$180 Find Cheap Flights from Punta Cana to Chicago - Compare and Save

Among airlines operating Punta Cana to Chicago flights:

• United Airlines: offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection
• JetBlue: offers extra legroom; offers free seat selection

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

4 airlines operate flights between Punta Cana and Chicago. The airlines offering nonstop flights on this route include:

• American Airlines
• United Airlines
• Arajet
• Southwest

Flights from Punta Cana to Chicago usually depart from Punta Cana (PUJ) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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

• American Airlines: a cabin bag and a checked bag in Economy Class
• WorldTicket: a cabin bag and a checked bag in Economy Class
• Hahn Air: a cabin bag and a checked bag in Economy Class

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

Two cabin classes are available on flights from Punta Cana to Chicago:

• Economy Class
• Business Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $256 round-trip via Fort Lauderdale (FLL), compared to $508 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $25–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

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

• Charlotte Douglas (CLT) - 36% of one-stop connections
• Fort Lauderdale (FLL) - 21% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 7% of one-stop connections
• Baltimore/Washington (BWI) - 7% of one-stop connections

Charlotte Douglas (CLT) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 31% on the Punta Cana to Chicago route. Thursday is the cheapest departure day at $436 round-trip on average, while Monday is the most expensive at $629, a difference of $193. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Afternoon is the busiest departure period on Punta Cana to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

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

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

• Earliest: departs at 5:47 am and lands at 11:06 am
• Latest: departs at 7:30 pm and lands at 12:49 am.

The flight takes about 5h 19m.

Last-minute fares on this route - booked within 2 weeks of departure - run 45% above the route average of $482. Book 16 weeks before departure for the lowest fares.

A nonstop flight from Punta Cana to Chicago takes 5h 19m, 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 $289 to $2,250. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Punta Cana to Chicago are currently lower than usual. Average one-way flight prices are about $202, which is 32% below the typical average for this route.

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 Charlotte Douglas (CLT).

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

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Punta Cana to Chicago range from $368 to $658, with an average of $482 over the past 12 months. Anything below $368 counts as a good deal.

American Airlines is the only airline on the Punta Cana to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.