
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Cheapflightsfares) |
One-way from | $116 (Cheapflightsfares) |
Popular in | March |
Cheapest in | August |
Average price | $469 |
Good round-trip deal | $380 or less |
Good one-way deal | $165 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 5/15
6:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Thu 5/21
7:30 pm-11:40 pm
Nonstop5h 10m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 4/25
3:52 pm-12:09 pm
2 stops43h 17m
Punta Cana
Sat 5/2
2:56 pm-10:39 pm
1 stop8h 43m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 4/11
7:17 am-3:56 pm
1 stop7h 39m
Punta Cana
Wed 4/15
4:47 pm-9:12 am
2 stops17h 25m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 4/7
7:20 pm-1:05 pm
1 stop16h 45m
Punta Cana
Tue 4/14
3:57 pm-10:28 pm
1 stop7h 31m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 4/11
8:45 am-2:27 pm
Nonstop4h 42m
Punta Cana
Wed 4/15
1:50 pm-5:59 pm
Nonstop5h 09m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 4/13
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
Fri 4/17
3:57 pm-10:28 pm
1 stop7h 31m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/26
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
Wed 4/29
3:57 pm-10:28 pm
1 stop7h 31m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/12
6:00 am-2:25 pm
1 stop7h 25m
Punta Cana
Thu 4/16
1:00 pm-10:28 pm
1 stop10h 28m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 5/17
7:35 pm-3:00 pm
2 stops18h 25m
Punta Cana
Thu 5/21
1:40 pm-9:45 am
2 stops21h 05m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 5/17
8:50 pm-3:00 pm
2 stops17h 10m
Punta Cana
Thu 5/21
1:40 pm-10:20 pm
1 stop9h 40m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
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, December is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $195). Flying from Chicago to Punta Cana in October is currently the most expensive (average of $289). 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.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Punta Cana as you normally would.
The most flights from CHI to PUJ are scheduled on a Saturday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
Panama City (PTY) – chosen by Cheapflights users on 33% of 1-stop itineraries from Chicago to Punta Cana on Cheapflights.
Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $378.
Flights via Charlotte (CLT) have the shortest average one-way travel time for 1-stop routes: 6h 33m.
Flights via Panama City (PTY) offer the fastest connection on this route, with an average layover time of 0h 45m.
About 17% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 135 minutes.
Historically, flights departing at night 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 Saturday 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
Overall
Comfort
Crew
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Overall
Comfort
Crew
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Overall
Comfort
Crew
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Overall
Comfort
Crew
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Boarding
Food
Overall
Comfort
Crew
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$181 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$614 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$223 | Average$431 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$229 | Average$344 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$245 | Average$629 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$260 | Average$428 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$277 | Average$655 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$334 | Average$589 | FlexibilityNo cancel fee | On-time69% |