$205+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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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 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 October 26, 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 October 26, 2026.
This Arajet deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:40 am -
1 stop10h 30m
Sat 11/1411:10 am -
1 stop8h 30m
Deal found 10/24![Multiple Airlines logo]()
$390
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/196:48 pm -
1 stop8h 45m
Sun 1/312:26 am -
1 stop15h 07m
Deal found 10/26![Frontier logo]()
$429
This Arajet deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:40 am -
1 stop10h 30m
Sat 11/2811:10 am -
1 stop8h 30m
Deal found 10/22![Multiple Airlines logo]()
$437
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:30 am -
2 stops19h 13m
Mon 11/309:20 pm -
1 stop12h 44m
Deal found 10/22![Multiple Airlines logo]()
$443
This JetBlue deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:32 pm -
1 stop11h 04m
Sun 11/157:00 am -
1 stop7h 18m
Deal found 10/26![JetBlue logo]()
$457
This JetBlue deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:20 am -
1 stop14h 38m
Thu 12/317:00 am -
1 stop7h 30m
Deal found 10/24![JetBlue logo]()
$462
This Cheapflightsfares deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/283:26 pm -
1 stop11h 30m
Mon 1/43:17 pm -
1 stop20h 03m
Deal found 10/24![Frontier logo]()
$487
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Fri 11/136:00 am -
1 stop18h 18m
Sun 11/155:00 am -
1 stop8h 06m
Deal found 10/25![United Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Thu 12/31:27 pm -
1 stop9h 02m
Sun 12/65:24 pm -
2 stops15h 54m
Deal found 10/26![Multiple Airlines logo]()
$493
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:41 pm -
2 stops14h 18m
Mon 12/710:37 pm -
2 stops21h 08m
Deal found 10/24![Multiple Airlines logo]()
$494
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:30 am -
3 stops36h 17m
Mon 11/166:42 pm -
2 stops25h 03m
Deal found 10/24![Multiple Airlines logo]()
$509
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:19 am -
2 stops23h 55m
Wed 12/212:28 pm -
2 stops21h 36m
Deal found 10/22![Multiple Airlines logo]()
$579
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 October 26, 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 October 26, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1912:06 pm -
1 stop26h 40m
Tue 1/262:13 pm -
1 stop23h 55m
Deal found 10/22![Copa Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 2/37:35 am -
1 stop16h 17m
Sun 2/75:30 am -
2 stops12h 36m
Deal found 10/25![Delta logo]()
$557
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:00 am -
1 stop10h 15m
Sat 2/610:30 am -
1 stop11h 16m
Deal found 10/21![United Airlines logo]()
$575
This Copa Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/265:50 am -
1 stop8h 56m
Tue 2/22:13 pm -
1 stop18h 49m
Deal found 10/22![Copa Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 1/283:49 pm -
1 stop10h 06m
Sun 1/316:00 am -
1 stop6h 24m
Deal found 10/25![Delta logo]()
$557
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/176:00 am -
1 stop11h 13m
Fri 11/2711:56 am -
1 stop9h 50m
Deal found 10/26![United Airlines logo]()
$577
This Copa Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 2/37:02 pm -
1 stop19h 44m
Sun 2/72:13 pm -
1 stop23h 55m
Deal found 10/25![Copa Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 4/212:35 pm -
1 stop10h 15m
Wed 4/286:00 am -
1 stop11h 29m
Deal found 10/25![Delta logo]()
$575
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/33:49 pm -
1 stop10h 06m
Sun 2/76:00 am -
1 stop6h 24m
Deal found 10/26![Delta logo]()
$610
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/229:35 pm -
2 stops17h 26m
Mon 1/256:00 am -
2 stops12h 06m
Deal found 10/26![Delta logo]()
$700
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 10/26![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/247:30 am -
2 stops13h 07m
Wed 3/36:00 am -
2 stops11h 20m
Deal found 10/22![Delta logo]()
$724
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/177:02 am -
2 stops13h 02m
Fri 11/276:00 am -
1 stop6h 32m
Deal found 10/26![Delta logo]()
$774
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/23:40 pm -
1 stop8h 30m
Tue 3/96:00 am -
1 stop6h 10m
Deal found 10/24![Delta logo]()
$819
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/287:30 am -
2 stops13h 07m
Thu 2/49:55 am -
2 stops12h 35m
Deal found 10/22![Delta logo]()
$853
Last-minute flights from Santo Domingo to ChicagoDiscover last-minute flight deals from Santo Domingo to Chicago. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Santo Domingo to Chicago. Data last updated October 26, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:10 am -
2 stops13h 37m
Wed 11/116:42 pm -
2 stops26h 30m
Deal found 10/24![Multiple Airlines logo]()
$595
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:19 pm -
1 stop14h 41m
Mon 11/97:50 pm -
1 stop14h 09m
Deal found 10/22![American Airlines logo]()
$501
This Arajet deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:40 am -
1 stop10h 30m
Sat 11/1411:10 am -
1 stop8h 30m
Deal found 10/24![Multiple Airlines logo]()
$390
This Mytrip deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:30 am -
3 stops36h 17m
Mon 11/166:42 pm -
2 stops25h 03m
Deal found 10/24![Multiple Airlines logo]()
$509
This Copa Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:45 pm -
1 stop26h 01m
Mon 11/167:35 am -
1 stop27h 35m
