$186+ Cheap flights from Santo Domingo (SDQ) to Chicago (CHI)
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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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 Santo Domingo to ChicagoExplore the most affordable flight options available from Santo Domingo to Chicago. 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 Santo Domingo to Chicago. 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 9/9. 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.
Thu 11/122:05 pm -
1 stop10h 35m
Sun 11/153:20 am -
1 stop11h 25m
Deal found 9/9![Multiple Airlines logo]()
$347
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.
Sun 10/251:55 pm -
1 stop9h 15m
Sat 10/3111:27 am -
1 stop9h 13m
Deal found 9/10![Multiple Airlines logo]()
$366
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.
Sun 10/181:55 pm -
1 stop9h 15m
Sat 10/3111:27 am -
1 stop9h 13m
Deal found 9/7![Multiple Airlines logo]()
$427
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:19 pm -
1 stop18h 52m
Tue 12/82:50 pm -
1 stop8h 01m
Deal found 9/7![Multiple Airlines logo]()
$495
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:29 pm -
1 stop30h 04m
Thu 12/36:15 am -
1 stop10h 49m
Deal found 9/7![Frontier logo]()
$497
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.
Thu 9/101:45 pm -
1 stop10h 55m
Mon 9/145:30 am -
1 stop10h 25m
Deal found 9/7![Multiple Airlines logo]()
$509
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:19 pm -
1 stop18h 52m
Thu 12/106:15 am -
1 stop10h 49m
Deal found 9/7![Frontier logo]()
$517
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.
Thu 11/512:10 pm -
1 stop14h 01m
Mon 11/92:13 pm -
1 stop9h 55m
Deal found 9/11![Copa Airlines logo]()
$526
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.
Thu 10/81:45 pm -
1 stop10h 55m
Mon 10/125:30 am -
1 stop10h 25m
Deal found 9/8![Multiple Airlines logo]()
$531
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/248:19 pm -
1 stop24h 43m
Thu 12/318:07 pm -
1 stop20h 57m
Deal found 9/6![Frontier logo]()
$545
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.
Wed 11/117:02 am -
2 stops13h 02m
Wed 11/1811:27 am -
2 stops12h 47m
Deal found 9/9![Delta logo]()
$557
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.
Wed 12/238:19 pm -
1 stop24h 43m
Wed 12/308:07 pm -
1 stop20h 57m
Deal found 9/10![Frontier logo]()
$576
Best flights from Santo Domingo to ChicagoDiscover carefully curated flight deals from Santo Domingo to Chicago 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 Santo Domingo to Chicago 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 9/9. 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 11/512:10 pm -
1 stop14h 01m
Thu 11/122:13 pm -
1 stop20h 57m
Deal found 9/9![Copa Airlines logo]()
$526
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:10 pm -
1 stop9h 22m
Thu 10/226:00 am -
1 stop15h 46m
Deal found 9/11![United Airlines logo]()
$548
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.
Wed 9/307:35 pm -
2 stops16h 02m
Sat 10/36:00 am -
1 stop10h 29m
Deal found 9/8![Delta logo]()
$557
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.
Mon 11/232:24 pm -
1 stop11h 47m
Mon 11/302:13 pm -
1 stop21h 01m
Deal found 9/10![Copa Airlines logo]()
$526
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:10 pm -
1 stop9h 22m
Sat 10/316:59 am -
1 stop14h 47m
Deal found 9/7![United Airlines logo]()
$553
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.
Thu 11/512:10 pm -
1 stop14h 01m
Mon 11/92:13 pm -
1 stop9h 55m
Deal found 9/11![Copa Airlines logo]()
$526
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 pm -
2 stops18h 12m
Mon 10/266:04 am -
1 stop6h 28m
Deal found 9/11![Delta logo]()
$588
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop15h 13m
Tue 10/278:40 pm -
1 stop16h 26m
Deal found 9/9![United Airlines logo]()
$562
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.
