HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Santo Domingo

$159+ Cheap flights from Chicago (CHI) to Santo Domingo (SDQ)

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 11/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDQ
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Santo Domingo with Cheapflights

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Santo Domingo

Cheapest flights from Chicago to Santo Domingo
Explore the most affordable flight options available from Chicago to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.

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.
Sat 9/1912:12 pm
ORD
-
SDQ
1 stop8h 28m
Multiple Airlines
Sun 9/271:55 pm
SDQ
-
ORD
1 stop9h 15m
Multiple Airlines
Deal found 7/20$421
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 8/66:59 pm
ORD
-
SDQ
1 stop13h 26m
American Airlines
Mon 8/242:22 pm
SDQ
-
ORD
1 stop10h 08m
American Airlines
Deal found 7/20$426
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/155:59 pm
ORD
-
SDQ
1 stop14h 26m
American Airlines
Sat 9/124:20 pm
SDQ
-
ORD
1 stop9h 13m
American Airlines
Deal found 7/19$428
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.
Mon 8/177:03 am
ORD
-
SDQ
2 stops10h 41m
American Airlines
Mon 8/2410:27 am
SDQ
-
ORD
1 stop13h 04m
American Airlines
Deal found 7/20$431
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 9/226:00 am
ORD
-
SDQ
1 stop11h 34m
American Airlines
Tue 10/67:00 am
SDQ
-
ORD
1 stop9h 33m
American Airlines
Deal found 7/18$436
This American Airlines deal was found by Cheapflights users on 7/18. 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 9/237:00 pm
ORD
-
SDQ
1 stop13h 21m
American Airlines
Sun 9/277:34 pm
SDQ
-
ORD
1 stop13h 14m
American Airlines
Deal found 7/18$438
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.
Fri 8/145:05 am
ORD
-
SDQ
2 stops9h 19m
American Airlines
Mon 9/144:20 pm
SDQ
-
ORD
1 stop9h 13m
American Airlines
Deal found 7/22$441
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.
Fri 8/145:05 am
ORD
-
SDQ
2 stops9h 19m
American Airlines
Sun 9/137:34 pm
SDQ
-
ORD
1 stop13h 14m
American Airlines
Deal found 7/22$446
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:09 pm
ORD
-
SDQ
1 stop9h 37m
United Airlines
Sat 10/246:00 am
SDQ
-
ORD
1 stop9h 45m
United Airlines
Deal found 7/23$468
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:05 am
MDW
-
SDQ
1 stop6h 23m
Delta
Tue 9/152:53 pm
SDQ
-
MDW
1 stop8h 51m
Delta
Deal found 7/21$520
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am
MDW
-
SDQ
2 stops11h 24m
Delta
Wed 10/282:56 pm
SDQ
-
MDW
1 stop8h 29m
Delta
Deal found 7/23$565
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am
MDW
-
SDQ
1 stop6h 23m
Delta
Thu 8/202:53 pm
SDQ
-
MDW
1 stop8h 43m
Delta
Deal found 7/20$580

Find flight deals from Chicago to Santo Domingo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Santo Domingo (SDQ). 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 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$416
(Air Canada)

One-way from

$159
(Arajet)

Popular in

June

Cheapest in

February

Average price

$609
Provider with most accurate pricing for Chicago (CHI)-Santo Domingo Las Americas flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Santo Domingo Las Americas flights.
Search Deals
From Chicago (CHI) to Santo Domingo Las Americas
Search Deals
One-way flight from Chicago (CHI) to Santo Domingo Las Americas
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 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 Chicago to Santo Domingo 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 23, 2026.
Use the filters below to find and compare flights from Chicago to Santo Domingo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Tue 1/5

