What is the cheapest airline to fly from Chicago Midway Airport to Santo Domingo round-trip?

Flying on Delta is currently your cheapest option to Santo Domingo, with prices starting at $375. Delta is 38% cheaper than the average price of flights available within the next 90 days to this destination.

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Santo Domingo (average of $362). Flying from Chicago Midway Airport to Santo Domingo in December is currently the most expensive (average of $583). 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 day to fly from Chicago Midway Airport to Santo Domingo?

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

In terms of precipitation, rainfall in Santo Domingo ranges from 1.6 - 6.7 inches per month. May is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Santo Domingo when rainfall is around 1.6 in.

If weather is an important factor for your trip to Santo Domingo, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 75.2 F).

What is the cheapest day to fly round-trip from Chicago Midway Airport to Santo Domingo?

Users have found that flying from Chicago Midway Airport to Santo Domingo on a Wednesday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

How far in advance should I book a flight from Chicago Midway Airport to Santo Domingo?

Travelers have found it’s best to book a flight 48 days in advance to save up to 38% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 48 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Santo Domingo 1-2 weeks in advance for as low as $357, or $454 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to Santo Domingo?

Our data shows that August tends to be the cheapest month to fly to Santo Domingo from Chicago Midway Airport. Users have commonly found prices around $516 for the month, but tickets can be as low as $320. Due to multiple factors, prepare for potentially higher prices in December.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Santo Domingo as you normally would.

What airport do you fly into for flights to Santo Domingo from Chicago Midway?

Located just 17.5 mi from the city center, Santo Domingo Las Americas is the airport most travelers will use when flying to Santo Domingo from Chicago Midway. Booking flights from Chicago Midway to Las Americas (SDQ) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

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

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

How can I find direct flights from Midway to Santo Domingo?

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

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

Yes. Cheapflights offers flight deals from Midway 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.

$193+ Flights from Chicago Midway Airport to Santo Domingo

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Cheap flight deals from Midway to Santo Domingo

Round-trip from	$403 (Kiwi.com)
One-way from	$193 (Kiwi.com)
Popular in	August
Cheapest in	March
Average price	$1,189

From Chicago Midway to Santo Domingo Las Americas

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One-way flight from Chicago Midway to Santo Domingo Las Americas

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Highest demand for flights based on searches. 12% potential increase in price ($87 potential increase over avg. RT price).

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Cheapest flight prices on average. 10% potential price decrease ($58 potential savings vs. average RT price).

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Average for round-trip flights in August 2025

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Find flight deals from Midway to Santo Domingo

Cheapest flights from Midway to Santo Domingo
Explore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

Sat 9/2010:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Sat 9/272:12 pmSDQ - MDW

1 stop20h 06mMultiple Airlines

Deal found 8/13

$405

Sat 9/1310:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Mon 9/2210:19 amSDQ - MDW

2 stops14h 01mMultiple Airlines

Deal found 8/14

$418

Thu 9/119:35 amMDW - SDQ

2 stops14h 01mDelta

Sat 9/203:06 pmSDQ - MDW

1 stop7h 04mDelta

Deal found 8/12

$419

Sat 9/131:08 pmMDW - SDQ

2 stops10h 28mDelta

Sat 9/203:06 pmSDQ - MDW

1 stop7h 04mDelta

Deal found 8/14

$431

Sat 11/811:10 amMDW - SDQ

2 stops12h 17mDelta

Wed 11/124:22 pmSDQ - MDW

1 stop7h 22mDelta

Deal found 8/14

$434

Sun 11/96:20 amMDW - SDQ

1 stop6h 36mFrontier

Thu 11/134:19 pmSDQ - MDW

1 stop7h 44mFrontier

Deal found 8/14

$436

Thu 9/2512:43 pmMDW - SDQ

2 stops10h 53mDelta

Mon 9/292:50 pmSDQ - MDW

1 stop7h 46mDelta

Deal found 8/12

$474

Sat 10/186:00 amMDW - SDQ

1 stop6h 41mDelta

Sat 10/252:56 pmSDQ - MDW

1 stop8h 18mDelta

Deal found 8/14

$513

Best flights from Midway to Santo Domingo
Discover carefully curated flight deals from Midway to Santo Domingo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Sat 9/2010:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Sat 9/272:12 pmSDQ - MDW

