$175 Cheap Flights from Chicago (MDW) to Santo Domingo (SDQ)

View $175 flight on Tue, Aug 12, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Las Americas Intl. Airport (SDQ)

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Cheap Flights from Chicago to Santo Domingo (MDW-SDQ)

Prices were available within the past 7 days and start at $175 for one-way flights and $392 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Aug 9 - Thu, Aug 14
MDW
Chicago
SDQ
Santo Domingo
$392 Roundtrip, found 5 days ago
$392
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 9 from Chicago to Santo Domingo, returning Thu, Aug 14, priced at $392 found 5 days ago
Frontier Airlines
Tue, Aug 12 - Thu, Aug 14
MDW
Chicago
SDQ
Santo Domingo
$393 Roundtrip, found 1 day ago
$393
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 12 from Chicago to Santo Domingo, returning Thu, Aug 14, priced at $393 found 1 day ago
Frontier Airlines
Wed, Oct 22 - Sun, Oct 26
MDW
Chicago
SDQ
Santo Domingo
$400 Roundtrip, found 10 hours ago
$400
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Oct 22 from Chicago to Santo Domingo, returning Sun, Oct 26, priced at $400 found 10 hours ago
Frontier Airlines
Tue, Aug 12 - Sun, Aug 17
MDW
Chicago
SDQ
Santo Domingo
$402 Roundtrip, found 7 hours ago
$402
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Aug 12 from Chicago to Santo Domingo, returning Sun, Aug 17, priced at $402 found 7 hours ago
Frontier Airlines
Mon, Aug 11 - Thu, Aug 14
MDW
Chicago
SDQ
Santo Domingo
$413 Roundtrip, found 8 hours ago
$413
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Chicago to Santo Domingo, returning Thu, Aug 14, priced at $413 found 8 hours ago
Frontier Airlines
Mon, Aug 11 - Fri, Aug 15
MDW
Chicago
SDQ
Santo Domingo
$421 Roundtrip, found 6 hours ago
$421
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Chicago to Santo Domingo, returning Fri, Aug 15, priced at $421 found 6 hours ago
Frontier Airlines
Fri, Dec 12 - Sun, Dec 14
MDW
Chicago
SDQ
Santo Domingo
$422 Roundtrip, found 6 days ago
$422
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Chicago to Santo Domingo, returning Sun, Dec 14, priced at $422 found 6 days ago
Delta
Sat, Sep 6 - Wed, Sep 24
MDW
Chicago
SDQ
Santo Domingo
$427 Roundtrip, found 1 hour ago
$427
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Sep 6 from Chicago to Santo Domingo, returning Wed, Sep 24, priced at $427 found 1 hour ago
Frontier Airlines
Thu, Aug 7 - Mon, Aug 11
MDW
Chicago
SDQ
Santo Domingo
$431 Roundtrip, found 2 days ago
$431
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 7 from Chicago to Santo Domingo, returning Mon, Aug 11, priced at $431 found 2 days ago
Delta
Sat, Jan 31 - Wed, Feb 4
MDW
Chicago
SDQ
Santo Domingo
$431 Roundtrip, found 2 days ago
$431
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jan 31 from Chicago to Santo Domingo, returning Wed, Feb 4, priced at $431 found 2 days ago

Find the cheapest month to fly from Chicago (MDW) to Santo Domingo (SDQ)

October is typically the cheapest month to fly

From $334 - $1,056 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Santo Domingo (SDQ)
Origin airport
Midway Intl.
Destination airport
Las Americas Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$391
Distance
1932 mi

Chicago to Santo Domingo Flights

The cheapest times to fly from Chicago to Santo Domingo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Santo Domingo are during the month of August. You can find some of the cheapest flights from Chicago to Santo Domingo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Santo Domingo

Sunday is one of the best days to book for cheap flights from Chicago to Santo Domingo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Santo Domingo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Santo Domingo in 2025. You can also book with separate airlines for your outbound and return journeys, from $175 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Santo Domingo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Santo Domingo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ) cost?
Discover the latest flight deals from MDW to SDQ by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to SDQ?
The cheapest flights from MDW to SDQ are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to SDQ?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to SDQ. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ)?
You'll need to hop on a flight with a layover when traveling from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to SDQ?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can vary based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ)?
Choose a flight from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ) last-minute?
Waiting until right before your break to book a flight from MDW to SDQ often results in higher prices. While you might find some last-minute offers, there's no guarantee. Keep your travel schedule open for a better chance of getting a bargain.
Is it cheaper to book a MDW to SDQ flight and hotel package?
Booking a MDW to SDQ flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Pick from our extensive range of stays and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ)?
If you reserved your MDW to SDQ flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

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*Available to One Key members.