9/10![JetBlue logo]()
$507
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 11/56:04 am -
2 stops11h 02m
Tue 11/103:57 pm -
1 stop8h 57m
Deal found 9/10![Delta logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 9/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:35 am -
1 stop25h 26m
Tue 1/267:05 pm -
1 stop19h 41m
Deal found 9/7![Copa Airlines logo]()
$476
This JetBlue deal was found by Cheapflights users on 9/10. 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.
Wed 10/76:00 am -
1 stop7h 49m
Sun 10/111:32 pm -
1 stop10h 58m
Deal found 9/10![JetBlue logo]()
$508
This Copa Airlines deal was found by Cheapflights users on 9/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm -
1 stop9h 55m
Sun 11/82:24 pm -
1 stop11h 47m
Deal found 9/11![Copa Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 9/6. 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.
Sat 10/246:04 am -
2 stops11h 02m
Mon 11/23:57 pm -
1 stop8h 36m
Deal found 9/6![Delta logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 9/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:20 pm -
1 stop19h 21m
Mon 10/1912:42 pm -
1 stop13h 15m
Deal found 9/10![Copa Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 2/36:00 am -
2 stops11h 20m
Wed 2/103:40 pm -
1 stop8h 30m
Deal found 9/10![Delta logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 9/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:13 pm -
1 stop23h 59m
Mon 11/168:55 am -
1 stop17h 16m
Deal found 9/10![Copa Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 9/7. 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 10/196:04 am -
1 stop6h 28m
Fri 10/232:57 pm -
1 stop8h 36m
Deal found 9/7![Delta logo]()
$540
This Copa Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 12/12:13 pm -
1 stop19h 29m
Fri 12/42:14 pm -
1 stop11h 57m
Deal found 9/9![Copa Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 11/56:04 am -
1 stop6h 28m
Thu 11/127:02 am -
2 stops13h 02m
Deal found 9/10![Delta logo]()
$585
This Copa Airlines deal was found by Cheapflights users on 9/8. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/32:11 pm -
1 stop10h 46m
Wed 3/102:37 pm -
1 stop11h 07m
Deal found 9/8![Copa Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 9/7. 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 9/236:05 am -
1 stop6h 22m
Wed 9/307:35 pm -
2 stops14h 32m
Deal found 9/7![Delta logo]()
$585
This Copa Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 12/22:13 pm -
1 stop9h 55m
Wed 12/98:55 am -
1 stop17h 16m
Deal found 9/9![Copa Airlines logo]()
$484
This Copa Airlines deal was found by Cheapflights users on 9/6. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:01 am -
1 stop17h 24m
Mon 11/28:55 am -
1 stop17h 16m
Deal found 9/6![Copa Airlines logo]()
$484
This Delta deal was found by Cheapflights users on 9/8. 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.
Fri 9/256:05 am -
1 stop6h 22m
Fri 10/27:35 pm -
2 stops16h 01m
Deal found 9/8![Delta logo]()
$613
This Delta deal was found by Cheapflights users on 9/9. 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 10/246:04 am -
1 stop6h 28m
Sat 10/312:57 pm -
1 stop8h 36m
Deal found 9/9![Delta logo]()
$682
This Delta deal was found by Cheapflights users on 9/10. 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.
Thu 11/2612:05 pm -
2 stops11h 29m
Thu 12/37:00 am -
2 stops11h 50m
Deal found 9/10![Delta logo]()
$687
Last-minute flights from Chicago to Santo DomingoDiscover last-minute flight deals from Chicago to Santo Domingo. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Santo Domingo. Data last updated September 11, 2026 and is based on user searches.
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:12 pm -
1 stop8h 28m
Fri 10/21:40 am -
1 stop10h 32m
Deal found 9/10![Multiple Airlines logo]()
$397
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:12 pm -
1 stop8h 28m
Fri 10/91:40 am -
1 stop10h 32m
Deal found 9/10![Multiple Airlines logo]()
$443
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
1 stop10h 25m
Sun 10/111:55 pm -
1 stop9h 15m
Deal found 9/10![Multiple Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 9/10. 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.
