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$165+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Santo Domingo Las Americas to Chicago are usually found in November or September, booked 36 days in advance, depart on a Monday or Sunday and return on a Tuesday

Cheap 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 September 11, 2025.

Round-trip from

$264
(Priceline)

One-way from

$165
(Cheapflightsfares)

Popular in

August

Cheapest in

November

Average price

$454
From Santo Domingo Las Americas to Chicago (CHI)
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One-way flight from Santo Domingo Las Americas to Chicago (CHI)
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Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/11. 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.
Sat 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Thu 10/235:05 amORD - SDQ
1 stop8h 43mSpirit Airlines
Deal found 9/11$264
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/43:47 pmSDQ - ORD
1 stop8h 01mSpirit Airlines
Sat 10/115:05 amORD - SDQ
1 stop8h 49mSpirit Airlines
Deal found 9/11$273
This Spirit deal was found by Cheapflights users on 9/11. 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.
Sat 10/113:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Sat 10/255:05 amORD - SDQ
1 stop8h 49mSpirit Airlines
Deal found 9/11$276
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/303:54 pmSDQ - ORD
1 stop10h 09mSpirit Airlines
Wed 11/55:05 amORD - SDQ
1 stop10h 45mSpirit Airlines
Deal found 9/11$290
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 10/253:59 pmSDQ - ORD
1 stop8h 46mSpirit Airlines
Fri 10/315:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/11$292
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/303:54 pmSDQ - ORD
1 stop10h 09mSpirit Airlines
Mon 11/35:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/10$298
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 10/105:12 pmSDQ - ORD
1 stop7h 33mSpirit Airlines
Mon 10/135:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/10$299
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/35:05 pmSDQ - ORD
1 stop18h 47mSpirit Airlines
Sat 10/117:43 pmORD - SDQ
1 stop18h 05mSpirit Airlines
Deal found 9/11$303
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:12 pmSDQ - ORD
1 stop8h 51mSpirit Airlines
Mon 11/35:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/11$306
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/35:05 pmSDQ - ORD
1 stop18h 47mSpirit Airlines
Mon 10/65:05 amORD - SDQ
1 stop10h 02mSpirit Airlines
Deal found 9/11$308
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2912:56 pmSDQ - MDW
2 stops26h 37mMultiple Airlines
Tue 11/46:26 pmMDW - SDQ
1 stop20h 00mMultiple Airlines
Deal found 9/10$386
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/116:05 amSDQ - MDW
2 stops13h 20mDelta
Sat 10/2511:10 amMDW - SDQ
2 stops12h 17mDelta
Deal found 9/11$388

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 September 11, 2025.
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

Sat 10/11

3:59 pm-11:45 pm

1 stop8h 46m

Chicago O'Hare Intl

Sat 10/25

5:05 am-2:54 pm

1 stop8h 49m

$276

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 10/10

5:12 pm-11:45 pm

1 stop7h 33m

Chicago O'Hare Intl

Mon 10/13

5:05 am-4:07 pm

1 stop10h 02m

$299

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 10/3

5:05 pm-10:52 am

1 stop18h 47m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-2:48 pm

1 stop18h 05m

$303

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 10/27

5:12 pm-1:03 am

1 stop8h 51m

Chicago O'Hare Intl

Mon 11/3

5:05 am-5:07 pm

1 stop10h 02m

$306

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 11/13

6:55 pm-9:23 am

1 stop16h 28m

Chicago O'Hare Intl

Wed 11/19

5:05 am-5:50 pm

1 stop10h 45m

$312

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 10/16

3:54 pm-11:45 pm

1 stop8h 51m

Chicago O'Hare Intl

Wed 10/22

7:43 pm-2:48 pm

1 stop18h 05m

$317

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 10/9

3:54 pm-11:45 pm

1 stop8h 51m

Chicago O'Hare Intl

Mon 10/13

5:05 am-4:07 pm

1 stop10h 02m

$318

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 10/5

3:54 pm-10:31 am

2 stops19h 37m

Chicago O'Hare Intl

Sat 10/11

7:43 pm-2:48 pm

1 stop18h 05m

$349

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 10/29

12:56 pm-2:33 pm

2 stops26h 37m

Chicago Midway

Tue 11/4

6:26 pm-4:26 pm

1 stop20h 00m

$386

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 10/11

6:05 am-6:25 pm

2 stops13h 20m

Chicago Midway

Sat 10/25

11:10 am-12:27 am

2 stops12h 17m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 34 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Santo Domingo to Chicago. Price data was last updated on August 29, 2025.

The best time to book flights from Santo Domingo to Chicago is 20 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.

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 $245). Flying from Santo Domingo to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from SDQ to CHI?

Find hourly flight availability from Santo Domingo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

A simple way to save on the total cost of your ticket is to fly from Santo Domingo to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Santo Domingo to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Santo Domingo to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Santo Domingo to Chicago flight should consider departing on Monday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 2025.
Peruse reviews from past customers who have flown with Delta and 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.
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 46m. 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. Additional options worth looking into are Delta and American Airlines, starting at $400 and $468 round-trip. Spirit Airlines is currently priced 62% below the average price you’ll pay for this route.

  • 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 $245). Flying from Santo Domingo to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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
Santo Domingo to Midway flights
Punta Cana to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Punta Cana to Midway flights

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$189Average$330FlexibilityNo cancel feeOn-time65%
DeltaCheapest$400Average$507FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$570FlexibilityNo cancel feeOn-time71%

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