Cheap flights from Naples to Chicago from $431
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Naples to Chicago departing on 10/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Naples to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap direct flights
American Airlines flights from Naples to Chicago
Our best American Airlines deals on Naples to Chicago flight tickets
United Airlines flights from Naples to Chicago
Our best United Airlines deals on Naples to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Naples to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $632. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Naples to Chicago for around $999.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Naples to Chicago during this time can be as low as $709. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $947.
What is the cheapest Naples to Chicago flight route?
Fly from Naples to Chicago O'Hare Intl for the best Naples - Chicago flight prices
What cabin class options are available on Naples to Chicago flights?
There are 3 cabin classes available to choose from on Naples to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Naples to Chicago on average per day?
1 flights are operational daily from Naples to Chicago as of June 2025. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.
How many flights depart from Naples to Chicago on average per week?
As of June 2025, there are 7 flights per week flying from Naples to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Naples to Chicago
Cheap Naples to Chicago (NAP to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Naples to Chicago
How far is Naples to Chicago by plane?
The straight-line distance from Naples to Chicago is 4923.3 mi. Typically, this will take 10h 40m by plane in normal conditions.
When did momondo last update prices for flights from Naples Airport to Chicago?
Prices for flights from Naples Airport to Chicago were last updated today.
How many operators does momondo search for flights from Naples Airport to Chicago?
As of June 2025, there is 1 operator available to choose from for flights from Naples Airport to Chicago.
How old do you have to be to fly from Naples Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Naples Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Naples to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Naples to Chicago is Boeing 787-9 Dreamliner (31.86% of total bookings). The next most popular plane models are Boeing 787-8 Dreamliner (26.55%), Airbus A330-300 (8.85%), and Airbus A330-900neo (7.08%).
Best airlines flying from Naples to Chicago
Compare and see reviews for airlines that fly from Naples to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $664 | Free Cancellation | Rating 7.2 10,000 reviews |
American Airlines Flights From Naples to Chicago
American Airlines flies from Naples to Chicago around 7 times per week, with 10,000 momondo users rating the airline 7.2/10. The cheapest American Airlines deal from Naples to Chicago in the last 72 hours was $664 (round-trip), much lower than the average airfare cost of $919 for American Airlines flights on this route.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Naples to Chicago?
It is quick and easy to find Naples to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Naples to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Naples to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Naples to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Naples to Chicago.
I’m not ready to book a flight from Naples to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Naples. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.