Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Punta Cana?

With an average price of $740 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Punta Cana with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $387 on average.

Does Southwest fly direct to Punta Cana from Chicago Midway Airport?

No, Southwest does not fly the route directly.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Punta Cana with Southwest?

On average, the cheapest day of the week to fly from Chicago Midway Airport to Punta Cana with Southwest is Tuesday, when prices are around $126. The most expensive day is generally Saturday, where the average price is around $349.

$166 Cheap Southwest Flights from Chicago Midway Airport to Punta Cana

MDW - PUJ

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Flight Deals

Cheap Southwest Flight Deals from Chicago Midway Airport to Punta Cana

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago Midway Airport to Punta Cana that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Chicago Midway Airport to Punta Cana

Sat, Jan 24 - Sat, Jan 31

8:15 am - 2:35 pmMDW-PUJ

4h 20mnonstop

3:00 pm - 5:55 pmPUJ-MDW

4h 55mnonstop

$353Southwest

Find Deal

Sat, Nov 15 - Sat, Nov 22

7:40 am - 4:05 pmMDW-PUJ

6h 25m1 stop

3:20 pm - 6:20 pmPUJ-MDW

5h 00mnonstop

$355Southwest

Find Deal

Sat, Jan 24 - Sat, Jan 31

5:10 am - 2:00 pmMDW-PUJ

6h 50m1 stop

3:00 pm - 5:55 pmPUJ-MDW

4h 55mnonstop

$358Southwest

Find Deal

Sat, Nov 29 - Sat, Dec 6

8:30 am - 2:50 pmMDW-PUJ

4h 20mnonstop

5:00 pm - 10:35 pmPUJ-MDW

7h 35m1 stop

$359Southwest

Find Deal

Wed, Nov 12 - Wed, Nov 19

5:05 am - 3:00 pmMDW-PUJ

7h 55m1 stop

2:40 pm - 9:05 pmPUJ-MDW

8h 25m1 stop

$361Southwest

Find Deal

Sat, Jan 10 - Sat, Jan 17

8:15 am - 2:35 pmMDW-PUJ

4h 20mnonstop

3:35 pm - 10:10 pmPUJ-MDW

8h 35m1 stop

$363Southwest

Find Deal

Tue, Dec 16 - Tue, Dec 23

5:05 am - 3:00 pmMDW-PUJ

7h 55m1 stop

4:10 pm - 11:05 pmPUJ-MDW

8h 55m1 stop

$364Southwest

Find Deal

Sat, Nov 15 - Sat, Nov 22

7:40 am - 4:05 pmMDW-PUJ

6h 25m1 stop

3:45 pm - 10:40 pmPUJ-MDW

8h 55m1 stop

$365Southwest

Find Deal

Sat, Jan 24 - Fri, Jan 30

5:10 am - 2:00 pmMDW-PUJ

6h 50m1 stop

2:40 pm - 9:00 pmPUJ-MDW

8h 20m1 stop

$368Southwest

Find Deal

Wed, Feb 4 - Wed, Feb 11

5:00 am - 2:30 pmMDW-PUJ

7h 30m1 stop

2:40 pm - 10:05 pmPUJ-MDW

9h 25m2 stops

$372Southwest

Find Deal

Useful Info

Low season	August
High season	July
Cheapest flight	$166
Average price round-trip	$482

Best time to beat the crowds but there is an average 2% increase in price.

Most popular time to fly and prices are also 17% lower on average.

Flight from Chicago Midway Airport to Punta Cana

(price for this month)

When to Book Flights with Southwest from Chicago Midway Airport to Punta Cana

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Punta Cana?
With an average price of $740 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Punta Cana with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $387 on average.
Does Southwest fly direct to Punta Cana from Chicago Midway Airport?
No, Southwest does not fly the route directly.
What’s the cheapest day of the week to fly from Chicago Midway Airport to Punta Cana with Southwest?
On average, the cheapest day of the week to fly from Chicago Midway Airport to Punta Cana with Southwest is Tuesday, when prices are around $126. The most expensive day is generally Saturday, where the average price is around $349.

8.0

Very good4,243 verified ratings

8.1Boarding

7.5Entertainment

8.6Crew

8.0Comfort

7.0Food

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Everything you need to know for your flight from Chicago Midway Airport to Punta Cana

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Cabin class types available on flights to Punta Cana

First Class flights from Chicago Midway Airport to Punta Cana

Business Class flights from Chicago Midway Airport to Punta Cana

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MDW - PUJ

$166 Find Cheap Southwest Flights from Chicago Midway Airport to Punta Cana

Search hundreds of travel sites at once for deals on Southwest flights from Chicago Midway Airport to Punta Cana

Cheap Southwest Flight Deals from Chicago Midway Airport to Punta Cana

Recent round-trip Southwest flight deals from Chicago Midway Airport to Punta Cana

Recent one-way Southwest flight deals from Chicago Midway Airport to Punta Cana

Recent last minute Southwest flight deals from Chicago Midway Airport to Punta Cana

Recent direct Southwest flight deals from Chicago Midway Airport to Punta Cana

Good to know

When to Book Flights with Southwest from Chicago Midway Airport to Punta Cana

FAQs for flying to Punta Cana with Southwest

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Punta Cana?

Does Southwest fly direct to Punta Cana from Chicago Midway Airport?

What’s the cheapest day of the week to fly from Chicago Midway Airport to Punta Cana with Southwest?

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Everything you need to know for your flight from Chicago Midway Airport to Punta Cana

Cabin class types available on flights to Punta Cana

Cabin classes available on flights to Chicago Midway Airport. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Punta Cana with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight

Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.