HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$209+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SDQ — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Santo Domingo to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 29, 2025.

Round-trip from

$423
(Mytrip)

One-way from

$209
(Frontier)

Popular in

August

Cheapest in

September

Average price

$487
From Santo Domingo Las Americas to Chicago Midway
Search Deals
One-way flight from Santo Domingo Las Americas to Chicago Midway
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/28. 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.
Sun 8/31:48 amSDQ - MDW
1 stop22h 29mFrontier
Mon 8/116:40 pmMDW - SDQ
1 stop16h 09mFrontier
Deal found 7/28$423
This Delta deal was found by Cheapflights users on 7/28. 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 10/272:56 pmSDQ - MDW
1 stop8h 18mDelta
Thu 10/306:00 amMDW - SDQ
1 stop6h 41mDelta
Deal found 7/28$450
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/31:48 amSDQ - MDW
1 stop22h 29mMultiple Airlines
Mon 8/116:20 amMDW - SDQ
2 stops8h 27mMultiple Airlines
Deal found 7/28$612

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 July 29, 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

Sun 8/3

1:48 am-11:17 pm

1 stop22h 29m

Chicago Midway

Mon 8/11

6:40 pm-11:49 am

1 stop16h 09m

$423

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Thu 10/30

6:00 am-1:41 pm

1 stop6h 41m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sun 8/3

1:48 am-11:17 pm

1 stop22h 29m

Chicago Midway

Mon 8/11

6:20 am-3:47 pm

2 stops8h 27m

$612

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 8/5

1:48 am-10:40 am

1 stop9h 52m

$209

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 8/21

5:05 pm-8:22 am

2 stops16h 17m

$237

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 10/8

2:56 pm-10:14 pm

1 stop8h 18m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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.

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 July 29, 2025.
Peruse reviews from past customers who have flown with Delta and Frontier from Santo Domingo to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Frontier
5.9
Fair
3,238 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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, Frontier ($423), and Delta ($450) 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Santo Domingo to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Santiago de los Caballeros to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.