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Cheap flights from Chicago Midway Airport to Punta Cana from $139

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 4/11. 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
2:19 pm - 4:36 pm
MDW
-
PUJ
24h 17m
2 stops
Multiple Airlines Logo
2:16 pm - 9:45 pm
PUJ
-
MDW
9h 29m
1 stop
$322Multiple Airlines
Mon, Mar 2 - Sat, Mar 7
Multiple Airlines Logo
2:19 pm - 4:36 pm
MDW
-
PUJ
24h 17m
2 stops
Multiple Airlines Logo
2:16 pm - 9:45 pm
PUJ
-
MDW
9h 29m
1 stop
$323Multiple Airlines
Mon, Mar 2 - Sat, Mar 7
Multiple Airlines Logo
6:48 pm - 4:31 pm
MDW
-
PUJ
20h 43m
1 stop
Multiple Airlines Logo
3:32 pm - 10:19 pm
PUJ
-
MDW
7h 47m
1 stop
$329Multiple Airlines
Wed, Mar 25 - Fri, Mar 27
Multiple Airlines Logo
6:25 am - 3:42 pm
MDW
-
PUJ
7h 17m
1 stop
Multiple Airlines Logo
5:47 pm - 7:07 pm
PUJ
-
MDW
27h 20m
2 stops
$331Multiple Airlines
Sat, Feb 28 - Tue, Mar 3
Multiple Airlines Logo
7:30 am - 4:36 pm
MDW
-
PUJ
31h 06m
2 stops
Multiple Airlines Logo
1:01 pm - 1:41 pm
PUJ
-
MDW
25h 40m
1 stop
$337Multiple Airlines
Tue, Mar 3 - Wed, Mar 11
Frontier Logo
6:00 am - 1:46 pm
MDW
-
PUJ
6h 46m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$339Frontier
Sat, May 9 - Sat, May 16
Frontier Logo
9:14 am - 9:57 am
MDW
-
PUJ
23h 43m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$344Frontier
Fri, Apr 17 - Sat, Apr 25
Multiple Airlines Logo
9:51 pm - 6:00 pm
MDW
-
PUJ
19h 09m
1 stop
Multiple Airlines Logo
3:32 pm - 10:19 pm
PUJ
-
MDW
7h 47m
1 stop
$355Multiple Airlines
Mon, Mar 23 - Fri, Mar 27
Frontier Logo
6:00 am - 10:07 am
MDW
-
PUJ
27h 07m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$356Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
6:00 am - 2:15 pm
MDW
-
PUJ
7h 15m
1 stop
Frontier Logo
2:56 pm - 10:19 pm
PUJ
-
MDW
8h 23m
1 stop
$360Frontier
Thu, Apr 9 - Sat, Apr 18

Delta flights from Chicago Midway Airport to Punta Cana

Our best Delta deals on Chicago Midway Airport to Punta Cana flight tickets
Delta
Apr 6
MDW7:20 pmChicago Midway
16h 45m
1 stop
PUJ1:05 pmPunta Cana
Apr 14
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
$373
Delta
Apr 13
MDW6:00 amChicago Midway
6h 21m
1 stop
PUJ1:21 pmPunta Cana
Apr 17
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
$381
Delta
Apr 6
MDW6:07 pmChicago Midway
17h 01m
2 stops
PUJ12:08 pmPunta Cana
Apr 14
PUJ3:57 pmPunta Cana
7h 31m
1 stop
MDW10:28 pmChicago Midway
$385

Southwest flights from Chicago Midway Airport to Punta Cana

Our best Southwest deals on Chicago Midway Airport to Punta Cana flight tickets
Southwest
Mar 9
MDW6:00 amChicago Midway
6h 40m
1 stop
PUJ1:40 pmPunta Cana
Mar 16
PUJ2:40 pmPunta Cana
5h 10m
MDW6:50 pmChicago Midway
$380
Southwest
Mar 9
MDW5:00 pmChicago Midway
18h 25m
2 stops
PUJ12:25 pmPunta Cana
Mar 11
PUJ2:35 pmPunta Cana
5h 05m
MDW6:40 pmChicago Midway
$391
Southwest
Mar 3
MDW5:00 amChicago Midway
7h 30m
1 stop
PUJ2:30 pmPunta Cana
Mar 11
PUJ1:25 pmPunta Cana
8h 25m
1 stop
MDW8:50 pmChicago Midway
$397

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 February 8, 2026.
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 3/2

2:19 pm-4:36 pm

2 stops24h 17m

Punta Cana

Sat 3/7

2:16 pm-9:45 pm

1 stop9h 29m

$322

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/2

2:19 pm-4:36 pm

2 stops24h 17m

Punta Cana

Sat 3/7

2:16 pm-9:45 pm

1 stop9h 29m

$323

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Wed 3/25

6:48 pm-4:31 pm

1 stop20h 43m

Punta Cana

Fri 3/27

3:32 pm-10:19 pm

1 stop7h 47m

$329

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 2/28

6:25 am-3:42 pm

1 stop7h 17m

Punta Cana

Tue 3/3

5:47 pm-7:07 pm

2 stops27h 20m

$331

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 3/3

7:30 am-4:36 pm

2 stops31h 06m

Punta Cana

Wed 3/11

1:01 pm-1:41 pm

1 stop25h 40m

$337

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/9

6:00 am-1:46 pm

1 stop6h 46m

Punta Cana

Sat 5/16

2:56 pm-10:19 pm

1 stop8h 23m

$339

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 4/17

9:14 am-9:57 am

1 stop23h 43m

Punta Cana

Sat 4/25

2:56 pm-10:19 pm

1 stop8h 23m

$344

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Mon 3/23

9:51 pm-6:00 pm

1 stop19h 09m

Punta Cana

Fri 3/27

3:32 pm-10:19 pm

1 stop7h 47m

$355

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 4/11

6:00 am-10:07 am

1 stop27h 07m

Punta Cana

Sat 4/18

2:56 pm-10:19 pm

1 stop8h 23m

$356

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 4/9

6:00 am-2:15 pm

1 stop7h 15m

Punta Cana

Sat 4/18

2:56 pm-10:19 pm

1 stop8h 23m

$360

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 April is your next best option. Flight prices from Chicago Midway Airport to Punta Cana during April average around $546.

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 $483. 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 $548.

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

In the evening 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 $376. Flying to Punta Cana in the evening 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 $527 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?

You could potentially save up to 9% on your flight if you consider stops on a Chicago Midway Airport to Punta Cana flight.

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

$579

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 $579
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
5.7
3,051 reviews
Search Frontier flights
SouthwestPriceFrom $421Free CancellationRating
8.0
4,281 reviews
Search Southwest flights
DeltaPriceFrom $539Free CancellationRating
7.9
8,174 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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