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Cheap flights from Chicago Midway Airport to the Dominican Republic from $159

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 the Dominican Republic departing on 8/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to the Dominican Republic

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
Delta Logo
2:53 pm - 10:45 pm
SDQ
-
MDW
8h 52m
1 stop
$408Delta
Sun, Sep 6 - Tue, Sep 15
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
Delta Logo
2:53 pm - 10:45 pm
SDQ
-
MDW
8h 52m
1 stop
$439Delta
Sun, Sep 6 - Tue, Sep 15
Delta Logo
6:05 am - 6:06 pm
MDW
-
SDQ
11h 01m
2 stops
Delta Logo
2:53 pm - 10:45 pm
SDQ
-
MDW
8h 52m
1 stop
$444Delta
Sun, Sep 6 - Tue, Sep 15
Southwest Logo
6:15 am - 1:20 pm
MDW
-
PUJ
6h 05m
1 stop
Southwest Logo
1:45 pm - 9:00 pm
PUJ
-
MDW
8h 15m
1 stop
$461Southwest
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
11:50 am - 2:27 pm
MDW
-
PUJ
25h 37m
1 stop
Frontier Logo
11:39 am - 10:47 pm
PUJ
-
MDW
12h 08m
2 stops
$464Frontier
Fri, Sep 4 - Sun, Sep 6
Delta Logo
6:00 am - 2:25 pm
MDW
-
PUJ
6h 25m
1 stop
Delta Logo
3:45 pm - 8:49 am
PUJ
-
MDW
19h 04m
1 stop
$465Delta
Mon, Nov 30 - Sat, Dec 5
Southwest Logo
6:15 am - 1:20 pm
MDW
-
PUJ
6h 05m
1 stop
Southwest Logo
1:45 pm - 9:50 pm
PUJ
-
MDW
9h 05m
2 stops
$466Southwest
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
3:31 pm - 9:51 am
PUJ
-
MDW
19h 20m
1 stop
$468Frontier
Tue, Jul 28 - Wed, Aug 5
Southwest Logo
7:55 pm - 1:20 pm
MDW
-
PUJ
16h 25m
2 stops
Southwest Logo
2:45 pm - 10:00 pm
PUJ
-
MDW
8h 15m
1 stop
$479Southwest
Mon, Sep 28 - Fri, Oct 2
Frontier Logo
6:05 am - 2:21 pm
MDW
-
PUJ
7h 16m
1 stop
Frontier Logo
9:29 pm - 9:51 am
PUJ
-
MDW
37h 22m
2 stops
$480Frontier
Tue, Aug 4 - Tue, Aug 11

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Frontier flights from Chicago Midway Airport to Dominican Republic

Our best Frontier deals on Chicago Midway Airport to Dominican Republic flight tickets
Frontier
Sep 4
MDW11:50 amChicago Midway
25h 37m
1 stop
PUJ2:27 pmPunta Cana
Sep 6
PUJ11:39 amPunta Cana
12h 08m
2 stops
MDW10:47 pmChicago Midway
$464
Frontier
Jul 28
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
Aug 5
PUJ3:31 pmPunta Cana
19h 20m
1 stop
MDW9:51 amChicago Midway
$468
Frontier
Aug 4
MDW6:05 amChicago Midway
7h 16m
1 stop
PUJ2:21 pmPunta Cana
Aug 11
PUJ9:29 pmPunta Cana
37h 22m
2 stops
MDW9:51 amChicago Midway
$480

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets
Delta
Sep 6
MDW6:05 amChicago Midway
6h 23m
1 stop
SDQ1:28 pmSanto Domingo Las Americas
Sep 15
SDQ2:53 pmSanto Domingo Las Americas
8h 52m
1 stop
MDW10:45 pmChicago Midway
$408
Delta
Sep 6
MDW6:05 amChicago Midway
6h 23m
1 stop
SDQ1:28 pmSanto Domingo Las Americas
Sep 15
SDQ2:53 pmSanto Domingo Las Americas
8h 52m
1 stop
MDW10:45 pmChicago Midway
$439
Delta
Sep 6
MDW6:05 amChicago Midway
11h 01m
2 stops
SDQ6:06 pmSanto Domingo Las Americas
Sep 15
SDQ2:53 pmSanto Domingo Las Americas
8h 52m
1 stop
MDW10:45 pmChicago Midway
$444

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Dominican Republic 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 July 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to the Dominican Republic that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 9/6

