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Cheap flights from Chicago Midway Airport to Santo Domingo from $196

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Santo Domingo departing on 12/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Santo Domingo

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:59 pm - 9:45 pmMDW-SDQ
28h 46m1 stop
Multiple Airlines Logo
3:35 pm - 10:30 pmSDQ-MDW
8h 55m1 stop
$323Multiple Airlines
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Sat, Dec 6 - Sat, Dec 13
Multiple Airlines Logo
2:16 pm - 11:20 amMDW-SDQ
19h 04m1 stop
Multiple Airlines Logo
10:19 am - 2:47 pmSDQ-MDW
30h 28m1 stop
$372Multiple Airlines
Find Deal
Sun, Jan 4 - Wed, Jan 14
Multiple Airlines Logo
2:16 pm - 11:20 amMDW-SDQ
19h 04m1 stop
Multiple Airlines Logo
10:19 am - 9:31 pmSDQ-MDW
13h 12m2 stops
$401Multiple Airlines
Find Deal
Sun, Jan 4 - Wed, Jan 14
Delta Logo
9:34 am - 12:32 amMDW-SDQ
12h 58m2 stops
Delta Logo
7:31 am - 10:26 pmSDQ-MDW
16h 55m2 stops
$434Delta
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Sun, Jan 25 - Tue, Jan 27
Delta Logo
9:29 am - 1:48 amMDW-SDQ
14h 19m2 stops
Delta Logo
3:57 pm - 11:47 pmSDQ-MDW
9h 50m1 stop
$473Delta
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Sat, Dec 6 - Sun, Dec 14
Delta Logo
6:00 am - 2:21 pmMDW-SDQ
6h 21m1 stop
Delta Logo
3:46 pm - 10:26 pmSDQ-MDW
8h 40m1 stop
$474Delta
Find Deal
Wed, Feb 4 - Mon, Feb 9
Delta Logo
6:00 am - 2:21 pmMDW-SDQ
6h 21m1 stop
Delta Logo
7:05 am - 5:45 pmSDQ-MDW
12h 40m2 stops
$478Delta
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Thu, Feb 5 - Wed, Feb 18
Frontier Logo
6:15 am - 4:49 pmMDW-SDQ
8h 34m1 stop
Frontier Logo
10:41 am - 10:12 pmSDQ-MDW
13h 31m2 stops
$623Frontier
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Mon, Dec 29 - Tue, Dec 30
Frontier Logo
6:12 am - 3:24 pmMDW-SDQ
7h 12m1 stop
Frontier Logo
12:35 pm - 9:58 pmSDQ-MDW
11h 23m1 stop
$629Frontier
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Thu, Dec 25 - Tue, Dec 30
Frontier Logo
6:33 pm - 11:20 amMDW-SDQ
14h 47m2 stops
Frontier Logo
12:35 pm - 9:58 pmSDQ-MDW
11h 23m1 stop
$688Frontier
Find Deal
Thu, Dec 25 - Tue, Dec 30

Delta flights from Chicago Midway Airport to Santo Domingo

Our best Delta deals on Chicago Midway Airport to Santo Domingo flight tickets
Delta
Jan 25
MDW9:34 amChicago Midway
12h 58m
2 stops
SDQ12:32 amSanto Domingo Las Americas
Jan 27
SDQ7:31 amSanto Domingo Las Americas
16h 55m
2 stops
MDW10:26 pmChicago Midway
$434
Find similar
Delta
Nov 13
MDW9:34 amChicago Midway
14h 02m
2 stops
SDQ1:36 amSanto Domingo Las Americas
Nov 17
SDQ6:45 amSanto Domingo Las Americas
13h 23m
2 stops
MDW6:08 pmChicago Midway
$444
Find similar
Delta
Dec 6
MDW9:29 amChicago Midway
14h 19m
2 stops
SDQ1:48 amSanto Domingo Las Americas
Dec 14
SDQ3:57 pmSanto Domingo Las Americas
9h 50m
1 stop
MDW11:47 pmChicago Midway
$473
Find similar

Frontier flights from Chicago Midway Airport to Santo Domingo

Our best Frontier deals on Chicago Midway Airport to Santo Domingo flight tickets
Frontier
Dec 29
MDW6:15 amChicago Midway
8h 34m
1 stop
SDQ4:49 pmSanto Domingo Las Americas
Dec 30
SDQ10:41 amSanto Domingo Las Americas
13h 31m
2 stops
MDW10:12 pmChicago Midway
$623
Find similar
Frontier
Dec 25
MDW6:12 amChicago Midway
7h 12m
1 stop
SDQ3:24 pmSanto Domingo Las Americas
Dec 30
SDQ12:35 pmSanto Domingo Las Americas
11h 23m
1 stop
MDW9:58 pmChicago Midway
$629
Find similar
Frontier
Dec 25
MDW6:33 pmChicago Midway
14h 47m
2 stops
SDQ11:20 amSanto Domingo Las Americas
Dec 30
SDQ12:35 pmSanto Domingo Las Americas
11h 23m
1 stop
MDW9:58 pmChicago Midway
$688
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Santo Domingo 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, momondo users made 832,500 searches. Data last updated November 6, 2025.
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 12/6

