When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 36 days in advance, which can save you up to 8% on flights from Illinois to Naples compared to booking the week you need them. Waiting 36 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $662. For sooner than that we have options available in the next 3 days from $1,993.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, February can be a great choice for travel to Naples. Flights to Naples from Illinois in February are about $982 on average during February, but can be found for as low as $474.
When flying from Illinois to Naples, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$629 - $946
Route
Depart
Return
Price
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Tue 9/24
1 stop29h 00m
Naples
Mon 10/7
1 stop29h 10m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/18
1 stop12h 35m
Naples
Tue 8/27
1 stop13h 35m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/18
1 stop20h 45m
Naples
Wed 8/28
2 stops18h 41m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Sun 8/18
2 stops15h 25m
Naples
Tue 8/27
2 stops22h 12m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Tue 9/24
1 stop18h 35m
Naples
Mon 10/7
2 stops30h 25m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 9/15
1 stop17h 20m
Naples
Sat 9/21
1 stop28h 00m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Fri 9/20
2 stops15h 50m
Naples
Sat 9/28
1 stop12h 55m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Fri 6/28
2 stops45h 47m
Naples
Sun 7/7
1 stop21h 05m
Chicago O'Hare IntlNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 9/1
2 stops25h 20m
Naples
Wed 9/11
2 stops21h 25m
No data available for this route at this time. Please check back soon.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Crew
Boarding
Food
Overall
Entertainment
Comfort
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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