Deal found 10/22![Copa Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:57 pm -
1 stop8h 57m
Tue 11/176:00 am -
1 stop6h 32m
Deal found 10/22![Delta logo]()
$581
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:19 am -
3 stops27h 06m
Wed 11/186:42 pm -
2 stops26h 30m
Deal found 10/22![Multiple Airlines logo]()
$587
This JetBlue deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:32 pm -
1 stop11h 04m
Sun 11/157:00 am -
1 stop7h 18m
Deal found 10/26![JetBlue logo]()
$457
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Fri 11/136:00 am -
1 stop18h 18m
Sun 11/155:00 am -
1 stop8h 06m
Deal found 10/25![United Airlines logo]()
$492
This Arajet deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:40 am -
1 stop10h 30m
Sat 11/2811:10 am -
1 stop8h 30m
Deal found 10/22![Multiple Airlines logo]()
$437
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:30 am -
2 stops19h 13m
Mon 11/309:20 pm -
1 stop12h 44m
Deal found 10/22![Multiple Airlines logo]()
$443
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:19 am -
2 stops23h 55m
Wed 12/212:28 pm -
2 stops21h 36m
Deal found 10/22![Multiple Airlines logo]()
$579
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 October 26, 2026.
Search for one-way flight options from Santo Domingo to Chicago. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Trip.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Air Canada logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Thu 12/32:33 pm -
1 stop12h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Thu 12/32:33 pm -
1 stop26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$212
This Arajet deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/142:05 pm -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$219
This Kissandfly.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:27 pm -
1 stop9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:30 am -
2 stops40h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:30 am -
2 stops30h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$242
This Frontier deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:35 pm -
1 stop9h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/11:27 pm -
2 stops26h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$253
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:55 pm -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/212:41 pm -
2 stops29h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/212:59 pm -
2 stops10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$260
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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $390 (Arajet) |
One-way from | $205 (Trip.com) |
Popular in | March |
Cheapest in | February |
Average price | $581 |
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 October 26, 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
Fri 12/11
12:15 pm-3:02 pm
1 stop28h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$205
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 11/6
1:40 am-10:10 am
1 stop10h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$219
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 1/14
2:05 pm-10:40 pm
1 stop10h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$219
Santo DomingoChicago
SDQ Santo Domingo Las Americas - MDW Chicago Midway
SDQMDW
Santo Domingo Las Americas
Thu 12/3
2:33 pm-2:41 pm
1 stop26h 08m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$233
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Wed 12/2
7:00 am-9:41 pm
1 stop16h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$256
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 12/3
6:00 am-4:00 pm
2 stops12h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$260
Santo DomingoChicago
SDQ Santo Domingo Las Americas - MDW Chicago Midway
SDQMDW
Santo Domingo Las Americas
Tue 12/1
1:27 pm-4:07 pm
2 stops52h 40m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$266
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Wed 11/25
2:53 pm-12:01 am
1 stop11h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$268
Santo DomingoChicago
SDQ Santo Domingo Las Americas - MDW Chicago Midway
SDQMDW
Santo Domingo Las Americas
Fri 1/22
10:19 am-11:46 pm
2 stops39h 27m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$294
Quickest round-trip
Santo DomingoChicago
SDQ Santo Domingo Las Americas - MDW Chicago Midway
SDQMDW
Santo Domingo Las Americas
Fri 12/4
3:57 pm-10:54 pm
1 stop8h 57m
Chicago Midway
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$301
Showing 1-10 of 31 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | 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 $410 and $684 in November.The cheapest round-trip price found within the last 5 days was $390 on Multiple Airlines (Nov 6-Nov 14).
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 October 26, 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.
Food
6.4
Entertainment
6.8
Comfort
7.1
Overall
7.0
Boarding
7.4
Crew
7.9
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Food
6.4
Entertainment
6.8
Comfort
7.1
Overall
7.0
Boarding
7.4
Crew
7.9
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 26, 2026.
Complete your trip
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Santo Domingo and Chicago flights
Browse other Santo Domingo and Chicago flight options. Last updated on October 26, 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 October 26, 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 October 26, 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% |