$36 Cheap flight deals from Chicago (CHI) to Naples (APF)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Naples

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $36 One Way, $71 Round Trip from Chicago to Naples

Prices starting at $71 for return flights and $36 for one-way flights to Naples were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
Inn on Fifth
LaPlaya Beach & Golf Resort - A Noble House Resort
Naples Grande Beach Resort
Don't see what you're looking for?
See all available trips from Chicago to Naples
View all trips

More About Flying To Naples from Chicago

Route Information for Flights from Chicago to Naples

Origin Airport IATA Code
CHI
Destination Airport IATA Code
APF
Distance
1122 mi
Direct Flight Airlines
American Airlines, Alaska Airlines, Air Canada, Swiss, United Airlines, Spirit Airlines
Earliest Flight Arrival
3:17PM UTC
Latest Flight Arrival
2:15AM UTC

Chicago to Naples

When you’re ready to take your next trip, get the most affordable prices on flights from Chicago to Naples with Orbitz! The guaranteed low prices and cutting-edge mobile tools on Orbits make it easy for you to plan your next great vacation.

Keep Up With Sudden Flight Changes

As any traveler knows, air travel can suddenly be temporarily halted due to service disruptions. Along with offering the best fares for flights from Chicago to Naples, Orbitz also offers free mobile phone and email alerts that help you keep up with sudden changes to your flight plans. Choose from email, text, or voice message alerts.

Get Great Prices for Chicago to Naples Flights

Orbitz features both an Android app and an iPhone app to give you the lowest prices for Chicago to Naples flights. Use these mobile apps to get updates on your flight, the details of your itinerary, and to learn about available hotel deals in the area.

Fly for Less and Earn Miles

Did you know you can earn miles and points for your frequent flyer program with Orbitz? To do this with specific flights from Chicago to Naples, enter your frequent flyer account number when you book your ticket online. For even more convenience, keep a record of your loyalty travel program numbers directly with Orbitz by storing them in your account profile. This way, you can add your account numbers to your next reservation for Chicago to Naples flights automatically without the annoying hassle of having to look them up.

Frequently asked questions

Are there non-stop flights from Chicago to Naples?
There definitely are, so you’ll only have to make a note of one flight number. Pick from 4 airlines that run nonstop services from O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport, including:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Southwest Airlines

What is the shortest flight from Chicago to Naples?
It can take as little as 2 hours and 44 minutes to travel from Chicago, IL (ORD-O’Hare Intl.) to RSW. Settle in and enjoy the journey, because you’ll be walking through arrivals before long.
What airlines fly from Chicago to Naples most frequently?
Satisfy your wanderlust and jet off with one of the following airlines that offer the most frequent flights from Chicago to Naples: United Airlines - (UA) with 117 flights every month American Airlines - (AA) with 47 flights every month Spirit Airlines - (NK) with 30 flights every month Southwest Airlines - (WN) with 8 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.