
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $332 (FlightHub) |
One-way from | $152 (Trip.com) |
Popular in | March |
Cheapest in | October |
Average price | $1,125 |
Good round-trip deal | $571 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 4/13
6:00 am-1:21 pm
1 stop6h 21m
Punta Cana
Fri 4/17
2:46 pm-10:28 pm
1 stop8h 42m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 5/1
8:35 pm-2:15 pm
2 stops16h 40m
Punta Cana
Mon 5/4
2:05 pm-12:05 am
1 stop11h 00m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 5/15
9:25 pm-11:55 am
1 stop13h 30m
Punta Cana
Mon 5/18
4:00 pm-9:10 am
2 stops18h 10m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 5/2
9:40 am-3:00 pm
Nonstop4h 20m
Punta Cana
Thu 5/7
1:40 pm-10:20 pm
1 stop9h 40m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/9
5:59 pm-12:20 pm
2 stops17h 21m
Punta Cana
Fri 6/12
4:15 pm-12:30 pm
2 stops21h 15m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/26
6:00 am-2:32 pm
1 stop7h 32m
Punta Cana
Tue 5/5
3:57 pm-10:28 pm
1 stop7h 31m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 4/11
9:40 am-3:00 pm
Nonstop4h 20m
Punta Cana
Wed 4/15
2:05 pm-9:25 pm
1 stop8h 20m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 6/9
5:59 pm-12:20 pm
2 stops17h 21m
Punta Cana
Sat 6/13
5:15 pm-9:51 am
1 stop17h 36m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 6/1
9:25 pm-1:05 pm
2 stops14h 40m
Punta Cana
Mon 6/8
1:25 pm-11:00 pm
2 stops10h 35m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 5/4
6:00 am-1:21 pm
1 stop6h 21m
Punta Cana
Thu 5/7
2:50 pm-9:09 pm
1 stop7h 19m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Punta Cana (average of $252). Flying from Chicago Midway Airport to Punta Cana in December is currently the most expensive (average of $863). 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 Midway Airport to Punta Cana as you normally would.
About 24% of weekly flights between Chicago and Punta Cana have experienced delays in the past year, with the average delay time being 109 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, Southwest have had the lowest number of delays on this route, with just 24% of flights being delayed.
Baltimore (BWI) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago Midway Airport to Punta Cana on Cheapflights.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $606.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 8h 03m.
Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.
Food
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Comfort
Crew
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Anonymous,Mar 2026
KOA - HNL
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KOA - HNL
Food
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Anonymous,Mar 2026
KOA - HNL
Food
Entertainment
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Comfort
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Overall
Reviews
Anonymous,Mar 2026
KOA - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$418 | Average$659 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$539 | Average$779 | FlexibilityNo cancel fee | On-timeN/A |