$188 Find Cheap Flights from Chicago Midway Airport to Punta Cana - Compare and Save

Among airlines operating Chicago Midway Airport to Punta Cana flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

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

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

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.

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

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $649 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $690 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Arajet and Southwest. Other aircraft seen on the route include Boeing 737 MAX 9 variants.

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

• Atlanta Hartsfield-Jackson (ATL) - 84% of one-stop connections
• Baltimore/Washington (BWI) - 8% of one-stop connections
• Orlando (MCO) - 8% of one-stop connections

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

Yes. Being flexible with your travel dates can save you up to 28% on the Chicago Midway Airport to Punta Cana route. Monday is the cheapest departure day at $554 round-trip on average, while Thursday is the most expensive at $760, a difference of $206. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Punta Cana route, 39% of flights were delayed in the past 3 months, with delays averaging 1 hour 30 minutes.

Some of the most popular sights in Punta Cana are Playa Juanillo, Catalonia Caribe Golf Club and Punta Espada Golf Course. These are among the most viewed places in Punta Cana on KAYAK.

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

• Earliest: departs at 8:40 am and lands at 1:15 pm
• Latest: departs at 8:40 am and lands at 1:15 pm.

The flight takes about 4h 35m.

Last-minute fares on this route - booked within 2 weeks of departure - run 38% above the route average of $620. Book 25 weeks before departure for the lowest fares.

A nonstop flight from Chicago Midway Airport to Punta Cana takes 4h 35m, covering 1,967 miles.

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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $410 to $3,881. That means the highest observed fare was about 9x higher than the lowest one.

One-way fares from Chicago Midway Airport to Punta Cana are currently lower than usual. Average one-way flight prices are about $191, which is 36% below the typical average for this route.

Southwest is the only airline operating Chicago Midway Airport to Punta Cana flights. 61% of its flights are on time.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Orlando (MCO) gives the shortest average 1-stop total travel time at 7h 07m, compared with 7h 38m via Baltimore/Washington (BWI) and 9h 30m via Atlanta Hartsfield-Jackson (ATL).

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

Punta Cana Airport (PUJ) hosts 5 major car rental companies, with daily rates starting from around $3 for economy cars. Top options include:
• Infinity Car Rental
• Zezgo
• Alamo
• Routes Car & Truck Rentals
• Europcar

Round-trip flights from Chicago Midway Airport to Punta Cana range from $502 to $890, with an average of $620 over the past 12 months. Anything below $502 counts as a good deal.