PUJ - MDW

$235 Find Cheap Flights from Punta Cana to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$427
Typical prices: $353-$525
Delta
Mon 12/24Mon 1/1
PUJ - MDW • 1 stop
Cheapest one-way
$235
Typical prices: $292-$460
Delta
Sun 12/9
PUJ - MDW • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Punta Cana and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
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Top layover airports
Baltimore/Washington (BWI)
Cheapest • Avg $525 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 6h 45m (one-way)
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Insights
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We hope you love your trip to Chicago Midway Airport!
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Flight Deals

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

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

Recent round-trip flight deals from Punta Cana to Midway

Thu, Dec 24 - Fri, Jan 1
Delta Logo
3:40 pm - 10:22 pmPUJ  Punta Cana-MDW Chicago Midway
8h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:41 pmMDW  Chicago Midway-PUJ Punta Cana
8h 41m1 stop Atlanta Hartsfield-Jackson
$427Delta
Thu, Dec 24 - Fri, Jan 1
Delta Logo
4:45 pm - 10:22 pmPUJ  Punta Cana-MDW Chicago Midway
7h 37m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:41 pmMDW  Chicago Midway-PUJ Punta Cana
8h 41m1 stop Atlanta Hartsfield-Jackson
$427Delta
Thu, Oct 1 - Sat, Oct 17
Delta Logo
2:50 pm - 9:07 amPUJ  Punta Cana-MDW Chicago Midway
19h 17m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 12:40 pmMDW  Chicago Midway-PUJ Punta Cana
22h 13m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
$491Delta
Thu, Dec 24 - Fri, Jan 1
Delta Logo
3:40 pm - 10:22 pmPUJ  Punta Cana-MDW Chicago Midway
8h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 4:41 pmMDW  Chicago Midway-PUJ Punta Cana
8h 41m1 stop Atlanta Hartsfield-Jackson
$510Delta
Sat, Oct 3 - Sat, Oct 17
Delta Logo
1:07 pm - 9:07 amPUJ  Punta Cana-MDW Chicago Midway
21h 00m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 12:40 pmMDW  Chicago Midway-PUJ Punta Cana
22h 13m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
$551Delta
Tue, Oct 6 - Sat, Oct 17
Delta Logo
2:05 pm - 12:47 pmPUJ  Punta Cana-MDW Chicago Midway
23h 42m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 12:40 pmMDW  Chicago Midway-PUJ Punta Cana
22h 13m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
$551Delta
Thu, Oct 1 - Sat, Oct 17
Delta Logo
2:50 pm - 10:44 pmPUJ  Punta Cana-MDW Chicago Midway
8h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:27 pm - 12:40 pmMDW  Chicago Midway-PUJ Punta Cana
22h 13m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
$551Delta
Sat, Oct 3 - Sat, Oct 17
Delta Logo
1:07 pm - 10:44 pmPUJ  Punta Cana-MDW Chicago Midway
10h 37m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:27 pm - 12:40 pmMDW  Chicago Midway-PUJ Punta Cana
22h 13m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
$551Delta
Thu, Oct 22 - Thu, Oct 29
Southwest Logo
1:25 pm - 9:40 pmPUJ  Punta Cana-MDW Chicago Midway
9h 15m1 stop Orlando
Southwest Logo
8:55 pm - 1:45 pmMDW  Chicago Midway-PUJ Punta Cana
15h 50m2 stops Baltimore/Washington Orlando
$569Southwest
Thu, Oct 29 - Fri, Nov 6
Southwest Logo
1:25 pm - 8:20 pmPUJ  Punta Cana-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
5:05 am - 3:10 pmMDW  Chicago Midway-PUJ Punta Cana
8h 05m1 stop Baltimore/Washington
$603Southwest
Booking Insights

Price, demand and travel trends for Punta Cana to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Punta Cana to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Punta Cana to Chicago Midway Airport?

Round-trip flights from Punta Cana to Chicago Midway Airport start at $427. Prices are typical for this route right now, with typical round-trip fares ranging from $353 to $525. The lowest price found in the past 5 days was $427 on Delta.

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Expert advice

Expert advice for your flight from Punta Cana to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Mark Chesnut

Mark Chesnut

Expert on PUJ

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

Key details for Punta Cana to Chicago Midway Airport flights

Cheapest flight

$235
Flight from Punta Cana to Chicago Midway Airport

When to book flights from Punta Cana to Midway

Are your dates flexible? Find out the best times to travel from Punta Cana to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Punta Cana to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • What airlines are available from Punta Cana to Chicago Midway Airport?

    Only Southwest operates flights between Punta Cana and Chicago Midway Airport.

  • Which airports can I use when flying from Punta Cana to Chicago Midway Airport?

    Flights from Punta Cana to Chicago Midway Airport usually depart from Punta Cana (PUJ) and arrive at Chicago Midway (MDW).

  • Which airlines include bags at no extra cost on Punta Cana to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Punta Cana to Chicago Midway Airport?

    Only Economy Class is available on flights from Punta Cana to Chicago Midway Airport.

  • What is the standard checked-bag allowance on flights from Punta Cana to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$45 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Punta Cana to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by United Airlines and Southwest. Other aircraft seen on the route include Airbus A321neo variants.

  • Which airports do connecting flights from Punta Cana to Chicago Midway Airport pass through?

    One-stop flights from Punta Cana to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 33% of one-stop connections
    • Baltimore/Washington (BWI) - 33% of one-stop connections
    • Orlando (MCO) - 33% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • What are the earliest and latest flights from Punta Cana to Chicago Midway Airport?

    These are the earliest and latest flight times available from Punta Cana to Chicago Midway Airport:

    • Earliest: departs at 4:10 pm and lands at 9:15 pm
    • Latest: departs at 4:10 pm and lands at 9:15 pm.

    The flight takes about 5h 05m.

  • How long is a flight from Punta Cana to Chicago Midway Airport?

    A nonstop flight from Punta Cana to Chicago Midway Airport takes 5h 05m, covering 1,967 miles.

  • Do I need a passport to fly from Punta Cana to Chicago Midway Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How are flight prices from Punta Cana to Chicago Midway Airport looking right now?

    One-way fares from Punta Cana to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $236, which is 31% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Punta Cana to Chicago Midway Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 6h 45m, compared with 7h 27m via Orlando (MCO) and 7h 49m via Baltimore/Washington (BWI).

  • What is the time difference between Punta Cana and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Punta Cana (Central Time vs Atlantic Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

Your guide to booking Punta Cana to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

Prefer to fly direct from Punta Cana to Chicago Midway Airport?

 
Find which airlines fly direct from Punta Cana Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Punta Cana to Chicago Midway

Saturday

Southwest

Southwest

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Direct returns

Chicago Midway to Punta Cana

Saturday

Southwest

Southwest

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More options for your flight from Punta Cana to Midway

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