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 | $255 (CheapOair) |
One-way from | $117 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $548 |
Good round-trip deal | $355 or less |
Good one-way deal | $167 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 2/2
9:30 am-4:02 pm
Nonstop4h 32m
Punta Cana
Fri 2/6
5:20 pm-11:39 pm
1 stop8h 19m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 2/16
8:50 am-5:25 pm
1 stop6h 35m
Punta Cana
Thu 2/19
12:56 pm-11:43 pm
1 stop12h 47m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Wed 12/3
8:45 am-5:25 pm
1 stop6h 40m
Punta Cana
Wed 12/10
5:20 pm-11:43 pm
1 stop8h 23m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Tue 12/9
6:00 am-5:25 pm
1 stop9h 25m
Punta Cana
Tue 12/16
5:20 pm-11:43 pm
1 stop8h 23m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 12/8
9:30 am-4:02 pm
Nonstop4h 32m
Punta Cana
Mon 12/15
5:20 pm-11:43 pm
1 stop8h 23m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sun 12/7
7:52 am-2:22 pm
Nonstop4h 30m
Punta Cana
Sun 12/14
5:20 pm-11:43 pm
1 stop8h 23m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Wed 12/10
8:45 am-5:25 pm
1 stop6h 40m
Punta Cana
Sat 12/13
12:56 pm-11:43 pm
1 stop12h 47m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 1/19
9:30 am-4:02 pm
Nonstop4h 32m
Punta Cana
Mon 1/26
2:55 pm-6:08 pm
Nonstop5h 13m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 1/3
10:27 am-5:12 pm
Nonstop4h 45m
Punta Cana
Sat 1/10
5:47 am-8:57 am
Nonstop5h 10m
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 2/6
8:52 am-5:25 pm
1 stop6h 33m
Punta Cana
Fri 2/13
12:56 pm-9:35 pm
1 stop10h 39m
| 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 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 25 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, March is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $194). 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.
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 38% 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. Thursday mornings 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 Saturday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
Panama City (PTY) – chosen by Cheapflights users on 43% 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 Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 6h 50m.
Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.
Crew
Entertainment
Food
Comfort
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Food
Comfort
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Food
Comfort
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Food
Comfort
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Entertainment
Food
Comfort
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$223 | Average$436 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$233 | Average$330 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$289 | Average$349 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$331 | Average$602 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$335 | Average$640 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$337 | Average$574 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$374 | Average$758 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$450 | Average$465 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$495 | Average$741 | FlexibilityNo cancel fee | On-time63% |