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$202+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Jul 8 — Jul 151
Wed 7/8
Wed 7/15
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 June 8, 2026.

This Arajet deal was found by Cheapflights users on 6/3. 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 10/223:30 pm
SDQ
-
ORD
1 stop9h 10m
Multiple Airlines
Mon 10/264:30 am
ORD
-
SDQ
1 stop11h 25m
Multiple Airlines
Deal found 6/3$350
This Arajet deal was found by Cheapflights users on 6/3. 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
SDQ
-
ORD
1 stop9h 15m
Multiple Airlines
Sat 10/3111:27 am
ORD
-
SDQ
1 stop9h 13m
Multiple Airlines
Deal found 6/3$369
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/244:38 pm
SDQ
-
ORD
1 stop8h 06m
JetBlue
Sat 8/222:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/3$375
This Expedia deal was found by Cheapflights users on 6/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:35 pm
SDQ
-
ORD
1 stop11h 09m
JetBlue
Fri 7/172:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/5$386
This Arajet deal was found by Cheapflights users on 6/5. 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 8/203:30 pm
SDQ
-
ORD
1 stop9h 10m
Multiple Airlines
Mon 8/315:30 am
ORD
-
SDQ
1 stop10h 25m
Multiple Airlines
Deal found 6/5$388
This Cheapflightsfares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:44 pm
SDQ
-
ORD
1 stop8h 00m
JetBlue
Sun 9/207:00 am
ORD
-
SDQ
1 stop7h 16m
JetBlue
Deal found 6/4$393
This Expedia deal was found by Cheapflights users on 6/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:01 am
SDQ
-
ORD
1 stop9h 38m
JetBlue
Mon 7/202:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/5$394
This JetBlue deal was found by Cheapflights users on 6/3. 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 9/161:32 pm
SDQ
-
ORD
1 stop11h 12m
JetBlue
Sat 9/192:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/3$398
This Cheapflightsfares deal was found by Cheapflights users on 6/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:01 am
SDQ
-
ORD
1 stop9h 38m
JetBlue
Thu 8/62:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/6$405
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:01 am
SDQ
-
ORD
1 stop9h 38m
JetBlue
Sat 8/87:00 am
ORD
-
SDQ
1 stop7h 21m
JetBlue
Deal found 6/3$409
This Justfly.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:28 pm
SDQ
-
ORD
1 stop8h 16m
JetBlue
Mon 11/92:35 pm
ORD
-
SDQ
1 stop8h 24m
JetBlue
Deal found 6/7$410
This Arajet deal was found by Cheapflights users on 6/5. 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 8/71:40 am
SDQ
-
ORD
1 stop10h 32m
Multiple Airlines
Sat 8/1512:12 pm
ORD
-
SDQ
1 stop8h 28m
Multiple Airlines
Deal found 6/5$416

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 June 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$350
(Arajet)

One-way from

$202
(SmartFares)

Popular in

May

Cheapest in

February

Average price

$501
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. 6% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 8, 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 10/22

3:30 pm-11:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 10/26

4:30 am-4:55 pm

1 stop11h 25m

$350

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 11/1

2:28 pm-11:44 pm

1 stop11h 16m

Chicago O'Hare Intl

Wed 11/4

7:00 am-4:16 pm

1 stop7h 16m

$569

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 8/26

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Sat 8/29

6:51 am-6:06 pm

2 stops10h 15m

$585

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 8/27

2:53 pm-7:56 am

2 stops18h 03m

Chicago O'Hare Intl

Tue 9/1

5:28 am-6:06 pm

2 stops11h 38m

$585

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/5

3:56 pm-9:45 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 11/9

11:10 am-1:35 am

2 stops12h 25m

$596

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 10/19

7:49 pm-10:04 am

1 stop15h 15m

Chicago O'Hare Intl

Sat 10/24

7:10 am-6:24 pm

2 stops10h 14m

$596
Quickest round-trip

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 11/5

3:56 pm-9:45 pm

1 stop7h 49m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$596

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 8/26

2:53 pm-10:36 pm

1 stop8h 43m

Chicago Midway

Sun 9/6

6:05 am-1:28 pm

1 stop6h 23m

$596

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 9/8

2:37 pm-9:46 pm

1 stop8h 09m

Chicago Midway

Sun 9/20

6:05 am-1:41 pm

1 stop6h 36m

$694

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 8/25

6:05 am-6:33 pm

2 stops13h 28m

Chicago Midway

Sat 9/5

6:05 am-6:06 pm

2 stops11h 01m

$756

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 27 resultsSorted by cheapest first
1
2
3

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 June.
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, August is the cheapest month in which you can book a flight from Santo Domingo to Chicago (average of $139). Flying from Santo Domingo to Chicago in July is currently the most expensive (average of $411). 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?

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 June 8, 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
11,640 reviews

Overall

7.1

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

7.9

Food

6.4

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
11,640 reviews
American Airlines
7.1
Good
11,640 reviews

Overall

7.1

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Crew

7.9

Food

6.4

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. 1 airline 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 11h 16m. Santo Domingo and Chicago are separated by a distance of 1947 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Santo Domingo to Chicago round-trip?

    Our cheapest airline available from Santo Domingo to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $468 on this airline. American Airlines is currently priced 4% 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 Copa Airlines, with prices starting from $220 and $237, 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, August is the cheapest month in which you can book a flight from Santo Domingo to Chicago (average of $139). Flying from Santo Domingo to Chicago in July is currently the most expensive (average of $411). 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
Hammond
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.
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights

Top airline flying from Santo Domingo to Chicago

Discover the top airline 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 June 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$468Average$570FlexibilityNo cancel feeOn-time71%

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