2:59 pm-9:45 pm

1 stop28h 46m

Santo Domingo Las Americas

Sat 12/13

3:35 pm-10:30 pm

1 stop8h 55m

$323

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/4

2:16 pm-11:20 am

1 stop19h 04m

Santo Domingo Las Americas

Wed 1/14

10:19 am-2:47 pm

1 stop30h 28m

$372

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/4

2:16 pm-11:20 am

1 stop19h 04m

Santo Domingo Las Americas

Wed 1/14

10:19 am-9:31 pm

2 stops13h 12m

$401

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 1/25

9:34 am-12:32 am

2 stops12h 58m

Santo Domingo Las Americas

Tue 1/27

7:31 am-10:26 pm

2 stops16h 55m

$434

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 12/6

9:29 am-1:48 am

2 stops14h 19m

Santo Domingo Las Americas

Sun 12/14

3:57 pm-11:47 pm

1 stop9h 50m

$473

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 2/4

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Mon 2/9

3:46 pm-10:26 pm

1 stop8h 40m

$474

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 2/5

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 2/18

7:05 am-5:45 pm

2 stops12h 40m

$478

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 12/29

6:15 am-4:49 pm

1 stop8h 34m

Santo Domingo Las Americas

Tue 12/30

10:41 am-10:12 pm

2 stops13h 31m

$623

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 12/25

6:12 am-3:24 pm

1 stop7h 12m

Santo Domingo Las Americas

Tue 12/30

12:35 pm-9:58 pm

1 stop11h 23m

$629

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 12/25

6:33 pm-11:20 am

2 stops14h 47m

Santo Domingo Las Americas

Tue 12/30

12:35 pm-9:58 pm

1 stop11h 23m

$688

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Santo Domingo from

How to get the cheapest flight ticket from Chicago Midway Airport to Santo Domingo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Santo Domingo?

Our data shows that Tuesday is the least expensive day to fly to Santo Domingo. Tickets to fly out on this day can be as low as $451. The most expensive day to fly to Santo Domingo is Friday, with ticket prices averaging around $561.

What is the cheapest time of day to depart on your flight to Santo Domingo?

The cheapest time of day to fly to Santo Domingo is in the evening when flights can be purchased for as low as $386. Try not to purchase tickets in the morning because they tend to be around $521. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Chicago Midway Airport to Santo Domingo flights?

You could potentially save up to 32% on your flight if you consider stops on a Chicago Midway Airport to Santo Domingo flight.

When to book flights from Chicago Midway Airport to Santo Domingo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Santo Domingo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Santo Domingo (MDW to SDQ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Santo Domingo

Direct flights

None
There are no direct flights from Chicago Midway Airport to Santo Domingo. There are no popular flight routes from Chicago Midway Airport to Santo Domingo.
Search flight deals

  • How far is Chicago Midway to Santo Domingo Las Americas by plane?

    The distance between Chicago Midway and Santo Domingo Las Americas is about 1920.0 mi. Typically, this will take 6h 15m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to Santo Domingo Las Americas Airport?

    Prices for flights from Chicago Midway Airport to Santo Domingo Las Americas Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Santo Domingo Las Americas Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Santo Domingo Las Americas Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Santo Domingo Las Americas Airport.

  • What documentation or ID do you need to fly to Santo Domingo Las Americas Airport?

    The necessary travel and health documents for your Santo Domingo Las Americas Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to Santo Domingo?

Best airlines flying from Chicago Midway Airport to Santo Domingo

Compare and see reviews for airlines that fly from Chicago Midway Airport to Santo Domingo with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $406Free CancellationRating
7.9
8,001 reviews
Search Delta flights

Traveling to a place near Santo Domingo?

Book flights to Santo Domingo if you plan to visit one of these locations
Juan Dolio

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Santo Domingo?

It is quick and easy to find Chicago to Santo Domingo flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Santo Domingo that suits you.

Can I find flights from Chicago to Santo Domingo with flexible booking policies on momondo?

Yes. All flights to Santo Domingo from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Santo Domingo?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Santo Domingo.

I’m not ready to book a flight from Chicago to Santo Domingo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Santo Domingo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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