$50 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.

Sat, Jun 21 - Sat, Jun 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$303 Roundtrip, just found
$303
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jun 28, priced at $303 just found
Sun, Jun 22 - Sun, Jun 29
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$397 Roundtrip, found 1 day ago
$397
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jun 22 from Midway Intl. to Southwest Florida Intl., returning Sun, Jun 29, priced at $397 found 1 day ago

Airfares from $50 One Way, $100 Round Trip from Chicago to Naples

Prices starting at $100 for return flights and $50 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.

Sat, Aug 16 - Wed, Aug 20
ORD
Chicago
RSW
Fort Myers
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Chicago to Fort Myers, returning Wed, Aug 20, priced at $100 found 2 hours ago
Mon, Aug 4 - Thu, Aug 14
ORD
Chicago
RSW
Fort Myers
$120 Roundtrip, found 3 hours ago
$120
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Mon, Aug 4 from Chicago to Fort Myers, returning Thu, Aug 14, priced at $120 found 3 hours ago
Sun, Aug 10 - Thu, Aug 14
MDW
Chicago
RSW
Fort Myers
$162 Roundtrip, found 9 hours ago
$162
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sun, Aug 10 from Chicago to Fort Myers, returning Thu, Aug 14, priced at $162 found 9 hours ago
Fri, Dec 12 - Mon, Dec 15
ORD
Chicago
RSW
Fort Myers
$211 Roundtrip, found 6 hours ago
$211
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Fri, Dec 12 from Chicago to Fort Myers, returning Mon, Dec 15, priced at $211 found 6 hours ago
Thu, Oct 9 - Sun, Oct 12
MDW
Chicago
RSW
Fort Myers
$224 Roundtrip, found 6 days ago
$224
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Oct 9 from Chicago to Fort Myers, returning Sun, Oct 12, priced at $224 found 6 days ago

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers
3.0-star property

Hilton Garden Inn Ft Myers

8.6/10 Excellent! (1,002 reviews)

Jul 31 - Aug 3

3 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
I had a wonderful time at the Hilton Garden Inn in Fort Myers Florida. I would like to thank every member of staff for their hospitality. Loved the dinner options at the restaurant. A special to Patrick for getting me around on a very a short notice. I would love to see the company purchase a golf cart for people with mobility issues.

Reviewed on Aug 22, 2024

Bellasera Resort
4.0-star property

Bellasera Resort

9.6/10 Exceptional! (2,174 reviews)

Aug 5 - Aug 9

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Coach

Fort Myers (RSW) to Chicago (ORD)

United • Coach
Save 100% on your flight
per person
found 14 hours ago
I love staying at Bella. It’s like an oasis away from the hustle and bustle but a short distance from all the shopping you could even walk if you wanted to and a short distance from the beach, Bella Sarah provides transportation so you don’t have to worry about parking and also the beach chairs and umbrella and towels, this is a wonderful beautiful property with very thoughtful amenities

Reviewed on Jul 8, 2024

Edison Beach House
3.5-star property

Edison Beach House

9.4/10 Exceptional! (1,365 reviews)

Jul 31 - Aug 3

3 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Easy check in. Friendly staff. Great location. Room was wonderful. Would come back again!

Reviewed on May 24, 2025

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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Naples

Using Orbitz can save you a significant amount of money and time when booking Chicago to Naples flights. With cutting-edge mobile tools for on-the-move travel planning and guaranteed low prices, Orbitz is the ultimate resource for travelers looking for great deals.

Book Your Chicago to Naples Flights From Any Location

Orbitz now offers free apps for iPad, iPhone, and Android users. You can use Orbitz on these devices to search for affordable fares and to book flights from Chicago to Naples. Mobile apps also allow users to view, compare, and book hotel rooms with just a few taps on the screen and let you access up-to-date flight and baggage claim information in a matter of seconds.

Fly Cheap and Boost Your Frequent Flyer Miles

Earn miles or points on select Chicago to Naples flights to boost your frequent flyer travel rewards. When using Orbitz to book domestic or international flights, include your frequent flyer numbers or add these details to your Orbitz user profile so they are included with your reservation.

Keep Everyone Updated With Flight Alerts

Orbitz is the ideal way to book flights from Chicago to Naples. Free Orbitz alerts can be sent to you and as many as six of your contacts about changes to your Chicago to Naples flights. This keeps everyone notified of flight delays or any other disruptions that might impact your arrival time.

Orbitz Makes It Easy to Plan Your Trips on a Budget

You can always find affordable flights from Chicago to Naples on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

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.