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Cheap flights from Chicago Midway Airport to the Dominican Republic from $139

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 4/11. 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 the Dominican Republic

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 4:29 pm
MDW
-
SDQ
9h 29m
1 stop
Multiple Airlines Logo
10:46 am - 8:53 pm
SDQ
-
MDW
11h 07m
1 stop
$317Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Frontier Logo
6:25 am - 3:42 pm
MDW
-
PUJ
7h 17m
1 stop
Frontier Logo
4:32 pm - 10:19 pm
PUJ
-
MDW
7h 47m
1 stop
$322Frontier
Sat, Feb 28 - Fri, Mar 6
Multiple Airlines Logo
6:25 am - 3:42 pm
MDW
-
PUJ
7h 17m
1 stop
Multiple Airlines Logo
5:47 pm - 7:07 pm
PUJ
-
MDW
27h 20m
2 stops
$331Multiple Airlines
Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
6:00 am - 4:36 pm
MDW
-
PUJ
32h 36m
2 stops
Multiple Airlines Logo
2:16 pm - 9:45 pm
PUJ
-
MDW
9h 29m
1 stop
$336Multiple Airlines
Fri, Feb 27 - Sat, Mar 7
Multiple Airlines Logo
6:05 am - 7:54 pm
MDW
-
PUJ
12h 49m
2 stops
Multiple Airlines Logo
3:32 pm - 10:19 pm
PUJ
-
MDW
7h 47m
1 stop
$337Multiple Airlines
Wed, Mar 11 - Wed, Mar 25
Frontier Logo
6:00 am - 1:46 pm
MDW
-
PUJ
6h 46m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$339Frontier
Sat, May 9 - Sat, May 16
Frontier Logo
9:14 am - 9:57 am
MDW
-
PUJ
23h 43m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$344Frontier
Fri, Apr 17 - Sat, Apr 25
Delta Logo
1:29 pm - 1:34 am
MDW
-
STI
10h 05m
2 stops
Delta Logo
6:33 am - 10:31 pm
STI
-
MDW
16h 58m
2 stops
$519Delta
Mon, Mar 2 - Tue, Mar 10
Delta Logo
6:00 am - 7:15 pm
MDW
-
STI
12h 15m
2 stops
Delta Logo
6:33 am - 10:31 pm
STI
-
MDW
16h 58m
2 stops
$538Delta
Wed, Mar 11 - Wed, Mar 18
Delta Logo
9:34 am - 1:34 am
MDW
-
STI
14h 00m
2 stops
Delta Logo
8:40 pm - 12:29 pm
STI
-
MDW
16h 49m
2 stops
$548Delta
Thu, Mar 5 - Mon, Mar 9

Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Southwest
Mar 9
MDW6:00 amChicago Midway
6h 40m
1 stop
PUJ1:40 pmPunta Cana
Mar 16
PUJ2:40 pmPunta Cana
5h 10m
MDW6:50 pmChicago Midway
$380
Southwest
May 17
MDW8:50 pmChicago Midway
17h 10m
2 stops
PUJ3:00 pmPunta Cana
May 21
PUJ1:40 pmPunta Cana
9h 40m
1 stop
MDW10:20 pmChicago Midway
$385
Southwest
Mar 10
MDW9:15 amChicago Midway
4h 15m
PUJ2:30 pmPunta Cana
Mar 17
PUJ1:25 pmPunta Cana
10h 15m
1 stop
MDW10:40 pmChicago Midway
$406

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets
Delta
Apr 13
MDW6:00 amChicago Midway
7h 32m
1 stop
PUJ2:32 pmPunta Cana
Apr 17
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
$381
Delta
Apr 12
MDW6:34 pmChicago Midway
17h 20m
1 stop
PUJ12:54 pmPunta Cana
Apr 21
PUJ2:46 pmPunta Cana
8h 42m
1 stop
MDW10:28 pmChicago Midway
$391
Delta
Apr 12
MDW6:34 pmChicago Midway
17h 47m
2 stops
PUJ1:21 pmPunta Cana
Apr 21
PUJ2:46 pmPunta Cana
19h 01m
2 stops
MDW8:47 amChicago Midway
$395

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 February 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

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Mon 3/9

6:00 am-4:29 pm

1 stop9h 29m

Santo Domingo Las Americas

Mon 3/16

10:46 am-8:53 pm

1 stop11h 07m

$317

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/28

6:25 am-3:42 pm

1 stop7h 17m

Punta Cana

Fri 3/6

4:32 pm-10:19 pm

1 stop7h 47m

$322

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/28

6:25 am-3:42 pm

1 stop7h 17m

Punta Cana

Tue 3/3

5:47 pm-7:07 pm

2 stops27h 20m

$331

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/27

6:00 am-4:36 pm

2 stops32h 36m

Punta Cana

Sat 3/7

2:16 pm-9:45 pm

1 stop9h 29m

$336

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 3/11

6:05 am-7:54 pm

2 stops12h 49m

Punta Cana

Wed 3/25

3:32 pm-10:19 pm

1 stop7h 47m

$337

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/9

6:00 am-1:46 pm

1 stop6h 46m

Punta Cana

Sat 5/16

2:56 pm-10:19 pm

1 stop8h 23m

$339

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 4/17

9:14 am-9:57 am

1 stop23h 43m

Punta Cana

Sat 4/25

2:56 pm-10:19 pm

1 stop8h 23m

$344

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Mon 3/2

1:29 pm-1:34 am

2 stops10h 05m

Santiago de los Caballeros

Tue 3/10

6:33 am-10:31 pm

2 stops16h 58m

$519

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Wed 3/11

6:00 am-7:15 pm

2 stops12h 15m

Santiago de los Caballeros

Wed 3/18

6:33 am-10:31 pm

2 stops16h 58m

$538

ChicagoSantiago de los Caballeros

MDW - STI

MDWSTI

Chicago Midway

Thu 3/5

9:34 am-1:34 am

2 stops14h 00m

Santiago de los Caballeros

Mon 3/9

8:40 pm-12:29 pm

2 stops16h 49m

$548

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, October 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 $482. If you are unable to visit Dominican Republic during the month of October, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $546.

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 $614. 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 Wednesday will generally be more expensive and average around $856. 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 to Dominican Republic flights?

There is only 1 cabin class available to choose from on Chicago Midway 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?

You could potentially save up to 9% on your flight if you consider stops on a Chicago Midway Airport to Dominican Republic flight.

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

$579

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Dominican Republic

16 airports
The best flight deal from Chicago Midway Airport to Dominican Republic found on momondo in the last 72 hours is $579
The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 15m
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

  • 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 $370Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
DeltaPriceFrom $406Free CancellationRating
7.9
8,180 reviews
Search Delta flights
SouthwestPriceFrom $421Free CancellationRating
8.0
4,280 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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Popular flights according to clicks in the last 7 days on momondo
Flights to Punta Canafrom $186
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