2:13 pm-11:42 am

1 stop19h 29m

Santo Domingo Las Americas

Tue 1/12

5:50 am-12:46 pm

1 stop8h 56m

$485

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Sat 10/10

6:30 am-5:55 pm

1 stop10h 25m

Santo Domingo Las Americas

Fri 10/23

9:00 am-9:56 pm

1 stop13h 56m

$534

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Thu 11/19

7:35 am-1:10 pm

1 stop27h 35m

Santo Domingo Las Americas

Thu 11/26

2:24 pm-12:11 am

1 stop11h 47m

$536

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Fri 1/15

7:00 am-12:30 am

1 stop15h 30m

Santo Domingo Las Americas

Thu 1/28

8:45 pm-10:04 am

1 stop15h 19m

$560

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Tue 11/10

9:30 am-1:35 am

2 stops14h 05m

Santo Domingo Las Americas

Tue 11/17

6:45 am-6:37 pm

2 stops13h 52m

$565

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 9/6

6:05 am-6:06 pm

2 stops11h 01m

Santo Domingo Las Americas

Tue 9/15

2:53 pm-10:44 pm

1 stop8h 51m

$585
Quickest round-trip

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 11/6

6:00 am-2:41 pm

1 stop6h 41m

Santo Domingo Las Americas

Sat 11/14

3:55 pm-10:10 pm

1 stop8h 15m

$620

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 12/9

2:50 pm-12:51 am

1 stop8h 01m

Santo Domingo Las Americas

Sun 12/13

6:01 am-4:42 pm

1 stop12h 41m

$633

ChicagoSanto Domingo

ORD - SDQ

ORDSDQ

Chicago O'Hare Intl

Wed 1/6

9:30 am-12:30 am

2 stops13h 00m

Santo Domingo Las Americas

Fri 3/5

7:30 am-8:37 pm

2 stops15h 07m

$715

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 8/12

9:24 am-12:54 am

2 stops14h 30m

Santo Domingo Las Americas

Sat 8/15

2:53 pm-10:36 pm

1 stop8h 43m

$727

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 36 resultsSorted by cheapest first
1
2
3
4

Compare providers for flights from Chicago to Santo Domingo

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 Chicago to Santo Domingo in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 Chicago-Santo Domingo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Santo Domingo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Santo Domingo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Santo Domingo 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 Chicago-Santo Domingo 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 Chicago to Santo Domingo

Have a flexible travel schedule? Discover the best time to fly to Santo Domingo from Chicago 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 Chicago to Santo Domingo

What is the cheapest month to book a flight from Chicago to Santo Domingo?

Currently, November is the cheapest month in which you can book a flight from Chicago to Santo Domingo (average of $397). Flying from Chicago to Santo Domingo in June is currently the most expensive (average of $663). 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 Chicago to Santo Domingo?

Airfare is below average for this route at the moment.
Chicago to Santo Domingo flights typically cost between $446 and $680 in January.
The cheapest round-trip price found within the last 5 days was $416 on Air Canada (Jan 17-Jan 25).

What’s the top layover airport for flights from Chicago to Santo Domingo?

Share of 1-stop round-trip flights from Chicago to Santo Domingo chosen by Cheapflights users in the past 12 months, using the same layover each way.

Miami (MIA) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago to Santo Domingo on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Santo Domingo?

Average round-trip fare for 1-stop flights from Chicago to Santo Domingo, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $387.

What’s the fastest layover option from Chicago to Santo Domingo?

Shortest average travel time for 1-stop one-way flights from Chicago to Santo Domingo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 6h 46m.

Which airport typically offers the quickest layover for flights from Chicago to Santo Domingo?

Average layover duration for 1-stop one-way flights from Chicago to Santo Domingo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Philadelphia (PHL) offer the fastest connection on this route, with an average layover time of 1h 19m.

How far ahead should I book a flight from Chicago to Santo Domingo?

The best time to book flights from Chicago to Santo Domingo is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Reviews of airlines servicing Santo Domingo

Get insights into the airlines that provide service to Santo Domingo. 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 Santo Domingo. Reviews last updated July 23, 2026.
Read reviews from past customers who have flown Delta,American Airlines, andJetBlue from Chicago to Santo Domingo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,484 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,484 reviews
Delta
7.8
Good
8,484 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,838 reviews
Delta
7.8
Good
8,484 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
JetBlue
7.1
Good
3,021 reviews
Delta
7.8
Good
8,484 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

Related info for your journey

Find useful and relevant information for your journey from Chicago to Santo Domingo. 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 into for flights to Santo Domingo from Chicago?

    Most people fly into Santo Domingo Las Americas (SDQ) if they book a flight to Santo Domingo from Chicago. On average, Las Americas has 0 inbound flights from Chicago per day from 4 airlines. Santo Domingo Las Americas is conveniently located just 17.5 mi from Santo Domingo’s city center.

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

    There are many flights that can get you from Chicago to Santo Domingo in 6h 23m. Fly via Copa Airlines or Delta to get the fastest option. The distance between Chicago and Santo Domingo is about 1932 mi. This flight may include one or multiple stops.

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

    Currently priced at $261, Delta will fly you from Chicago to Santo Domingo and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from JetBlue and American Airlines - these airlines can fly you to your destination from $354 and $383, respectively. Delta is priced at 50% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Santo Domingo 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 Chicago to Santo Domingo?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Santo Domingo (average of $397). Flying from Chicago to Santo Domingo in June is currently the most expensive (average of $663). 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 Santo Domingo?

Book flights to Santo Domingo if you plan to visit one of these locations
Juan Dolio

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Chicago to Santo Domingo

Discover the top 4 airlines that operate flights from Chicago to Santo Domingo. 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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$546FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$354Average$457FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$383Average$535FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$402Average$557FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.