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$139+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This Travelocity deal was found by Cheapflights users on 2/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Wed 3/115:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 2/1$236
This Booking.com deal was found by Cheapflights users on 2/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/213:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Tue 2/245:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 2/1$260
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Wed 3/48:16 pm
ORD
-
SDQ
1 stop16h 04m
Spirit Airlines
Deal found 2/3$275
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Mon 3/25:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 2/3$276
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Fri 2/203:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Mon 2/235:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 2/2$278
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/162:52 am
SDQ
-
ORD
1 stop9h 25m
Spirit Airlines
Tue 3/245:05 am
ORD
-
SDQ
1 stop7h 10m
Spirit Airlines
Deal found 2/3$281
This Expedia deal was found by Cheapflights users on 2/1. 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.
Sat 3/73:32 pm
SDQ
-
ORD
1 stop7h 41m
Spirit Airlines
Wed 3/186:10 pm
ORD
-
SDQ
1 stop6h 28m
Spirit Airlines
Deal found 2/1$287
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/162:52 am
SDQ
-
ORD
1 stop8h 44m
Multiple Airlines
Tue 3/245:05 am
ORD
-
SDQ
1 stop7h 10m
Multiple Airlines
Deal found 2/1$288
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:11 pm
SDQ
-
ORD
1 stop8h 36m
Multiple Airlines
Sat 2/288:16 pm
ORD
-
SDQ
1 stop16h 04m
Multiple Airlines
Deal found 2/3$311
This Expedia deal was found by Cheapflights users on 2/2. 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 4/293:37 pm
SDQ
-
ORD
1 stop9h 04m
Spirit Airlines
Mon 5/45:15 am
ORD
-
SDQ
1 stop8h 17m
Spirit Airlines
Deal found 2/2$315
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
Wed 2/183:32 pm
SDQ
-
ORD
1 stop10h 15m
Spirit Airlines
Sat 2/285:15 am
ORD
-
SDQ
1 stop7h 05m
Spirit Airlines
Deal found 2/2$317
This eDestinos deal was found by Cheapflights users on 2/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:11 pm
SDQ
-
MDW
2 stops31h 56m
Frontier
Sat 2/286:25 am
MDW
-
SDQ
2 stops25h 14m
Frontier
Deal found 2/3$403

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(Travelocity)

One-way from

$139
(Travelocity)

Popular in

March

Cheapest in

February

Average price

$408
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. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 3, 2026.
Use the filters below to find and compare flights from Santo Domingo to Chicago that are best for you.

Fly from

Santo Domingo

Fly to

Chicago

Route

Depart

Return

Price

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 3/4

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Wed 3/11

5:15 am-1:20 pm

1 stop7h 05m

$236

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sat 2/21

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Tue 2/24

5:15 am-2:20 pm

1 stop7h 05m

$260

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 3/4

3:32 pm-9:13 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 3/18

6:10 pm-1:38 am

1 stop6h 28m

$275

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 2/26

3:32 pm-9:13 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 3/2

8:16 pm-2:20 pm

1 stop16h 04m

$276

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sat 3/7

3:32 pm-9:13 pm

1 stop7h 41m

Chicago O'Hare Intl

Wed 3/18

6:10 pm-1:38 am

1 stop6h 28m

$287

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 2/18

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Sat 2/28

5:15 am-2:20 pm

1 stop7h 05m

$317

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 2/20

3:32 pm-11:47 pm

1 stop10h 15m

Chicago O'Hare Intl

Mon 2/23

6:51 pm-2:20 pm

2 stops17h 29m

$320

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 3/12

2:20 pm-11:17 pm

1 stop9h 57m

Chicago O'Hare Intl

Wed 3/25

6:10 pm-1:38 am

1 stop6h 28m

$323

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 3/19

6:10 am-1:02 pm

1 stop7h 52m

Chicago Midway

Thu 3/26

7:30 am-5:31 am

1 stop21h 01m

$464

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 2/25

3:42 pm-10:31 pm

1 stop8h 49m

Chicago Midway

Wed 3/4

10:49 am-12:32 am

2 stops11h 43m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 29 results
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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 February.
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 $482). 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.

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 February 3, 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
7.2
Good
11,216 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

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
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

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. 3 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 49m. 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $189 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $191 and $468 round-trip. Spirit Airlines is currently priced 62% 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 United Airlines and Copa Airlines, with prices starting from $220 and $225, 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 $482). 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.
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Santo Domingo to O'Hare Intl flights
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Santo Domingo to Midway flights
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Top 3 airlines flying from Santo Domingo to Chicago

Discover the top 3 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$341FlexibilityNo cancel feeOn-time65%
DeltaCheapest$191Average$714FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$530FlexibilityNo cancel feeOn-time71%

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