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Cheap flights from Chicago Midway Airport to Punta Cana from $160

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 9/29. 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

Delta Logo
6:00 am - 2:31 pmMDW-PUJ
7h 31m1 stop
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$343Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Delta Logo
6:23 pm - 2:31 pmMDW-PUJ
19h 08m2 stops
Delta Logo
1:53 pm - 1:08 pmPUJ-MDW
24h 15m2 stops
$347Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Delta Logo
6:00 am - 2:31 pmMDW-PUJ
7h 31m1 stop
Delta Logo
3:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$357Delta
Find Deal
Mon, Oct 27 - Wed, Nov 5
Frontier Logo
6:10 am - 2:07 pmMDW-PUJ
6h 57m1 stop
Frontier Logo
3:22 pm - 11:09 pmPUJ-MDW
8h 47m1 stop
$363Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:00 am - 2:50 pmMDW-PUJ
6h 50m1 stop
Frontier Logo
3:22 pm - 11:05 pmPUJ-MDW
9h 43m1 stop
$364Frontier
Find Deal
Sat, Dec 6 - Sat, Dec 13
Delta Logo
6:00 am - 1:15 pmMDW-PUJ
6h 15m1 stop
Delta Logo
1:07 pm - 9:10 pmPUJ-MDW
9h 03m1 stop
$368Delta
Find Deal
Mon, Sep 1 - Sat, Sep 13
Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
Southwest Logo
2:50 pm - 9:40 pmPUJ-MDW
7h 50m1 stop
$389Southwest
Find Deal
Mon, Aug 18 - Wed, Aug 27
Southwest Logo
5:05 am - 1:55 pmMDW-PUJ
7h 50m1 stop
Southwest Logo
3:05 pm - 8:05 amPUJ-MDW
18h 00m2 stops
$401Southwest
Find Deal
Mon, Aug 18 - Wed, Aug 27
Logo
4:24 pm - 11:45 amMDW-PUJ
18h 21m1 stop
Logo
12:40 pm - 8:53 amPUJ-MDW
21h 13m1 stop
$454
Find Deal
Mon, Sep 1 - Thu, Sep 11
Logo
4:24 pm - 11:45 amMDW-PUJ
18h 21m1 stop
Logo
12:40 pm - 7:23 amPUJ-MDW
19h 43m1 stop
$459
Find Deal
Mon, Sep 1 - Sun, Sep 14

Southwest flights from Chicago Midway Airport to Punta Cana

Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets
Southwest
Aug 10
MDW5:35 amChicago Midway
7h 30m
1 stop
PUJ2:05 pmPunta Cana
Aug 19
PUJ2:50 pmPunta Cana
7h 50m
1 stop
MDW9:40 pmChicago Midway
$373
Find similar
Southwest
Aug 18
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Aug 27
PUJ2:50 pmPunta Cana
7h 50m
1 stop
MDW9:40 pmChicago Midway
$389
Find similar
Southwest
Aug 18
MDW5:05 amChicago Midway
7h 50m
1 stop
PUJ1:55 pmPunta Cana
Aug 27
PUJ3:05 pmPunta Cana
18h 00m
2 stops
MDW8:05 amChicago Midway
$401
Find similar

Frontier flights from Chicago Midway Airport to Punta Cana

Our best Frontier deals on Chicago Midway Airport to Punta Cana flight tickets
Frontier
Oct 18
MDW6:10 amChicago Midway
6h 57m
1 stop
PUJ2:07 pmPunta Cana
Oct 25
PUJ3:22 pmPunta Cana
8h 47m
1 stop
MDW11:09 pmChicago Midway
$363
Find similar
Frontier
Dec 6
MDW6:00 amChicago Midway
6h 50m
1 stop
PUJ2:50 pmPunta Cana
Dec 13
PUJ3:22 pmPunta Cana
9h 43m
1 stop
MDW11:05 pmChicago Midway
$364
Find similar
Frontier
Aug 9
MDW9:12 pmChicago Midway
43h 03m
2 stops
PUJ5:15 pmPunta Cana
Aug 12
PUJ3:25 pmPunta Cana
20h 15m
1 stop
MDW10:40 amChicago Midway
$375
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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 August 2, 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

Mon 10/27

6:00 am-2:31 pm

1 stop7h 31m

Punta Cana

Thu 10/30

2:49 pm-10:14 pm

1 stop8h 25m

$343

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 10/27

6:23 pm-2:31 pm

2 stops19h 08m

Punta Cana

Thu 10/30

1:53 pm-1:08 pm

2 stops24h 15m

$347

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 10/27

6:00 am-2:31 pm

1 stop7h 31m

Punta Cana

Wed 11/5

3:49 pm-10:14 pm

1 stop8h 25m

$357

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:10 am-2:07 pm

1 stop6h 57m

Punta Cana

Sat 10/25

3:22 pm-11:09 pm

1 stop8h 47m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 12/6

6:00 am-2:50 pm

1 stop6h 50m

Punta Cana

Sat 12/13

3:22 pm-11:05 pm

1 stop9h 43m

$364

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/1

6:00 am-1:15 pm

1 stop6h 15m

Punta Cana

Sat 9/13

1:07 pm-9:10 pm

1 stop9h 03m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 8/18

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

Wed 8/27

2:50 pm-9:40 pm

1 stop7h 50m

$389

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 8/18

5:05 am-1:55 pm

1 stop7h 50m

Punta Cana

Wed 8/27

3:05 pm-8:05 am

2 stops18h 00m

$401

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/1

4:24 pm-11:45 am

1 stop18h 21m

Punta Cana

Thu 9/11

12:40 pm-8:53 am

1 stop21h 13m

$454

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 9/1

4:24 pm-11:45 am

1 stop18h 21m

Punta Cana

Sun 9/14

12:40 pm-7:23 am

1 stop19h 43m

$459

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 August, then October is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during October average around $471.

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 Tuesday when prices can be found for as low as $500. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Punta Cana on Thursday is $583.

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 $553 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 are 1 cabin classes 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

$160

Fastest flight time

6h 15m

Direct flights

Sun

Airports in Punta Cana

1 airport
The best one-way flight to Punta Cana from Chicago Midway Airport in the past 72 hours is $160. The best round-trip flight deal from Chicago Midway Airport to Punta Cana found on momondo in the last 72 hours is $343.
The fastest flight from Chicago Midway Airport to Punta Cana takes 6h 15m
Direct flights go from Chicago Midway Airport to Punta Cana on Sunday. The only airline offering direct flights is Southwest.
There is 1 airport near Punta Cana: 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 6h 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
3,241 reviews
Search Frontier flights
SouthwestPriceFrom $495Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $539Free CancellationRating
8.0
7,983 reviews
Search Delta flights

  • Southwest Flights From Chicago Midway Airport to Punta Cana

    Southwest operates around 4 flights from Chicago Midway Airport to Punta Cana every week. The average price of these flights found in the last 72 hours has been $741, but momondo users have found Southwest deals from Chicago Midway Airport to Punta Cana from as low as $495 round-trip. Southwest has been scored 8.0/10 in 4,246 reviews.

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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