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$183+ Cheap flights from Santo Domingo (SDQ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheap flight deals from Santo Domingo to Chicago

Cheapest flights from Santo Domingo to Chicago
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 July 25, 2026.

This Arajet deal was found by Cheapflights users on 7/22. 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 9/173:30 pm
SDQ
-
ORD
1 stop9h 10m
Multiple Airlines
Fri 12/115:45 am
ORD
-
SDQ
1 stop8h 35m
Multiple Airlines
Deal found 7/22$327
This Arajet deal was found by Cheapflights users on 7/21. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:30 pm
SDQ
-
ORD
1 stop9h 10m
Multiple Airlines
Sat 9/1912:12 pm
ORD
-
SDQ
1 stop8h 28m
Multiple Airlines
Deal found 7/21$372
This Arajet deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:30 pm
SDQ
-
ORD
1 stop9h 10m
Multiple Airlines
Mon 9/285:30 am
ORD
-
SDQ
1 stop10h 25m
Multiple Airlines
Deal found 7/20$388
This Arajet deal was found by Cheapflights users on 7/24. 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 8/141:40 am
SDQ
-
ORD
1 stop10h 32m
Multiple Airlines
Sat 8/2912:12 pm
ORD
-
SDQ
1 stop8h 28m
Multiple Airlines
Deal found 7/24$451
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:15 pm
SDQ
-
ORD
1 stop8h 23m
American Airlines
Sat 9/196:59 am
ORD
-
SDQ
1 stop7h 18m
American Airlines
Deal found 7/20$457
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:20 pm
SDQ
-
ORD
1 stop9h 01m
United Airlines
Mon 9/289:35 pm
ORD
-
SDQ
1 stop13h 20m
United Airlines
Deal found 7/20$458
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:27 am
SDQ
-
ORD
1 stop13h 04m
American Airlines
Fri 8/286:59 pm
ORD
-
SDQ
1 stop17h 23m
American Airlines
Deal found 7/20$467
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:30 pm
SDQ
-
ORD
1 stop8h 57m
Multiple Airlines
Sun 9/136:50 am
ORD
-
SDQ
2 stops32h 39m
Multiple Airlines
Deal found 7/23$471
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Sun 11/12:54 pm
SDQ
-
ORD
1 stop10h 36m
American Airlines
Sat 11/79:11 pm
ORD
-
SDQ
1 stop14h 43m
American Airlines
Deal found 7/22$473
This American Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/231:57 pm
SDQ
-
ORD
1 stop11h 32m
American Airlines
Tue 7/286:59 am
ORD
-
SDQ
1 stop10h 41m
American Airlines
Deal found 7/20$475
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/2710:27 am
SDQ
-
ORD
1 stop15h 08m
American Airlines
Thu 10/18:42 am
ORD
-
SDQ
1 stop8h 52m
American Airlines
Deal found 7/22$476
This Delta deal was found by Cheapflights users on 7/24. 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.
Thu 11/53:56 pm
SDQ
-
MDW
1 stop8h 29m
Delta
Mon 11/99:30 am
MDW
-
SDQ
2 stops14h 05m
Delta
Deal found 7/24$557

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(Arajet)

One-way from

$183
(Arajet)

Popular in

March

Cheapest in

February

Average price

$551
Provider with most accurate pricing for Santo Domingo Las Americas-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Santo Domingo Las Americas-Chicago (CHI) flights.
Search Deals
From Santo Domingo Las Americas to Chicago (CHI)
Search Deals
One-way flight from Santo Domingo Las Americas to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 2,558,603 searches. Data last updated July 25, 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

Price

Cheapest round-trip

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 9/24

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 9/28

5:30 am-4:55 pm

1 stop10h 25m

$388

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/5

4:59 pm-12:44 am

1 stop9h 45m

Chicago O'Hare Intl

Mon 11/9

7:50 pm-11:59 am

1 stop14h 09m

$467

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 8/14

1:40 am-11:12 am

1 stop10h 32m

Chicago O'Hare Intl

Sat 8/22

12:12 pm-9:40 pm

1 stop8h 28m

$486

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/27

2:22 pm-11:52 pm

2 stops10h 30m

Chicago O'Hare Intl

Sun 8/30

6:00 am-1:22 pm

1 stop6h 22m

$519

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/5

2:24 pm-12:46 pm

1 stop24h 22m

Chicago O'Hare Intl

Mon 11/9

2:13 pm-4:12 pm

1 stop23h 59m

$521

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 9/7

12:12 pm-1:02 am

1 stop13h 50m

Chicago O'Hare Intl

Fri 9/11

8:01 am-11:42 am

1 stop26h 41m

$521

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 9/24

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Mon 9/28

5:30 am-6:07 pm

2 stops11h 37m

$557

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 11/5

3:56 pm-10:25 pm

1 stop8h 29m

Chicago Midway

Mon 11/9

9:30 am-1:35 am

2 stops14h 05m

$557

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 9/9

2:53 pm-10:44 pm

1 stop8h 51m

Chicago Midway

Thu 9/17

6:05 am-1:27 pm

1 stop6h 22m

$557

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 11/25

7:19 pm-7:55 am

1 stop14h 36m

Chicago O'Hare Intl

Fri 12/11

7:37 pm-2:00 pm

1 stop16h 23m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 36 resultsSorted by cheapest first
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4

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 July.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

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 $801). 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 $480 and $562 in September.
The cheapest round-trip price found within the last 5 days was $327 on Multiple Airlines (Sep 17-Dec 11).

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 July 25, 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.
American Airlines
7.1
Good
11,847 reviews

Overall

7.1

Crew

7.9

Boarding

7.5

Food

6.4

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,847 reviews
American Airlines
7.1
Good
11,847 reviews

Overall

7.1

Crew

7.9

Boarding

7.5

Food

6.4

Comfort

7.2

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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.

  • What airport do you fly from for flights from Santo Domingo to Chicago?

    Santo Domingo Las Americas (SDQ), located 17.5 mi from the city center, is the airport you fly out of when you book flights from Santo Domingo to Chicago. 2 airlines have flights from Las Americas to Chicago on a regular basis. Booking flights from Santo Domingo Las Americas to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Santo Domingo to Chicago?

    Departing from Santo Domingo to Chicago will take you 8h 29m. Santo Domingo and Chicago are separated by a distance of 1932 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Santo Domingo to Chicago round-trip?

    Our cheapest airline available from Santo Domingo to Chicago is JetBlue. Our recent data shows that you can find tickets from as low as $375 on this airline. An additional option worth looking into is American Airlines, starting at $468. JetBlue is currently priced 27% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Santo Domingo to Chicago one-way?

    $217 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $220 and $238, respectively.

  • Can I find deals for flights from Santo Domingo to Chicago that include hotel bookings?

    Yes. In addition to deals on Santo Domingo to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Santo Domingo to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Santo Domingo to Chicago.

  • Can I find deals for business class flights from Santo Domingo to Chicago?

    Yes. Cheapflights offers flight deals from Santo Domingo to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $801). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
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Porter

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Alternative routes for Santo Domingo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights

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 2,558,603 searches. Data last updated July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$375Average$383FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$468Average$582FlexibilityNo cancel feeOn-time71%

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