Find a great deal and save up to 8% by booking at least 36 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago Midway Airport to Naples within the next two weeks, with the cheapest ticket starting at $662.
Flights from Chicago Midway Airport to Naples lean towards being more expensive in June. Prices are generally better when you fly from Chicago Midway Airport to Naples in February, with the cheapest ticket starting at $474.
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 Naples as you normally would.
Fly from
Fly to
Budget
$764 - $1,922
Route
Depart
Return
Price
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Mon 7/22
2 stops18h 30m
Naples
Wed 10/9
2 stops17h 48m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Sun 8/18
2 stops15h 11m
Naples
Tue 8/27
2 stops22h 11m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Wed 9/25
2 stops17h 30m
Naples
Fri 10/4
2 stops19h 09m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Mon 8/19
2 stops18h 30m
Naples
Mon 8/26
2 stops22h 11m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Wed 8/21
2 stops25h 31m
Naples
Mon 9/2
2 stops37h 00m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Mon 10/21
2 stops14h 35m
Naples
Mon 10/28
2 stops16h 53m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Tue 7/16
2 stops18h 30m
Naples
Tue 7/23
2 stops17h 43m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Sat 10/19
2 stops14h 19m
Naples
Sun 10/27
2 stops17h 55m
Chicago MidwayNaples
MDW - NAP
MDWNAP
Chicago Midway
Tue 7/23
3 stops18h 05m
Naples
Fri 7/26
3 stops29h 57m
No data available for this route at this time. Please check back soon.
Entertainment
Overall
Boarding
Comfort
Food
Crew
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.
Entertainment
Overall
Boarding
Comfort
Food
Crew
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.
Entertainment
Overall
Boarding
Comfort
Food
Crew
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.
Entertainment
Overall
Boarding
Comfort
Food
Crew
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.