1 stop20h 06mMultiple Airlines

Deal found 8/13

$405

Thu 9/119:35 amMDW - SDQ

2 stops14h 01mDelta

Sat 9/203:06 pmSDQ - MDW

1 stop7h 04mDelta

Deal found 8/12

$419

Sat 9/1310:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Mon 9/2210:19 amSDQ - MDW

2 stops14h 01mMultiple Airlines

Deal found 8/14

$418

Thu 10/239:35 amMDW - SDQ

2 stops13h 52mDelta

Tue 10/286:05 amSDQ - MDW

2 stops13h 20mDelta

Deal found 8/12

$431

Sat 9/610:31 amMDW - SDQ

2 stops13h 27mDelta

Sat 9/136:03 amSDQ - MDW

2 stops13h 32mDelta

Deal found 8/13

$431

Sat 9/139:35 amMDW - SDQ

2 stops14h 01mDelta

Sat 9/206:03 amSDQ - MDW

2 stops13h 32mDelta

Deal found 8/12

$431

Last-minute flights from Midway to Santo Domingo
Discover last-minute flight deals from Midway to Santo Domingo. Data last updated August 14, 2025 and is based on user searches.

Wed 8/206:04 amMDW - SDQ

1 stop6h 18mDelta

Mon 8/252:47 pmSDQ - MDW

1 stop7h 57mDelta

Deal found 8/14

$660

Wed 8/208:39 pmMDW - SDQ

3 stops22h 51mMultiple Airlines

Mon 8/2511:45 amSDQ - MDW

3 stops29h 39mMultiple Airlines

Deal found 8/14

$2,883

Thu 8/216:04 amMDW - SDQ

1 stop6h 18mDelta

Sun 8/242:47 pmSDQ - MDW

1 stop7h 57mDelta

Deal found 8/12

$763

Fri 8/226:04 amMDW - SDQ

1 stop6h 18mDelta

Sun 8/242:47 pmSDQ - MDW

1 stop7h 57mDelta

Deal found 8/12

$905

Thu 9/46:00 amMDW - SDQ

1 stop6h 22mDelta

Mon 9/82:47 pmSDQ - MDW

1 stop7h 39mDelta

Deal found 8/12

$513

Sat 9/66:00 amMDW - SDQ

1 stop6h 38mDelta

Sat 9/136:03 amSDQ - MDW

2 stops13h 32mDelta

Deal found 8/14

$517

Thu 9/119:35 amMDW - SDQ

2 stops14h 01mDelta

Sat 9/203:06 pmSDQ - MDW

1 stop7h 04mDelta

Deal found 8/12

$419

Thu 9/119:35 amMDW - SDQ

2 stops14h 01mDelta

Tue 9/162:50 pmSDQ - MDW

1 stop7h 46mDelta

Deal found 8/14

$560

Sat 9/1310:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Mon 9/2210:19 amSDQ - MDW

2 stops14h 01mMultiple Airlines

Deal found 8/14

$418

Sat 9/131:08 pmMDW - SDQ

2 stops10h 28mDelta

Sat 9/203:06 pmSDQ - MDW

1 stop7h 04mDelta

Deal found 8/14

$431

Sat 9/2010:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Sat 9/272:12 pmSDQ - MDW

1 stop20h 06mMultiple Airlines

Deal found 8/13

$405

Thu 9/2512:43 pmMDW - SDQ

2 stops10h 53mDelta

Mon 9/292:50 pmSDQ - MDW

1 stop7h 46mDelta

Deal found 8/12

$474

One-way flights from Midway to Santo Domingo
Search for one-way flight options from Midway to Santo Domingo. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Sat 9/1310:51 amMDW - SDQ

1 stop24h 24mMultiple Airlines

Deal found 8/14

$193

Mon 9/89:47 pmMDW - SDQ

2 stops17h 13mMultiple Airlines

Deal found 8/13

$200

Mon 9/86:00 amMDW - SDQ

1 stop6h 22mDelta

Deal found 8/13

$202

Wed 8/2012:43 pmMDW - SDQ

2 stops11h 09mDelta

Deal found 8/13

$207

Tue 9/92:32 pmMDW - SDQ

2 stops24h 28mMultiple Airlines

Deal found 8/14

$210

Thu 8/2811:03 amMDW - SDQ

2 stops23h 53mMultiple Airlines

Deal found 8/13

$225

Thu 10/24:56 pmMDW - SDQ

2 stops22h 33mMultiple Airlines

Deal found 8/12

$244

Wed 10/16:00 amMDW - SDQ

1 stop6h 24mDelta

Deal found 8/13

$245

Thu 9/119:35 amMDW - SDQ

2 stops14h 01mDelta

Deal found 8/13

$251

Wed 8/208:00 amMDW - SDQ

3 stops31h 00mMultiple Airlines

Deal found 8/13

$256

Sun 8/246:04 amMDW - SDQ

1 stop6h 18mDelta

Deal found 8/13

$288

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Santo Domingo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/20

