
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $610 (American Airlines) |
One-way from | $360 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $694 |
Good round-trip deal | $1,045 or less |
Good one-way deal | $663 or less |
Fly from
Fly to
Route
Depart
Return
NaplesChicago
NAP - ORD
NAPORD
Naples
Thu 9/3
6:35 am-1:10 pm
1 stop13h 35m
Chicago O'Hare Intl
Sun 9/6
3:00 pm-10:40 pm
1 stop24h 40m
NaplesChicago
NAP - ORD
NAPORD
Naples
Thu 10/15
3:00 pm-6:50 pm
Nonstop10h 50m
Chicago O'Hare Intl
Mon 10/19
5:25 pm-10:00 am
Nonstop9h 35m
NaplesChicago
NAP - ORD
NAPORD
Naples
Mon 7/6
3:00 pm-6:45 pm
Nonstop10h 45m
Chicago O'Hare Intl
Fri 7/17
7:05 pm-10:00 pm
1 stop19h 55m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 7/14
3:00 pm-6:45 pm
Nonstop10h 45m
Chicago O'Hare Intl
Sat 8/1
7:05 pm-10:00 pm
1 stop19h 55m
NaplesChicago
NAP - ORD
NAPORD
Naples
Fri 6/26
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Tue 6/30
9:15 pm-10:00 pm
1 stop17h 45m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 7/14
3:00 pm-6:45 pm
Nonstop10h 45m
Chicago O'Hare Intl
Fri 7/31
9:15 pm-10:00 pm
1 stop17h 45m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 7/21
12:00 pm-7:26 pm
1 stop14h 26m
Chicago O'Hare Intl
Tue 7/28
7:05 pm-6:05 pm
1 stop16h 00m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 7/21
12:00 pm-7:26 pm
1 stop14h 26m
Chicago O'Hare Intl
Tue 8/11
10:30 pm-6:05 pm
1 stop12h 35m
NaplesChicago
NAP - ORD
NAPORD
Naples
Tue 7/14
12:00 pm-3:33 pm
1 stop34h 33m
Chicago O'Hare Intl
Sun 8/2
5:00 pm-1:55 pm
1 stop13h 55m
NaplesChicago
NAP - ORD
NAPORD
Naples
Thu 6/25
3:00 pm-6:55 pm
Nonstop10h 55m
Chicago O'Hare Intl
Sun 7/12
5:30 pm-10:00 am
Nonstop9h 30m
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.
When flying from Naples to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
The most flights from NAP to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
About 21% 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 21% of flights being delayed.
Entertainment
Food
Crew
Comfort
Overall
Boarding
Reviews
Muhammad,Jan 2026
ORD - DFW
Entertainment
Food
Crew
Comfort
Overall
Boarding
Reviews
Muhammad,Jan 2026
ORD - DFW