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Cheap flights from Chicago Midway Airport to Punta Cana from $156

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 10/25. 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

Multiple Airlines Logo
12:18 pm - 4:31 pmMDW-PUJ
27h 13m1 stop
Multiple Airlines Logo
9:38 am - 9:22 pmPUJ-MDW
12h 44m1 stop
$334Multiple Airlines
Find Deal
Fri, Oct 24 - Sat, Nov 1
Southwest Logo
5:25 am - 2:10 pmMDW-PUJ
7h 45m1 stop
Southwest Logo
1:40 pm - 10:35 pmPUJ-MDW
9h 55m1 stop
$357Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
Delta Logo
6:00 am - 2:31 pmMDW-PUJ
7h 31m1 stop
Delta Logo
2:49 pm - 10:14 pmPUJ-MDW
8h 25m1 stop
$360Delta
Find Deal
Sun, Oct 26 - Fri, Oct 31
Southwest Logo
6:25 am - 2:20 pmMDW-PUJ
6h 55m1 stop
Southwest Logo
2:45 pm - 11:15 pmPUJ-MDW
9h 30m2 stops
$361Southwest
Find Deal
Sun, Oct 26 - Thu, Oct 30
Multiple Airlines Logo
12:18 pm - 4:31 pmMDW-PUJ
27h 13m1 stop
Multiple Airlines Logo
9:38 am - 6:39 pmPUJ-MDW
10h 01m2 stops
$362Multiple Airlines
Find Deal
Fri, Oct 24 - Sat, Nov 1
Delta Logo
6:00 am - 4:18 pmMDW-PUJ
8h 18m1 stop
Delta Logo
2:38 pm - 11:32 pmPUJ-MDW
10h 54m1 stop
$363Delta
Find Deal
Sun, Nov 16 - Thu, Nov 20
Delta Logo
6:45 pm - 2:30 pmMDW-PUJ
17h 45m1 stop
Delta Logo
5:11 pm - 8:54 amPUJ-MDW
17h 43m1 stop
$365Delta
Find Deal
Sun, Jan 11 - Thu, Jan 15
Delta Logo
12:47 pm - 1:26 pmMDW-PUJ
22h 39m2 stops
Delta Logo
5:03 pm - 11:32 pmPUJ-MDW
8h 29m1 stop
$368Delta
Find Deal
Tue, Nov 11 - Tue, Nov 18
Frontier Logo
6:15 am - 2:22 pmMDW-PUJ
7h 07m1 stop
Frontier Logo
3:32 pm - 10:47 pmPUJ-MDW
8h 15m1 stop
$383Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
6:00 am - 3:24 pmMDW-PUJ
7h 24m1 stop
Frontier Logo
4:34 pm - 11:26 pmPUJ-MDW
8h 52m1 stop
$385Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17

Delta flights from Chicago Midway Airport to Punta Cana

Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets
Delta
Oct 26
MDW6:00 amChicago Midway
7h 31m
1 stop
PUJ2:31 pmPunta Cana
Oct 31
PUJ2:49 pmPunta Cana
8h 25m
1 stop
MDW10:14 pmChicago Midway
$360
Find similar
Delta
Nov 16
MDW6:00 amChicago Midway
8h 18m
1 stop
PUJ4:18 pmPunta Cana
Nov 20
PUJ2:38 pmPunta Cana
10h 54m
1 stop
MDW11:32 pmChicago Midway
$363
Find similar
Delta
Jan 11
MDW6:45 pmChicago Midway
17h 45m
1 stop
PUJ2:30 pmPunta Cana
Jan 15
PUJ5:11 pmPunta Cana
17h 43m
1 stop
MDW8:54 amChicago Midway
$365
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
MDW6:15 amChicago Midway
7h 07m
1 stop
PUJ2:22 pmPunta Cana
Oct 25
PUJ3:32 pmPunta Cana
8h 15m
1 stop
MDW10:47 pmChicago Midway
$383
Find similar
Frontier
Jan 10
MDW6:00 amChicago Midway
7h 24m
1 stop
PUJ3:24 pmPunta Cana
Jan 17
PUJ4:34 pmPunta Cana
8h 52m
1 stop
MDW11:26 pmChicago Midway
$385
Find similar
Frontier
Oct 25
MDW6:15 amChicago Midway
7h 07m
1 stop
PUJ2:22 pmPunta Cana
Oct 30
PUJ1:24 pmPunta Cana
9h 39m
2 stops
MDW10:03 pmChicago Midway
$391
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 September 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 10/24

12:18 pm-4:31 pm

1 stop27h 13m

Punta Cana

Sat 11/1

9:38 am-9:22 pm

1 stop12h 44m

$334

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 10/14

5:25 am-2:10 pm

1 stop7h 45m

Punta Cana

Tue 10/21

1:40 pm-10:35 pm

1 stop9h 55m

$357

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/26

6:00 am-2:31 pm

1 stop7h 31m

Punta Cana

Fri 10/31

2:49 pm-10:14 pm

1 stop8h 25m

$360

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 10/26

6:25 am-2:20 pm

1 stop6h 55m

Punta Cana

Thu 10/30

2:45 pm-11:15 pm

2 stops9h 30m

$361

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 10/24

12:18 pm-4:31 pm

1 stop27h 13m

Punta Cana

Sat 11/1

9:38 am-6:39 pm

2 stops10h 01m

$362

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 11/16

6:00 am-4:18 pm

1 stop8h 18m

Punta Cana

Thu 11/20

2:38 pm-11:32 pm

1 stop10h 54m

$363

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sun 1/11

6:45 pm-2:30 pm

1 stop17h 45m

Punta Cana

Thu 1/15

5:11 pm-8:54 am

1 stop17h 43m

$365

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 11/11

12:47 pm-1:26 pm

2 stops22h 39m

Punta Cana

Tue 11/18

5:03 pm-11:32 pm

1 stop8h 29m

$368

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 10/18

6:15 am-2:22 pm

1 stop7h 07m

Punta Cana

Sat 10/25

3:32 pm-10:47 pm

1 stop8h 15m

$383

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 1/10

6:00 am-3:24 pm

1 stop7h 24m

Punta Cana

Sat 1/17

4:34 pm-11:26 pm

1 stop8h 52m

$385

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 Tuesday when prices can be found for as low as $501. 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 $574.

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 $545 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

Fastest flight time

4h 15m

Direct flights

Mon, Thu, Sat and Sun

Airports in Punta Cana

1 airport
The fastest flight from Chicago Midway Airport to Punta Cana takes 4h 15m
Direct flights go from Chicago Midway Airport to Punta Cana on Monday, Thursday, Saturday and 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 24m.

  • 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
3,174 reviews
Search Frontier flights
SouthwestPriceFrom $495Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $539Free CancellationRating
7.9
7,957 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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