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$166+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Apr 27 — May 41
Mon 4/27
Mon 5/4
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 March 28, 2026.

This Expedia deal was found by Cheapflights users on 3/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:08 pm
SDQ
-
MDW
1 stop28h 59m
Frontier
Sat 4/116:30 am
MDW
-
SDQ
1 stop6h 26m
Frontier
Deal found 3/23$289
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:35 pm
SDQ
-
ORD
1 stop10h 19m
Multiple Airlines
Fri 5/154:05 pm
ORD
-
SDQ
1 stop20h 24m
Multiple Airlines
Deal found 3/24$328
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Mon 3/232:52 am
SDQ
-
ORD
1 stop8h 44m
Multiple Airlines
Tue 3/314:51 pm
ORD
-
SDQ
1 stop20h 05m
Multiple Airlines
Deal found 3/23$331
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Wed 4/83:01 pm
SDQ
-
ORD
1 stop19h 49m
Multiple Airlines
Sat 4/116:10 pm
ORD
-
SDQ
1 stop6h 28m
Multiple Airlines
Deal found 3/23$343
This Mytrip deal was found by Cheapflights users on 3/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:35 pm
SDQ
-
ORD
1 stop10h 49m
Multiple Airlines
Fri 5/12:20 pm
ORD
-
SDQ
1 stop19h 19m
Multiple Airlines
Deal found 3/25$344
This Expedia deal was found by Cheapflights users on 3/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/511:54 am
SDQ
-
ORD
1 stop20h 40m
Frontier
Sun 4/126:00 am
ORD
-
SDQ
1 stop27h 35m
Frontier
Deal found 3/24$352
This Priceline deal was found by Cheapflights users on 3/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:35 pm
SDQ
-
ORD
1 stop10h 52m
Spirit Airlines
Thu 5/147:45 pm
ORD
-
SDQ
1 stop16h 44m
Spirit Airlines
Deal found 3/23$354
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 4/82:52 am
SDQ
-
ORD
1 stop17h 59m
Multiple Airlines
Sun 4/124:51 pm
ORD
-
SDQ
1 stop20h 05m
Multiple Airlines
Deal found 3/26$356
This Spirit deal was found by Cheapflights users on 3/23. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:35 pm
SDQ
-
ORD
1 stop10h 49m
Spirit Airlines
Wed 4/297:15 pm
ORD
-
SDQ
1 stop17h 14m
Spirit Airlines
Deal found 3/23$367
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Wed 5/1312:41 pm
SDQ
-
ORD
2 stops21h 56m
Multiple Airlines
Sat 5/165:05 am
ORD
-
SDQ
1 stop7h 24m
Multiple Airlines
Deal found 3/23$368
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Fri 4/1710:19 am
SDQ
-
MDW
2 stops13h 07m
Multiple Airlines
Mon 4/207:30 am
MDW
-
SDQ
1 stop20h 59m
Multiple Airlines
Deal found 3/27$453
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/82:52 am
SDQ
-
MDW
2 stops21h 21m
Multiple Airlines
Sun 4/125:05 am
MDW
-
SDQ
1 stop28h 02m
Multiple Airlines
Deal found 3/25$454

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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(Expedia)

One-way from

$166
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$679
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. 2% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 28, 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

Sun 7/19

1:55 pm-10:10 pm

1 stop9h 15m

Chicago O'Hare Intl

Sat 8/1

12:12 pm-9:40 pm

1 stop8h 28m

$519

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 5/12

6:04 am-1:15 am

1 stop20h 11m

Chicago O'Hare Intl

Wed 9/9

8:01 am-2:25 am

1 stop17h 24m

$531

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 5/4

6:05 am-8:40 pm

2 stops15h 35m

Chicago O'Hare Intl

Fri 5/8

6:07 am-6:01 pm

1 stop10h 54m

$560

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 5/12

6:05 am-8:26 pm

2 stops15h 21m

Chicago O'Hare Intl

Thu 9/10

5:30 am-1:41 pm

1 stop7h 11m

$560

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 5/1

2:37 pm-9:25 pm

1 stop7h 48m

Chicago O'Hare Intl

Tue 5/5

8:52 am-12:17 am

2 stops14h 25m

$560

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 5/11

2:49 pm-11:59 pm

1 stop10h 10m

Chicago O'Hare Intl

Wed 9/9

1:30 pm-12:57 am

1 stop10h 27m

$560

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sat 5/9

6:05 am-8:24 pm

2 stops15h 19m

Chicago O'Hare Intl

Wed 5/13

6:07 am-6:01 pm

1 stop10h 54m

$560

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 9/24

2:56 pm-9:46 pm

1 stop7h 50m

Chicago Midway

Mon 9/28

6:00 am-1:41 pm

1 stop6h 41m

$560

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 4/17

2:37 pm-10:28 pm

1 stop8h 51m

Chicago Midway

Mon 4/20

6:00 am-1:12 pm

1 stop6h 12m

$560
Quickest round-trip

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 5/11

2:49 pm-9:09 pm

1 stop7h 20m

Chicago Midway

Wed 9/9

6:00 am-1:12 pm

1 stop6h 12m

$560

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 32 resultsSorted by cheapest first
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2
3
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 June is currently the most expensive (average of $460). 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 March 28, 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
11,520 reviews

Boarding

7.5

Food

6.4

Comfort

7.2

Overall

7.1

Entertainment

6.9

Crew

7.9

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
11,520 reviews
American Airlines
7.1
Good
11,520 reviews

Boarding

7.5

Food

6.4

Comfort

7.2

Overall

7.1

Entertainment

6.9

Crew

7.9

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 15h 35m. Santo Domingo and Chicago are separated by a distance of 1947 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $189 on this airline. An additional option worth looking into is American Airlines, starting at $468. Spirit Airlines is currently priced 60% below the average price you’ll pay for this route.

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

    $151 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $217 and $220, 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 June is currently the most expensive (average of $460). 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
Lansing
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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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$341FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$468Average$530FlexibilityNo cancel feeOn-time71%

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