For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $253 (Orbitz) |
One-way from | $117 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $617 |
Good round-trip deal | $350 or less |
Good one-way deal | $187 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 1/5
7:30 am-4:50 pm
1 stop7h 20m
Punta Cana
Sat 1/17
5:47 pm-11:46 pm
1 stop7h 59m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 1/11
9:30 am-4:02 pm
Nonstop4h 32m
Punta Cana
Thu 1/15
2:55 pm-6:08 pm
Nonstop5h 13m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 1/13
7:35 am-2:05 am
1 stop16h 30m
Punta Cana
Sat 1/17
1:46 pm-12:24 am
1 stop12h 38m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 4/12
8:40 pm-1:58 pm
1 stop16h 18m
Punta Cana
Wed 4/22
1:10 pm-9:16 pm
1 stop9h 06m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 1/13
7:00 am-4:21 pm
1 stop7h 21m
Punta Cana
Fri 1/16
6:06 pm-11:59 pm
1 stop7h 53m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 3/17
8:50 am-4:25 pm
1 stop6h 35m
Punta Cana
Tue 3/24
11:56 am-6:50 pm
1 stop7h 54m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 1/20
7:00 am-4:21 pm
1 stop7h 21m
Punta Cana
Fri 1/23
6:06 pm-11:55 pm
1 stop7h 49m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 2/8
7:01 am-4:21 pm
1 stop7h 20m
Punta Cana
Fri 2/13
6:06 pm-11:57 pm
1 stop7h 51m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 3/3
6:45 am-3:30 pm
1 stop6h 45m
Punta Cana
Tue 3/10
5:05 pm-11:56 pm
1 stop7h 51m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 4/13
7:55 pm-1:24 pm
1 stop16h 29m
Punta Cana
Thu 4/23
4:05 pm-8:34 am
1 stop17h 29m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Punta Cana, you should look to book at least 90 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $209). Flying from Chicago to Punta Cana in March is currently the most expensive (average of $299). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
One of the essential ways to save on airfare from Chicago to Punta Cana is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 37% on airfare.
Travelers seeking maximum savings on their Chicago to Punta Cana flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to PUJ are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
Panama City (PTY) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago to Punta Cana on Cheapflights.
Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $231.
Flights via Charlotte (CLT) have the shortest average one-way travel time for 1-stop routes: 6h 33m.
Flights via Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 05m.
About 15% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 133 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, TUI fly have had the lowest number of delays on this route, with just 11% of flights being delayed.
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Entertainment
Crew
Comfort
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$224 | Average$434 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$334 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$263 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$350 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$322 | Average$599 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$335 | Average$632 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$337 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$373 | Average$758 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$495 | Average$740 | FlexibilityNo cancel fee | On-time63% |