$176 Cheap Flights from Chicago (MDW) to Santo Domingo (SDQ)

View $176 flight on Tue, Oct 21, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $176 for one-way flights and $375 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Oct 26 - Wed, Oct 29
MDW
Chicago
SDQ
Santo Domingo
$375 Roundtrip, found 1 hour ago
$375
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Oct 26 from Chicago to Santo Domingo, returning Wed, Oct 29, priced at $375 found 1 hour ago
Delta
Mon, Oct 27 - Wed, Nov 5
MDW
Chicago
SDQ
Santo Domingo
$376 Roundtrip, found 1 day ago
$376
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Santo Domingo, returning Wed, Nov 5, priced at $376 found 1 day ago
Frontier Airlines
Wed, Oct 29 - Sun, Nov 2
MDW
Chicago
SDQ
Santo Domingo
$377 Roundtrip, found 3 days ago
$377
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Oct 29 from Chicago to Santo Domingo, returning Sun, Nov 2, priced at $377 found 3 days ago
Delta
Sun, Nov 2 - Wed, Nov 12
MDW
Chicago
SDQ
Santo Domingo
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Nov 2 from Chicago to Santo Domingo, returning Wed, Nov 12, priced at $377 found 1 day ago
Frontier Airlines
Fri, Dec 5 - Sun, Dec 7
MDW
Chicago
SDQ
Santo Domingo
$379 Roundtrip, found 3 days ago
$379
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Chicago to Santo Domingo, returning Sun, Dec 7, priced at $379 found 3 days ago
Frontier Airlines
Wed, Oct 15 - Sun, Oct 19
MDW
Chicago
SDQ
Santo Domingo
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Oct 15 from Chicago to Santo Domingo, returning Sun, Oct 19, priced at $381 found 4 days ago
Delta
Tue, Nov 18 - Thu, Dec 4
MDW
Chicago
SDQ
Santo Domingo
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Nov 18 from Chicago to Santo Domingo, returning Thu, Dec 4, priced at $381 found 4 days ago
Delta
Sun, Oct 26 - Wed, Nov 5
MDW
Chicago
SDQ
Santo Domingo
$382 Roundtrip, found 4 days ago
$382
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Oct 26 from Chicago to Santo Domingo, returning Wed, Nov 5, priced at $382 found 4 days ago
Delta
Mon, Oct 20 - Wed, Oct 29
MDW
Chicago
SDQ
Santo Domingo
$385 Roundtrip, found 4 days ago
$385
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 20 from Chicago to Santo Domingo, returning Wed, Oct 29, priced at $385 found 4 days ago
Delta
Sat, Oct 25 - Wed, Nov 5
MDW
Chicago
SDQ
Santo Domingo
$387 Roundtrip, found 4 days ago
$387
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 25 from Chicago to Santo Domingo, returning Wed, Nov 5, priced at $387 found 4 days ago

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

June is typically the cheapest month to fly

From $365 - $1,070 per traveler.

Alternative airports near Santo Domingo

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Las Americas Intl. SDQ. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $435
SDQ
Las Americas Intl.
Cheapest
Average driving time to city center22 min
Flights from $435

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ) cost?
Get a cheap one-way flight from $176 or cheap return flight from $375 from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ)?
Planning your getaway for October is a great way to save, as it's the cheapest month for flights between MDW and SDQ. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Las Americas Intl. Airport (SDQ)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest MDW to SDQ flight.
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.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Las Americas Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$374
Distance
1932 mi

Book with confidence

Book with confidence

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 October. 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 $176 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.

 

Chicago to Santo Domingo Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.