6:05 am-1:28 pm

1 stop6h 23m

Santo Domingo Las Americas

Tue 9/15

2:53 pm-10:45 pm

1 stop8h 52m

$408

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 9/6

6:05 am-1:28 pm

1 stop6h 23m

Santo Domingo Las Americas

Tue 9/15

2:53 pm-10:45 pm

1 stop8h 52m

$439

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sun 9/6

6:05 am-6:06 pm

2 stops11h 01m

Santo Domingo Las Americas

Tue 9/15

2:53 pm-10:45 pm

1 stop8h 52m

$444
Quickest round-trip

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 8/25

6:15 am-1:20 pm

1 stop6h 05m

Punta Cana

Tue 9/1

1:45 pm-9:00 pm

1 stop8h 15m

$461

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 9/4

11:50 am-2:27 pm

1 stop25h 37m

Punta Cana

Sun 9/6

11:39 am-10:47 pm

2 stops12h 08m

$464

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 11/30

6:00 am-2:25 pm

1 stop6h 25m

Punta Cana

Sat 12/5

3:45 pm-8:49 am

1 stop19h 04m

$465

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 8/25

6:15 am-1:20 pm

1 stop6h 05m

Punta Cana

Tue 9/1

1:45 pm-9:50 pm

2 stops9h 05m

$466

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 7/28

6:05 am-2:21 pm

1 stop7h 16m

Punta Cana

Wed 8/5

3:31 pm-9:51 am

1 stop19h 20m

$468

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/28

7:55 pm-1:20 pm

2 stops16h 25m

Punta Cana

Fri 10/2

2:45 pm-10:00 pm

1 stop8h 15m

$479

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 8/4

6:05 am-2:21 pm

1 stop7h 16m

Punta Cana

Tue 8/11

9:29 pm-9:51 am

2 stops37h 22m

$480

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 the Dominican Republic from

How to get the cheapest flight ticket from Chicago Midway Airport to Dominican Republic

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 month to fly to Dominican Republic?

In general, April is the cheapest month to fly from Chicago Midway Airport to Dominican Republic. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $190. If you are unable to visit Dominican Republic during the month of April, then departing from Chicago Midway Airport during the month November is also very affordable. Most momondo users find prices during this month for around $364.

What is the cheapest day to depart on your flight to Dominican Republic?

The cheapest day to depart on your flight to Dominican Republic is on a Saturday when prices can be found for as low as $635. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago Midway Airport to Dominican Republic on a Friday will generally be more expensive and average around $855. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest Chicago Midway to Dominican Republic flight route?

Fly from Chicago Midway to Punta Cana for the best Chicago Midway - Dominican Republic flight prices

What cabin class options are available on Chicago Midway Airport to Dominican Republic flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Dominican Republic flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Dominican Republic flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Dominican Republic.

Cheap Chicago Midway Airport to Dominican Republic flight deals and tips

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

Best Price Found

$338

Fastest flight time

4h 25m

Direct flights

Every day

Airports in Dominican Republic

16 airports
The best one-way flight to Dominican Republic from Chicago Midway Airport in the past 72 hours is $338. The best round-trip flight deal from Chicago Midway Airport to Dominican Republic found on momondo in the last 72 hours is $583.
The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 25m
Direct flights go from Chicago Midway Airport to Dominican Republic every day.
There are 16 airports in Dominican Republic. From Chicago Midway Airport there are direct flights to Punta Cana (PUJ).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to the Dominican Republic

  • When did momondo last update prices for flights from Chicago Midway Airport to Dominican Republic?

    Prices for flights from Chicago Midway Airport to Dominican Republic are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Dominican Republic?

  • How old do you have to be to fly from Chicago Midway Airport to Dominican Republic?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Dominican Republic.

  • What documentation or ID do you need to fly to Dominican Republic?

    The travel and health documents you'll need for your trip to Dominican Republic may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dominican Republic. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Dominican Republic?

Best airlines flying from Chicago Midway Airport to Dominican Republic

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dominican Republic with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $478Free CancellationRating
5.6
2,827 reviews
Search Frontier flights
SouthwestPriceFrom $503Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dominican Republic?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Dominican Republic. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Dominican Republic with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Dominican Republic from Chicago with this policy.

How can momondo help me find flights from Chicago to Dominican Republic?

momondo provides multiple filters to help you find the best flight to Dominican Republic from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Dominican Republic, momondo offers a useful price alert feature which will track prices for flights to Dominican Republic from Chicago and alert you when they change.

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Find better results for your trip to the Dominican Republic

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