10:51 am-12:15 pm

1 stop24h 24m

Santo Domingo Las Americas

Sat 9/27

2:12 pm-9:18 am

1 stop20h 06m

$405

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/13

10:51 am-12:15 pm

1 stop24h 24m

Santo Domingo Las Americas

Mon 9/22

10:19 am-11:20 pm

2 stops14h 01m

$418

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 9/11

9:35 am-12:36 am

2 stops14h 01m

Santo Domingo Las Americas

Sat 9/20

3:06 pm-9:10 pm

1 stop7h 04m

$419

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 10/23

9:35 am-12:27 am

2 stops13h 52m

Santo Domingo Las Americas

Tue 10/28

6:05 am-6:25 pm

2 stops13h 20m

$431

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/6

10:31 am-12:58 am

2 stops13h 27m

Santo Domingo Las Americas

Sat 9/13

6:03 am-6:35 pm

2 stops13h 32m

$431

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/13

9:35 am-12:36 am

2 stops14h 01m

Santo Domingo Las Americas

Sat 9/20

6:03 am-6:35 pm

2 stops13h 32m

$431

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/13

10:51 am-12:15 pm

1 stop24h 24m

$193

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 9/8

9:47 pm-4:00 pm

2 stops17h 13m

$200

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 9/13

11:00 am-12:36 am

2 stops12h 36m

$202

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 9/8

6:00 am-1:22 pm

1 stop6h 22m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 13 results

Best time to book a flight from Midway to Santo Domingo

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

Reviews of airlines servicing Santo Domingo

Read reviews from past customers who have flown Delta from Chicago Midway Airport 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

8.0

Very good

7,980 reviews

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

7,980 reviews

Delta

8.0

Very good

7,980 reviews

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

What airport do you fly into for flights to Santo Domingo from Chicago Midway?
Located just 17.5 mi from the city center, Santo Domingo Las Americas is the airport most travelers will use when flying to Santo Domingo from Chicago Midway. Booking flights from Chicago Midway to Las Americas (SDQ) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.
What is the cheapest airline to fly from Chicago Midway Airport to Santo Domingo round-trip?
Flying on Delta is currently your cheapest option to Santo Domingo, with prices starting at $375. Delta is 38% cheaper than the average price of flights available within the next 90 days to this destination.
Can I find deals for flights from Midway to Santo Domingo that include hotel bookings?
Yes. In addition to deals on Midway to Santo Domingo flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to Santo Domingo?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Santo Domingo.
Can I find deals for business class flights from Midway to Santo Domingo?
Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to Santo Domingo?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Santo Domingo (average of $362). Flying from Chicago Midway Airport to Santo Domingo in December is currently the most expensive (average of $583). 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

Juan Dolio

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Midway to Santo Domingo

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$375	Average$604	FlexibilityNo cancel fee	On-timeN/A

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$193+ Cheap flights from Midway (MDW) 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Santo Domingo with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Santo Domingo

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to Santo Domingo

Cheapest flights from Midway to Santo DomingoExplore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

Explore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Santo Domingo that are best for you.

Best time to book a flight from Midway to Santo Domingo

Have a flexible travel schedule? Discover the best time to fly to Santo Domingo from Midway with our price prediction graph.

Reviews of airlines servicing Santo Domingo

Read reviews from past customers who have flown Delta from Chicago Midway Airport 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.

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Midway?

What is the cheapest airline to fly from Chicago Midway Airport to Santo Domingo round-trip?

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

How can I find direct flights from Midway to Santo Domingo?

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

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

Traveling to a place near Santo Domingo?

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Alternative routes for Midway to Santo Domingo

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to Santo Domingo

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Cheapest flights from Midway to Santo Domingo
Explore the most affordable flight options available from Midway to Santo Domingo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.