$141 Cheap Flights from Punta Cana (PUJ) to Chicago (MDW)

View $141 flight on Sun, Jun 8, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Punta Cana to Chicago (PUJ-MDW)

Prices were available within the past 7 days and start at $141 for one-way flights and $263 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Jul 4 - Wed, Jul 9
PUJ
Punta Cana
MDW
Chicago
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Punta Cana to Chicago, returning Wed, Jul 9, priced at $263 found 2 days ago
Southwest Airlines
Fri, Jul 4 - Wed, Jul 9
PUJ
Punta Cana
MDW
Chicago
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Punta Cana to Chicago, returning Wed, Jul 9, priced at $310 found 2 days ago
Delta
Sat, May 3 - Wed, May 7
PUJ
Punta Cana
MDW
Chicago
$360 Roundtrip, found 1 hour ago
$360
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 3 from Punta Cana to Chicago, returning Wed, May 7, priced at $360 found 1 hour ago
Delta
Sat, Apr 26 - Sat, May 3
PUJ
Punta Cana
MDW
Chicago
$372 Roundtrip, found 2 days ago
$372
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Apr 26 from Punta Cana to Chicago, returning Sat, May 3, priced at $372 found 2 days ago
Frontier Airlines
Thu, Jul 3 - Sun, Jul 6
PUJ
Punta Cana
MDW
Chicago
$374 Roundtrip, found 1 day ago
$374
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Punta Cana to Chicago, returning Sun, Jul 6, priced at $374 found 1 day ago
Frontier Airlines
Tue, Jul 15 - Sun, Jul 20
PUJ
Punta Cana
MDW
Chicago
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Punta Cana to Chicago, returning Sun, Jul 20, priced at $382 found 3 days ago
Southwest Airlines
Fri, Jul 4 - Mon, Jul 7
PUJ
Punta Cana
MDW
Chicago
$397 Roundtrip, found 1 day ago
$397
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Punta Cana to Chicago, returning Mon, Jul 7, priced at $397 found 1 day ago
Frontier Airlines
Wed, Jul 2 - Sun, Jul 6
PUJ
Punta Cana
MDW
Chicago
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 2 from Punta Cana to Chicago, returning Sun, Jul 6, priced at $406 found 1 day ago
Southwest Airlines
Fri, Jul 4 - Tue, Jul 8
PUJ
Punta Cana
MDW
Chicago
$410 Roundtrip, found 9 hours ago
$410
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Punta Cana to Chicago, returning Tue, Jul 8, priced at $410 found 9 hours ago
Southwest Airlines
Fri, Jul 4 - Tue, Jul 8
PUJ
Punta Cana
MDW
Chicago
$415 Roundtrip, found 9 hours ago
$415
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Punta Cana to Chicago, returning Tue, Jul 8, priced at $415 found 9 hours ago

Frequently asked questions

How much does a flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) cost?
Cheap round-trip flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) start from $450. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving PUJ on May 10 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from PUJ to MDW?
The cheapest flights from PUJ to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Take a direct flight with Southwest Airlines and head straight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from PUJ to MDW?
With tickets starting at $251 for a one-way flight from PUJ to MDW, Southwest Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PUJ on May 17 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
On average you can take your pick of 1 direct weekly flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW). For greater flexibility, consider flights with layovers. Just enter your details on Expedia and then filter your search results to show one or two stops.
What are the most popular departure times for flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Flights between PUJ and MDW tend to be busiest at 5 PM. If you want a more relaxed atmosphere and potentially cheaper tickets, choose a departure that’s outside typical rush times.
What day of the week has the most flights from PUJ to MDW?
Saturday has the most flights from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW). Consider jetting off on this day and you’ll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
The earliest flight taking off from Punta Cana Intl. Airport (PUJ) is at around 5:00PM UTC-4. Catch this flight and you’ll reach Midway Intl. Airport (MDW) at approximately 8:00PM UTC-6. The total flight duration is 5h.
How long does it take to fly from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
It usually takes 5 hours to fly the 1,950 mi from PUJ to MDW.
What is the best time to fly from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Select a flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Punta Cana Intl. Airport (PUJ)?
If you’re traveling on a direct flight from Punta Cana Intl. Airport (PUJ) to Chicago, you can arrive at either O’Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from PUJ to MDW are usually more expensive. To lock in the cheapest rates, start looking for flights as early as possible. That said, if you’re flexible with your travel plans, you may land a cheap ticket just before your departure.
Is it cheaper to book a PUJ to MDW flight and hotel package?
Opting for a PUJ to MDW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our wide range of accommodations and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Punta Cana Intl. Airport (PUJ) to Midway Intl. Airport (MDW)?
Typically, you’re able to cancel or reschedule your PUJ to MDW flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline’s fees and policies on flight changes, or if you’d like further information, go to our Customer Service portal.
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