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Cheap flights from Chicago Midway Airport to the Dominican Republic from $208

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 6/9. 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.
Frontier Logo
6:00 am - 2:30 pm
MDW
-
PUJ
7h 30m
1 stop
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$437Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
6:00 am - 11:54 am
MDW
-
PUJ
28h 54m
2 stops
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$447Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
6:00 am - 2:30 pm
MDW
-
PUJ
7h 30m
1 stop
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$466Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
6:00 am - 11:54 am
MDW
-
PUJ
28h 54m
2 stops
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$472Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
12:11 pm - 2:34 pm
MDW
-
PUJ
25h 23m
1 stop
Frontier Logo
3:39 pm - 11:09 am
PUJ
-
MDW
20h 30m
1 stop
$474Frontier
Thu, Aug 13 - Tue, Aug 18
Frontier Logo
11:59 am - 2:49 pm
MDW
-
PUJ
25h 50m
1 stop
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$480Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
6:00 am - 2:30 pm
MDW
-
PUJ
7h 30m
1 stop
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$481Frontier
Sat, Jul 4 - Sat, Jul 11
Frontier Logo
6:00 am - 11:54 am
MDW
-
PUJ
28h 54m
2 stops
Frontier Logo
3:44 pm - 11:07 am
PUJ
-
MDW
20h 23m
1 stop
$484Frontier
Sat, Jul 4 - Sat, Jul 11
Delta Logo
6:00 am - 1:17 pm
MDW
-
SDQ
6h 17m
1 stop
Delta Logo
2:53 pm - 10:36 pm
SDQ
-
MDW
8h 43m
1 stop
$502Delta
Thu, Jul 23 - Mon, Aug 3
Delta Logo
6:05 am - 1:28 pm
MDW
-
SDQ
6h 23m
1 stop
Delta Logo
2:53 pm - 10:36 pm
SDQ
-
MDW
8h 43m
1 stop
$526Delta
Thu, Aug 13 - Mon, Aug 24

Frontier flights from Chicago Midway Airport to Dominican Republic

Our best Frontier deals on Chicago Midway Airport to Dominican Republic flight tickets
Frontier
Jul 4
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ2:30 pmPunta Cana
Jul 11
PUJ3:44 pmPunta Cana
20h 23m
1 stop
MDW11:07 amChicago Midway
$437
Frontier
Jul 4
MDW6:00 amChicago Midway
28h 54m
2 stops
PUJ11:54 amPunta Cana
Jul 11
PUJ3:44 pmPunta Cana
20h 23m
1 stop
MDW11:07 amChicago Midway
$447
Frontier
Jul 4
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ2:30 pmPunta Cana
Jul 11
PUJ3:44 pmPunta Cana
20h 23m
1 stop
MDW11:07 amChicago Midway
$466

Southwest flights from Chicago Midway Airport to Dominican Republic

Our best Southwest deals on Chicago Midway Airport to Dominican Republic flight tickets
Southwest
Jun 1
MDW8:35 pmChicago Midway
16h 40m
2 stops
PUJ2:15 pmPunta Cana
Jun 4
PUJ1:45 pmPunta Cana
7h 25m
1 stop
MDW8:10 pmChicago Midway
$705
Southwest
May 24
MDW6:40 amChicago Midway
7h 10m
1 stop
PUJ2:50 pmPunta Cana
May 28
PUJ1:40 pmPunta Cana
9h 40m
1 stop
MDW10:20 pmChicago Midway
$760
Southwest
May 24
MDW6:40 amChicago Midway
7h 10m
1 stop
PUJ2:50 pmPunta Cana
May 28
PUJ2:05 pmPunta Cana
18h 05m
2 stops
MDW7:10 amChicago Midway
$765

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 May 22, 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

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-2:30 pm

1 stop7h 30m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$437

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-11:54 am

2 stops28h 54m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$447

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-2:30 pm

1 stop7h 30m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$466

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-11:54 am

2 stops28h 54m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$472

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 8/13

12:11 pm-2:34 pm

1 stop25h 23m

Punta Cana

Tue 8/18

3:39 pm-11:09 am

1 stop20h 30m

$474

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

11:59 am-2:49 pm

1 stop25h 50m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$480

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-2:30 pm

1 stop7h 30m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$481

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 7/4

6:00 am-11:54 am

2 stops28h 54m

Punta Cana

Sat 7/11

3:44 pm-11:07 am

1 stop20h 23m

$484
Quickest round-trip

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 7/23

6:00 am-1:17 pm

1 stop6h 17m

Santo Domingo Las Americas

Mon 8/3

2:53 pm-10:36 pm

1 stop8h 43m

$502

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Thu 8/13

6:05 am-1:28 pm

1 stop6h 23m

Santo Domingo Las Americas

Mon 8/24

2:53 pm-10:36 pm

1 stop8h 43m

$526

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 March is also very affordable. Most momondo users find prices during this month for around $252.

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 Tuesday when prices can be found for as low as $605. 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 Sunday will generally be more expensive and average around $759. 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?

You could potentially save up to 44% 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

$605

Fastest flight time

4h 20m

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 $605
The fastest flight from Chicago Midway Airport to Dominican Republic takes 4h 20m
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 $370Free CancellationRating
5.6
2,940 reviews
Search Frontier flights
SouthwestPriceFrom $416Free CancellationRating
7.9
4,277 reviews
Search Southwest flights
DeltaPriceFrom $539Free CancellationRating
7.9
8,444 reviews
Search Delta 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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