Fri 10/2312:42 pm -
1 stop26h 17m
Sun 10/258:35 am -
1 stop27h 37m
Deal found 9/11![Copa Airlines logo]()
$526
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:57 pm -
1 stop8h 36m
Wed 10/286:04 am -
2 stops11h 02m
Deal found 9/11![Delta logo]()
$612
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/174:18 pm -
1 stop26h 03m
Mon 11/309:36 pm -
2 stops14h 05m
Deal found 9/9![United Airlines logo]()
$568
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 10/2912:12 pm -
1 stop13h 53m
Thu 11/52:13 pm -
1 stop20h 57m
Deal found 9/10![Copa Airlines logo]()
$544
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 9/307:35 pm -
2 stops14h 32m
Wed 10/76:04 am -
1 stop6h 28m
Deal found 9/7![Delta logo]()
$628
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 11/2412:45 pm -
1 stop13h 26m
Tue 12/12:13 pm -
1 stop24h 00m
Deal found 9/9![Copa Airlines logo]()
$544
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.
Wed 9/307:35 pm -
2 stops14h 32m
Sat 10/36:05 am -
1 stop6h 22m
Deal found 9/8![Delta logo]()
$628
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:57 pm -
1 stop8h 36m
Mon 11/96:00 am -
1 stop6h 32m
Deal found 9/11![Delta logo]()
$628
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.
Sat 10/312:12 pm -
1 stop26h 47m
Sat 10/108:01 am -
1 stop17h 24m
Deal found 9/10![Copa Airlines logo]()
$573
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.
Tue 10/62:57 pm -
1 stop8h 36m
Tue 10/136:04 am -
1 stop6h 28m
Deal found 9/8![Delta logo]()
$628
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:57 pm -
1 stop8h 36m
Sun 10/256:04 am -
1 stop6h 28m
Deal found 9/11![Delta logo]()
$628
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.
Thu 12/33:57 pm -
1 stop8h 58m
Tue 12/86:00 am -
2 stops11h 28m
Deal found 9/7![Delta logo]()
$628
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.
Sun 1/313:40 pm -
1 stop8h 30m
Sun 2/76:00 am -
2 stops11h 20m
Deal found 9/9![Delta logo]()
$700
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.
Tue 9/292:53 pm -
1 stop8h 51m
Tue 10/66:04 am -
1 stop6h 28m
Deal found 9/8![Delta logo]()
$795
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.
Tue 9/222:53 pm -
1 stop8h 51m
Tue 9/296:05 am -
1 stop6h 22m
Deal found 9/8![Delta logo]()
$795
Last-minute flights from Santo Domingo to ChicagoDiscover last-minute flight deals from Santo Domingo to Chicago. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Santo Domingo to Chicago. Data last updated September 11, 2026 and is based on user searches.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:20 pm -
1 stop9h 01m
Wed 10/149:35 pm -
1 stop13h 20m
Deal found 9/8![United Airlines logo]()
$538
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.
Thu 10/81:45 pm -
1 stop10h 55m
Mon 10/125:30 am -
1 stop10h 25m
Deal found 9/8![Multiple Airlines logo]()
$531
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.
Mon 10/122:16 pm -
1 stop11h 41m
Mon 10/193:20 pm -
1 stop20h 52m
Deal found 9/10![Copa Airlines logo]()
$550
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.
Fri 10/168:47 am -
1 stop17h 10m
Sun 10/258:35 am -
1 stop27h 37m
Deal found 9/10![Copa Airlines logo]()
$526
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:10 pm -
1 stop11h 11m
Thu 10/2910:39 am -
1 stop11h 07m
Deal found 9/7![United Airlines logo]()
$553
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.
Sun 10/181:55 pm -
1 stop9h 15m
Sat 10/3111:27 am -
1 stop9h 13m
Deal found 9/7![Multiple Airlines logo]()
$427
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:50 pm -
1 stop27h 30m
Sat 10/2411:20 pm -
1 stop11h 30m
Deal found 9/11![Avianca logo]()
$554
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop18h 21m
Sun 10/255:00 am -
1 stop8h 06m
Deal found 9/11![United Airlines logo]()
$548
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.
