$293+ Cheap flights from Chicago (CHI) to Naples (NAP)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Naples with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Naples are usually found in January or March, booked 79 days in advance, depart on a Tuesday or Monday and return on a Monday
Cheap flight deals from Chicago to Naples
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Naples (NAP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.
Round-trip from | $761 (Air Canada) |
|---|---|
One-way from | $293 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $1,221 |
Good round-trip deal | $712 or less |
Good one-way deal | $686 or less |
Find flight deals from Chicago to Naples
Cheapest flights from Chicago to NaplesExplore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Chicago to Naples. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This FlightHub deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Iberia deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This SWISS deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This KLM deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Gotogate deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air France deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This KLM deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Naples that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Chicago to Naples that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/3
2:00 pm-2:20 pm
2 stops17h 20m
Naples
Tue 8/19
6:35 am-9:36 pm
2 stops22h 01m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/3
4:30 pm-10:05 pm
1 stop22h 35m
Naples
Tue 8/19
10:05 am-10:49 pm
2 stops19h 44m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Wed 7/16
7:05 pm-2:00 pm
1 stop11h 55m
Naples
Wed 7/23
7:15 pm-12:10 pm
1 stop23h 55m
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Sat 8/16
6:04 am-7:00 am
1 stop17h 56m
Naples
Sat 8/23
6:10 am-5:37 pm
2 stops18h 27m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/3
10:35 am-7:00 am
1 stop13h 25m
Naples
Tue 8/19
6:40 am-3:04 pm
2 stops15h 24m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sat 8/23
8:35 pm-1:00 pm
Nonstop9h 25m
Naples
Sat 8/30
3:00 pm-6:50 pm
Nonstop10h 50m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Sun 8/3
7:25 pm-6:50 pm
2 stops16h 25m
Naples
Tue 8/19
11:20 am-9:15 pm
2 stops16h 55m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Mon 8/4
3:45 pm-10:40 am
1 stop11h 55m
Naples
Thu 8/14
11:40 am-7:00 pm
1 stop14h 20m
ChicagoNaples
MDW - NAP
MDWNAP
Chicago Midway
Sat 8/16
10:11 am-7:00 am
1 stop13h 49m
Naples
Sat 8/23
9:00 am-9:12 pm
1 stop19h 12m
ChicagoNaples
ORD - NAP
ORDNAP
Chicago O'Hare Intl
Fri 8/29
6:25 pm-10:55 pm
2 stops21h 30m
Naples
Sun 9/7
6:40 am-2:55 pm
1 stop15h 15m
Best time to book a flight from Chicago to Naples
Have a flexible travel schedule? Discover the best time to fly to Naples from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Naples
How far ahead should I book a flight from Chicago to Naples?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Naples. Price data was last updated on June 9, 2025.
The price you pay for your flight from Chicago to Naples may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Naples?
Currently, January is the cheapest month in which you can book a flight from Chicago to Naples (average of $703). Flying from Chicago to Naples in June is currently the most expensive (average of $1,217). 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.
What is the cheapest time of day to fly from CHI to NAP?
Find hourly flight availability from Chicago to Naples. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
A simple way to save on the total cost of your ticket is to fly from Chicago to Naples in the morning. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Chicago to Naples?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Naples. Price data was last updated on June 30, 2024.
Travelers seeking maximum savings on their Chicago to Naples flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Naples
Explore weekly flight availability from Chicago to Naples. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.
The most flights from CHI to NAP are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
Rainfall in Naples by month
Plan your trip to Naples by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Naples ranges from 0.9 - 6.4 inches per month. November is typically the wettest month, when rainfall can reach 6.4 in. July is typically the driest time to visit Naples when rainfall is around 0.9 in.
Temperature in Naples by month
Plan your trip to Naples by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Naples, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).
Reviews of airlines servicing Naples
Get insights into the airlines that provide service to Naples. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Naples. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Austrian Airlines from Chicago to Naples to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Boarding
Comfort
Food
Overall
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Chicago to Naples. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Naples
See prices for flight routes from nearby airports that may be better suited for you.
Top 9 airlines flying from Chicago to Naples
Discover the top 9 airlines that operate flights from Chicago to Naples. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$497 | Average$763 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$536 | Average$626 | FlexibilityNo cancel fee | On-time77% | |
| Cheapest$581 | Average$917 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$594 | Average$944 | FlexibilityNo cancel fee | On-time76% | |
| Cheapest$602 | Average$1,081 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$627 | Average$1,065 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$640 | Average$1,202 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$679 | Average$1,000 | FlexibilityNo cancel fee | On-time81% | |
| Cheapest$686 | Average$910 | FlexibilityNo cancel fee | On-timeN/A |