Tue 10/66:04 am -
1 stop6h 28m
Fri 10/237:35 pm -
2 stops14h 57m
Deal found 9/10![Delta logo]()
$525
This Delta deal was found by Cheapflights users on 9/6. 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 10/76:04 am -
1 stop6h 28m
Wed 10/142:57 pm -
1 stop8h 36m
Deal found 9/6![Delta logo]()
$540
This Arajet deal was found by Cheapflights users on 9/7. 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 10/1712:12 pm -
1 stop8h 28m
Fri 10/231:40 am -
1 stop10h 32m
Deal found 9/7![Multiple Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 10/216:04 am -
1 stop6h 28m
Wed 10/282:57 pm -
1 stop8h 36m
Deal found 9/10![Delta logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:20 pm -
1 stop10h 05m
Sat 10/3112:12 pm -
1 stop13h 59m
Deal found 9/9![Copa Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:35 am -
1 stop13h 21m
Tue 11/32:24 pm -
1 stop11h 47m
Deal found 9/8![Copa Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:13 pm -
1 stop9h 58m
Wed 11/42:24 pm -
1 stop11h 47m
Deal found 9/8![Copa Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 10/306:04 am -
1 stop6h 28m
Fri 11/68:35 pm -
2 stops16h 02m
Deal found 9/10![Delta logo]()
$532
This Arajet deal was found by Cheapflights users on 9/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop9h 13m
Fri 11/61:40 am -
1 stop10h 30m
Deal found 9/10![Multiple Airlines logo]()
$343
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 September 11, 2026.
Search for one-way flight options from Chicago to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Arajet deal was found by Cheapflights users on 9/11. 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.
Mon 10/55:30 am -
1 stop10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$158
This Arajet deal was found by Cheapflights users on 9/11. 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.
Mon 9/285:30 am -
1 stop10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$177
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:15 am -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$194
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:15 am -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
2 stops33h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:24 am -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$207
This Arajet deal was found by Cheapflights users on 9/11. 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 9/2612:12 pm -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$209
This FlightHub deal was found by Cheapflights users on 9/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:31 pm -
1 stop26h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:24 am -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
2 stops29h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 10/104:41 pm -
2 stops25h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am -
2 stops32h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$217
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $343 (Arajet) |
One-way from | $158 (Arajet) |
Popular in | December |
Cheapest in | February |
Average price | $460 |
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 7,457,451 searches. Data last updated September 11, 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 Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Mon 10/5
5:30 am-4:55 pm
1 stop10h 25m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$158
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Mon 10/26
4:30 am-4:55 pm
1 stop11h 25m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$158
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Thu 10/15
6:00 am-2:10 pm
1 stop7h 10m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$228
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Sun 10/11
7:00 am-2:40 pm
1 stop6h 40m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$228
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Tue 9/29
9:00 am-10:46 pm
1 stop12h 46m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$238
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Wed 1/27
3:45 pm-11:20 pm
1 stop29h 35m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$239
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Sat 1/23
5:45 pm-11:20 pm
1 stop27h 35m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$239
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Sat 10/3
6:00 am-6:34 pm
2 stops11h 34m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$242
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Fri 9/18
6:00 am-10:46 pm
1 stop15h 46m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$242
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Fri 10/23
9:35 pm-11:55 am
1 stop13h 20m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$242
Showing 1-10 of 44 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 September.
| 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 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, November is the cheapest month in which you can book a flight from Chicago to Santo Domingo (average of $385). Flying from Chicago to Santo Domingo in June is currently the most expensive (average of $663). 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?
Airfare is below average for this route at the moment.
Chicago to Santo Domingo flights typically cost between $395 and $540 in October.The cheapest round-trip price found within the last 5 days was $343 on Multiple Airlines (Oct 31-Nov 6).
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 57 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 September 11, 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.
Overall
7.8
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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 September 11, 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 September 11, 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$261 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$354 | Average$457 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$383 | Average$562 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$398 | Average$529 | FlexibilityNo cancel fee | On-time69% |