Sun 10/251:55 pm -
1 stop9h 15m
Sat 10/3111:27 am -
1 stop9h 13m
Deal found 9/10![Multiple Airlines logo]()
$366
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:35 pm -
1 stop9h 55m
Tue 11/39:00 am -
2 stops8h 53m
Deal found 9/6![American Airlines logo]()
$541
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:07 pm -
1 stop30h 58m
Tue 11/32:13 pm -
1 stop18h 53m
Deal found 9/7![Copa Airlines logo]()
$547
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 10/2912:12 pm -
1 stop13h 53m
Thu 11/52:13 pm -
1 stop20h 57m
Deal found 9/10![Copa Airlines logo]()
$544
One-way flights from Santo Domingo to ChicagoSearch for one-way flight options from Santo Domingo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
Search for one-way flight options from Santo Domingo to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Arajet deal was found by Cheapflights users on 9/8. 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.
Fri 11/201:40 am -
1 stop9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$186
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.
Thu 9/243:30 pm -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$199
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:40 am -
1 stop10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$228
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:15 pm -
1 stop28h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Air Canada logo]()
$241
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.
Fri 9/251:40 am -
1 stop10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$247
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:19 pm -
1 stop24h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$250
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/138:19 pm -
1 stop24h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$252
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:19 pm -
1 stop18h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$256
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:19 pm -
1 stop18h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$258
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1812:15 pm -
1 stop24h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Air Canada logo]()
$259
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2312:41 pm -
1 stop11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$263
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.
Thu 9/171:45 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$267
Find flight deals from Santo Domingo to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Santo Domingo (SDQ) to Chicago (CHI). 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 | $347 (Arajet) |
One-way from | $186 (Arajet) |
Popular in | March |
Cheapest in | February |
Average price | $486 |
Cheapflights Fare Finder
Customize your flight search to find flights from Santo Domingo to Chicago 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 Santo Domingo to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 11/19
2:05 pm-10:40 pm
1 stop10h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$199
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 9/24
3:30 pm-11:40 pm
1 stop9h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$199
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 10/9
1:40 am-11:12 am
1 stop10h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$228
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 9/25
1:40 am-11:12 am
1 stop10h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$247
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Sun 12/13
3:57 pm-11:52 pm
1 stop9h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$300
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 2/11
7:30 am-8:37 pm
2 stops15h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Tue 9/29
7:35 pm-9:27 am
1 stop14h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Mon 10/5
7:35 pm-9:27 am
1 stop14h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Tue 2/9
7:30 am-4:37 pm
2 stops11h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Wed 2/10
7:30 am-5:34 pm
1 stop12h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Santo Domingo to Chicago
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 Santo Domingo to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Santo Domingo-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santo Domingo-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Santo Domingo-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Santo Domingo-Chicago 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 Santo Domingo-Chicago 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 Santo Domingo to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Santo Domingo with our price prediction graph.
SDQ-CHI
SDQ-ORD
SDQ-MDW
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 Santo Domingo to Chicago
SDQ-CHI
SDQ-ORD
SDQ-MDW
What is the cheapest month to book a flight from Santo Domingo to Chicago?
Currently, February is the cheapest month in which you can book a flight from Santo Domingo to Chicago (average of $384). Flying from Santo Domingo to Chicago in March is currently the most expensive (average of $839). 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 Santo Domingo to Chicago?
Airfare is below average for this route at the moment.
Santo Domingo to Chicago flights typically cost between $367 and $547 in November.The cheapest round-trip price found within the last 5 days was $347 on Multiple Airlines (Nov 12-Nov 15).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2026.
Peruse reviews from past customers who have flown with American Airlines from Santo Domingo to Chicago 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.
Entertainment
6.8
Boarding
7.4
Overall
7.1
Food
6.4
Crew
7.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Entertainment
6.8
Boarding
7.4
Overall
7.1
Food
6.4
Crew
7.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Related info for your journey
Find useful and relevant information for your journey from Santo Domingo to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
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Porter
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Other flights to Chicago
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Santo Domingo and Chicago flights
Browse other Santo Domingo and Chicago flight options. Last updated on September 11, 2026.
Other flights from Santo Domingo
Browse through other flights departing from Santo Domingo. Flights are based on user searches made on Cheapflights and were last updated on September 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Santo Domingo to Chicago
Discover the top 2 airlines that operate flights from Santo Domingo to Chicago. 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$375 | Average$411 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$483 | Average$662 | FlexibilityNo cancel fee | On-time71% |