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$215+ Cheap flights from Santo Domingo (SDQ) to Midway (MDW)

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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Santo Domingo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Santo Domingo (SDQ) to Midway (MDW). 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$438
(Delta)

One-way from

$229
(Trip.com)

Popular in

August

Cheapest in

September

Average price

$515
Provider with most accurate pricing for Santo Domingo Las Americas-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Santo Domingo Las Americas-Chicago Midway flights.
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From Santo Domingo Las Americas to Chicago Midway
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One-way flight from Santo Domingo Las Americas to Chicago Midway
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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Santo Domingo to Midway

Cheapest flights from Santo Domingo to Midway
Explore the most affordable flight options available from Santo Domingo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/87:00 amSDQ - MDW
2 stops15h 28mDelta
Mon 5/129:16 amMDW - SDQ
2 stops14h 03mDelta
Deal found 4/29$438
This Frontier deal was found by Cheapflights users on 4/29. 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 6/510:23 amSDQ - MDW
1 stop10h 54mFrontier
Sat 6/146:20 amMDW - SDQ
2 stops10h 06mFrontier
Deal found 4/29$454
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Mon 5/51:25 amSDQ - MDW
3 stops16h 54mMultiple Airlines
Sun 5/119:20 amMDW - SDQ
3 stops24h 30mMultiple Airlines
Deal found 4/29$1,458

Cheapflights Fare Finder

Customize your flight search to find flights from Santo Domingo to Midway 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 May 1, 2025.
Use the filters below to find and compare flights from Santo Domingo to Chicago Midway Airport that are best for you.

Fly from

Santo Domingo

Fly to

Midway

Route

Depart

Return

Price

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

$438

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 6/5

10:23 am-8:17 pm

1 stop10h 54m

Chicago Midway

Sat 6/14

6:20 am-5:26 pm

2 stops10h 06m

$454

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 6/26

7:15 am-8:17 pm

1 stop14h 02m

$215

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 6/15

11:49 am-8:17 pm

1 stop9h 28m

$229

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 6/10

6:00 am-6:41 pm

2 stops13h 41m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from Santo Domingo to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Santo Domingo to Midway in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Santo Domingo-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Santo Domingo-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Santo Domingo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Santo Domingo-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Santo Domingo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Santo Domingo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport 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 Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Santo Domingo to Midway. 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 Midway?

    For a flight from Santo Domingo to Chicago Midway, you will be flying from Las Americas. Santo Domingo Las Americas (SDQ) is just 17.5 mi from the center of the city. Las Americas is the only Santo Domingo airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Santo Domingo Las Americas on a regular basis.

  • What are the cheapest airlines flying from Santo Domingo to Chicago Midway Airport round-trip?

    According to our current data, Delta ($438), and Frontier ($473) offers the cheapest pricing from Santo Domingo to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Santo Domingo to Midway 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 Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Santo Domingo to Chicago Midway Airport (average of $160). Flying from Santo Domingo to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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