
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $570 (lol.travel) |
One-way from | $374 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $675 |
Good one-way deal | $591 or less |
Fly from
Fly to
Route
Depart
Return
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Mon 5/25
5:30 pm-10:00 am
Nonstop9h 30m
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Mon 5/25
5:30 pm-10:00 am
Nonstop9h 30m
NaplesChicago
NAP - MDW
NAPMDW
Naples
Fri 6/12
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
6:05 am-8:10 am
2 stops19h 05m
NaplesChicago
NAP - ORD
NAPORD
Naples
Fri 6/12
6:05 am-3:10 pm
1 stop16h 05m
Chicago O'Hare Intl
Tue 6/16
9:48 am-7:05 am
1 stop14h 17m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 6/9
10:15 am-9:48 pm
1 stop18h 33m
Chicago O'Hare Intl
Tue 6/16
6:05 am-8:10 am
1 stop19h 05m
NaplesChicago
NAP - MDW
NAPMDW
Naples
Tue 6/9
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
6:05 am-8:10 am
2 stops19h 05m
NaplesChicago
NAP - MDW
NAPMDW
Naples
Fri 6/12
6:05 am-6:31 pm
2 stops19h 26m
Chicago Midway
Tue 6/16
11:05 am-7:05 am
1 stop13h 00m
NaplesChicago
NAP - ORD
NAPORD
Naples
Fri 6/12
6:05 am-6:29 pm
2 stops19h 24m
Chicago O'Hare Intl
Tue 6/16
9:48 am-7:05 am
1 stop14h 17m
NaplesChicago
NAP - ORD
NAPORD
Naples
Sat 5/23
12:45 pm-2:15 pm
1 stop32h 30m
Chicago O'Hare Intl
Fri 5/29
6:06 pm-7:05 am
1 stop29h 59m
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 5/18
7:40 am-6:15 pm
1 stop17h 35m
Chicago O'Hare Intl
Mon 5/25
7:05 pm-10:00 pm
1 stop19h 55m
Currently, November is the cheapest month in which you can book a flight from Naples to Chicago (average of $481). Flying from Naples to Chicago in March is currently the most expensive (average of $728). 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.
About 23% of weekly flights between Naples and Chicago have experienced delays in the past year, with the average delay time being 222 minutes.
Historically, flights departing in the early afternoon 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 Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, American Airlines have had the lowest number of delays on this route, with just 23% of flights being delayed.
Boarding
Comfort
Food
Overall
Crew
Entertainment
Reviews
Muhammad,Jan 2026
ORD - DFW
Boarding
Comfort
Food
Overall
Crew
Entertainment
Reviews
Muhammad,Jan 2026
ORD - DFW
Boarding
Comfort
Food
Overall
Crew
Entertainment
Reviews
Muhammad,Jan 2026
ORD - DFW
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$639 | Average$738 | FlexibilityNo cancel fee | On-time71% |