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Cheap flights from Chicago Midway Airport to Punta Cana 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 Punta Cana 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 Punta Cana

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
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
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
$337Frontier
Sat, Feb 21 - Sat, Feb 28
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
Multiple Airlines Logo
3:10 pm - 2:09 pm
MDW
-
PUJ
20h 59m1 stop
Multiple Airlines Logo
6:49 pm - 12:02 am
PUJ
-
MDW
31h 13m2 stops
$345Multiple Airlines
Mon, Jan 5 - Mon, Jan 12
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
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
$348Frontier
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
8:19 pm - 11:40 am
MDW
-
PUJ
13h 21m1 stop
Multiple Airlines Logo
4:11 pm - 11:45 am
PUJ
-
MDW
21h 34m1 stop
$349Multiple Airlines
Sun, Jan 18 - Sat, Jan 24

Frontier flights from Chicago Midway Airport to Punta Cana

Our best Frontier deals on Chicago Midway Airport to Punta Cana flight tickets
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
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
$337
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 Punta Cana

Our best Delta deals on Chicago Midway Airport to Punta Cana 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 Punta Cana 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 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Punta Cana 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

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

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

$337

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

Mon 1/5

3:10 pm-2:09 pm

1 stop20h 59m

Punta Cana

Mon 1/12

6:49 pm-12:02 am

2 stops31h 13m

$345

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

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

$348

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/18

8:19 pm-11:40 am

1 stop13h 21m

Punta Cana

Sat 1/24

4:11 pm-11:45 am

1 stop21h 34m

$349

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 Punta Cana from

How to get the cheapest flight ticket from Chicago Midway Airport to Punta Cana

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 Punta Cana?

If you’re not able to fly to Punta Cana in October, then February is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during February average around $520.

What is the cheapest day to depart on your flight to Punta Cana?

The cheapest day to depart from Chicago Midway Airport to Punta Cana is on a Monday when prices can be found for as low as $494. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Sunday is $559.

What is the cheapest time of day to depart on your flight to Punta Cana?

At noon is the cheapest time of day to fly from Chicago Midway Airport to Punta Cana when you can find flight prices for as low as $341. Flying to Punta Cana at noon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Punta Cana, so prices are often more expensive at around $533 per ticket.

What is the cheapest Chicago Midway to Punta Cana flight route?

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

What cabin class options are available on Chicago Midway to Punta Cana flights?

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

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

When to book flights from Chicago Midway Airport to Punta Cana

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

Cheap Chicago Midway Airport to Punta Cana (MDW to PUJ) flight deals and tips

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

Best Price Found

$381

Fastest flight time

4h 15m

Direct flights

Every day

Airports in Punta Cana

1 airport
The best flight deal from Chicago Midway Airport to Punta Cana found on momondo in the last 72 hours is $381
The fastest flight from Chicago Midway Airport to Punta Cana takes 4h 15m
Direct flights go from Chicago Midway Airport to Punta Cana every day.
There is 1 airport in Punta Cana. From Chicago Midway Airport there are direct flights to Punta Cana (PUJ).
Search flight deals

  • How far is Chicago Midway to Punta Cana by plane?

    The straight-line distance from Chicago Midway to Punta Cana is 1957.5 mi. A reasonable flight in good conditions will take 4h 15m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Punta Cana Airport?

    Prices for flights from Chicago Midway Airport to Punta Cana Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Punta Cana Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Punta Cana Airport?

    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 Punta Cana Airport.

  • What documentation or ID do you need to fly to Punta Cana Airport?

    The necessary travel and health documents for your Punta Cana 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 plane model from Chicago Midway Airport to Punta Cana?

  • What is the most popular airline from Chicago Midway Airport to Punta Cana?

Best airlines flying from Chicago Midway Airport to Punta Cana

Compare and see reviews for airlines that fly from Chicago Midway Airport to Punta Cana with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $370Free CancellationRating
5.8
3,082 reviews
Search Frontier flights
SouthwestPriceFrom $495Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
DeltaPriceFrom $539Free CancellationRating
7.9
8,010 reviews
Search Delta flights

Traveling to a place near Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Bavaro

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Punta Cana?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Punta Cana from Chicago.

Can I find flights from Chicago to Punta Cana with flexible booking policies on momondo?

All flight searches from Chicago to Punta Cana on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Punta Cana?

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 Punta Cana.

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

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

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