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$186+ 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Santo Domingo Las Americas to Chicago are usually found in September or July, 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 June 12, 2025.

Round-trip from

$351
(Cheapflightsfares)

One-way from

$186
(Kiwi.com)

Popular in

August

Cheapest in

September

Average price

$548
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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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
Sun 9/77:30 amSDQ - ORD
1 stop7h 45mSpirit Airlines
Tue 9/161:03 pmORD - SDQ
1 stop12h 07mSpirit Airlines
Deal found 6/12$351
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:11 pmSDQ - ORD
1 stop9h 59mFrontier
Sun 10/195:10 amORD - SDQ
1 stop7h 41mFrontier
Deal found 6/12$387
This Frontier deal was found by Cheapflights users on 6/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:11 pmSDQ - MDW
1 stop9h 14mFrontier
Sun 10/196:15 amMDW - SDQ
1 stop6h 36mFrontier
Deal found 6/12$387
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/87:15 amSDQ - ORD
1 stop14h 08mMultiple Airlines
Thu 7/177:05 amORD - SDQ
1 stop25h 04mMultiple Airlines
Deal found 6/10$400
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 10/273:15 pmSDQ - ORD
1 stop9h 38mDelta
Thu 10/307:00 amORD - SDQ
2 stops9h 52mDelta
Deal found 6/11$450
This Delta deal was found by Cheapflights users on 6/9. 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 10/273:15 pmSDQ - MDW
1 stop7h 29mDelta
Thu 10/309:30 amMDW - SDQ
2 stops12h 59mDelta
Deal found 6/9$450
This Copa Airlines deal was found by Cheapflights users on 6/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/302:07 pmSDQ - ORD
1 stop11h 13mCopa Airlines
Mon 8/43:07 pmORD - SDQ
1 stop10h 38mCopa Airlines
Deal found 6/10$457
This American Airlines deal was found by Cheapflights users on 6/9. 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 7/257:20 pmSDQ - ORD
1 stop14h 42mAmerican Airlines
Fri 8/14:49 pmORD - SDQ
1 stop15h 26mAmerican Airlines
Deal found 6/9$469
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/262:45 amSDQ - ORD
1 stop13h 23mJetBlue
Thu 10/304:05 pmORD - SDQ
1 stop7h 19mJetBlue
Deal found 6/11$554
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1010:55 amSDQ - MDW
2 stops23h 46mMultiple Airlines
Mon 7/1410:31 amMDW - SDQ
2 stops22h 19mMultiple Airlines
Deal found 6/10$557
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/273:18 pmSDQ - ORD
1 stop9h 16mUnited Airlines
Thu 10/301:36 pmORD - SDQ
1 stop8h 10mUnited Airlines
Deal found 6/10$566

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 12, 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

Sun 9/7

7:30 am-2:15 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 9/16

1:03 pm-2:10 am

1 stop12h 07m

$351

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Thu 10/9

3:11 pm-12:10 am

1 stop9h 59m

Chicago O'Hare Intl

Sun 10/19

5:10 am-1:51 pm

1 stop7h 41m

$387

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Sun 10/19

6:15 am-1:51 pm

1 stop6h 36m

$387

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Tue 7/8

7:15 am-8:23 pm

1 stop14h 08m

Chicago O'Hare Intl

Thu 7/17

7:05 am-9:09 am

1 stop25h 04m

$400

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Mon 10/27

3:15 pm-11:53 pm

1 stop9h 38m

Chicago O'Hare Intl

Thu 10/30

7:00 am-5:52 pm

2 stops9h 52m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

7:00 am-6:36 pm

2 stops12h 36m

Chicago Midway

Thu 10/30

9:30 am-11:29 pm

2 stops12h 59m

$450

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Wed 7/30

2:07 pm-12:20 am

1 stop11h 13m

Chicago O'Hare Intl

Mon 8/4

3:07 pm-2:45 am

1 stop10h 38m

$457

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Fri 7/25

7:20 pm-9:02 am

1 stop14h 42m

Chicago O'Hare Intl

Fri 8/1

4:49 pm-9:15 am

1 stop15h 26m

$469

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

Sun 10/26

2:45 am-3:08 pm

1 stop13h 23m

Chicago O'Hare Intl

Thu 10/30

4:05 pm-12:24 am

1 stop7h 19m

$554

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 7/10

10:55 am-9:41 am

2 stops23h 46m

Chicago Midway

Mon 7/14

10:31 am-9:50 am

2 stops22h 19m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 20 results
1
2

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 June 9, 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 June 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 12, 2025.
To help decide which airline to fly from Santo Domingo to Chicago, see what other customers have to say about Delta, Copa Airlines and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,451 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,925 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $351 on this airline. Additional options worth looking into are Frontier and Delta, starting at $387 and $450 round-trip. Spirit Airlines is currently priced 29% below the average price you’ll pay for this route.

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

    $186 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 Frontier and Delta, with prices starting from $200 and $242, 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 $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 Santo Domingo?

Book flights to Santo Domingo if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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.
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Santo Domingo to O'Hare Intl 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$324Average$507FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$440Average$523FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$447Average$627FlexibilityNo cancel feeOn-time71%

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