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Cheap flights from Chicago Midway Airport to the Dominican Republic from $145

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 3/1. 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
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
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
$314Multiple Airlines
Fri, Feb 6 - Fri, Feb 13
Frontier Logo
8:00 am - 4:15 pm
MDW
-
PUJ
30h 15m2 stops
Frontier Logo
4:52 pm - 7:59 pm
PUJ
-
MDW
29h 07m1 stop
$323Frontier
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
5:01 pm - 3:01 pm
MDW
-
PUJ
20h 00m1 stop
Multiple Airlines Logo
1:10 pm - 2:55 pm
PUJ
-
MDW
27h 45m1 stop
$325Multiple Airlines
Fri, Feb 6 - Fri, Feb 13
Frontier Logo
6:00 am - 3:36 pm
MDW
-
PUJ
7h 36m1 stop
Frontier Logo
4:52 pm - 7:59 pm
PUJ
-
MDW
29h 07m1 stop
$327Frontier
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
7:20 pm - 5:33 pm
MDW
-
PUJ
20h 13m1 stop
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$331Multiple Airlines
Mon, Jan 19 - Sat, Jan 24
Multiple Airlines Logo
3:01 pm - 4:31 pm
MDW
-
PUJ
23h 30m1 stop
Multiple Airlines Logo
1:01 pm - 6:54 pm
PUJ
-
MDW
7h 53m1 stop
$342Multiple Airlines
Fri, Jan 9 - Fri, Jan 16
Frontier Logo
6:10 am - 3:07 pm
MDW
-
PUJ
6h 57m1 stop
Frontier Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$346Frontier
Sat, Jan 17 - Sat, Jan 24
Delta Logo
6:00 am - 2:17 pm
MDW
-
SDQ
6h 17m1 stop
Delta Logo
3:42 pm - 10:42 pm
SDQ
-
MDW
9h 00m1 stop
$390Delta
Wed, Feb 18 - Fri, Feb 27
Delta Logo
6:45 am - 12:30 am
MDW
-
SDQ
15h 45m2 stops
Delta Logo
8:45 pm - 10:22 pm
SDQ
-
MDW
27h 37m2 stops
$394Delta
Wed, Jan 14 - Wed, Jan 21
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m1 stop
Delta Logo
3:42 pm - 10:42 pm
SDQ
-
MDW
9h 00m1 stop
$415Delta
Thu, Feb 5 - Wed, Feb 18

Frontier flights from Chicago Midway Airport to Dominican Republic

Our best Frontier deals on Chicago Midway Airport to Dominican Republic flight tickets
Frontier
Feb 21
MDW8:00 amChicago Midway
30h 15m
2 stops
PUJ4:15 pmPunta Cana
Feb 28
PUJ4:52 pmPunta Cana
29h 07m
1 stop
MDW7:59 pmChicago Midway
$323
Find similar
Frontier
Feb 21
MDW6:00 amChicago Midway
7h 36m
1 stop
PUJ3:36 pmPunta Cana
Feb 28
PUJ4:52 pmPunta Cana
29h 07m
1 stop
MDW7:59 pmChicago Midway
$327
Find similar
Frontier
Jan 17
MDW6:10 amChicago Midway
6h 57m
1 stop
PUJ3:07 pmPunta Cana
Jan 24
PUJ4:11 pmPunta Cana
21h 34m
1 stop
MDW11:45 amChicago Midway
$346
Find similar

Delta flights from Chicago Midway Airport to Dominican Republic

Our best Delta deals on Chicago Midway Airport to Dominican Republic flight tickets
Delta
Jan 18
MDW6:45 amChicago Midway
7h 56m
1 stop
PUJ4:41 pmPunta Cana
Jan 22
PUJ4:55 pmPunta Cana
7h 27m
1 stop
MDW10:22 pmChicago Midway
$366
Find similar
Delta
Jan 18
MDW6:14 pmChicago Midway
19h 16m
2 stops
PUJ3:30 pmPunta Cana
Jan 21
PUJ3:45 pmPunta Cana
23h 01m
2 stops
MDW12:46 pmChicago Midway
$370
Find similar
Delta
Jan 6
MDW6:45 amChicago Midway
6h 45m
1 stop
PUJ3:30 pmPunta Cana
Jan 13
PUJ3:45 pmPunta Cana
8h 22m
1 stop
MDW10:07 pmChicago Midway
$382
Find similar

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 December 17, 2025.
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

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/6

5:01 pm-3:01 pm

1 stop20h 00m

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

$314

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/21

8:00 am-4:15 pm

2 stops30h 15m

Punta Cana

Sat 2/28

4:52 pm-7:59 pm

1 stop29h 07m

$323

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 2/6

5:01 pm-3:01 pm

1 stop20h 00m

Punta Cana

Fri 2/13

1:10 pm-2:55 pm

1 stop27h 45m

$325

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/21

6:00 am-3:36 pm

1 stop7h 36m

Punta Cana

Sat 2/28

4:52 pm-7:59 pm

1 stop29h 07m

$327

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 1/19

7:20 pm-5:33 pm

1 stop20h 13m

Punta Cana

Sat 1/24

4:11 pm-11:45 am

1 stop21h 34m

$331

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 1/9

3:01 pm-4:31 pm

1 stop23h 30m

Punta Cana

Fri 1/16

1:01 pm-6:54 pm

1 stop7h 53m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/17

6:10 am-3:07 pm

1 stop6h 57m

Punta Cana

Sat 1/24

4:11 pm-11:45 am

1 stop21h 34m

$346

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 2/18

6:00 am-2:17 pm

1 stop6h 17m

Santo Domingo Las Americas

Fri 2/27

3:42 pm-10:42 pm

1 stop9h 00m

$390

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Wed 1/14

6:45 am-12:30 am

2 stops15h 45m

Santo Domingo Las Americas

Wed 1/21

8:45 pm-10:22 pm

2 stops27h 37m

$394

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

3:42 pm-10:42 pm

1 stop9h 00m

$415

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 February is also very affordable. Most momondo users find prices during this month for around $520.

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 Friday will generally be more expensive and average around $839. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Flying to Dominican Republic from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $281 when looking at flights departing in the evening. Flights in the morning are often more expensive with an average ticket price of $683.

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 4% 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

$381

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 $381
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
5.8
3,082 reviews
Search Frontier flights
DeltaPriceFrom $406Free CancellationRating
7.9
8,008 reviews
Search Delta flights
SouthwestPriceFrom $495Free 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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Popular flights according to clicks in the last 7 days on momondo
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