$50 Cheap flight deals from Chicago (CHI) to Naples (APF)

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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 - Mon, Jun 23
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$344 Roundtrip, found 1 hour ago
$344
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jun 23, priced at $344 found 1 hour ago
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.

Tue, Aug 19 - Sat, Aug 23
ORD
Chicago
RSW
Fort Myers
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Fort Myers, returning Sat, Aug 23, priced at $100 just found
Sat, Jul 5 - Fri, Jul 11
ORD
Chicago
RSW
Fort Myers
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jul 5 from Chicago to Fort Myers, returning Fri, Jul 11, priced at $109 just found
Tue, Aug 12 - Thu, Aug 14
MDW
Chicago
RSW
Fort Myers
$162 Roundtrip, found 3 hours ago
$162
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Fort Myers, returning Thu, Aug 14, priced at $162 found 3 hours ago
Wed, Dec 3 - Sun, Dec 7
ORD
Chicago
RSW
Fort Myers
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Dec 3 from Chicago to Fort Myers, returning Sun, Dec 7, priced at $211 found 1 hour 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 21 - Jul 25

4 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
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

Lani Kai Beachfront Resort
3.5-star property

Lani Kai Beachfront Resort

8.6/10 Excellent! (1,025 reviews)

Jul 29 - Aug 5

7 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Coach

Fort Myers (RSW) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Staff was friendly at check in but when it was 11:04am we got a rude call saying we need to leave the room right now. It just could’ve been addressed nicer. It was 4 mins past and we were zipping up our suitcases. The remodeled rooms are really nice and the sliding glass door was great at keeping noise out. This resort holds a special place in my heart from trips as a kid and it was great to revisit it. Drink prices were affordable and the overall vibe was friendly and fun. Food and shopping was also very enjoyable

Reviewed on May 10, 2025

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 20 hours ago
Easy check in. Friendly staff. Great location. Room was wonderful. Would come back again!

Reviewed on May 24, 2025

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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, Air New Zealand, Swiss, United Airlines, Spirit Airlines
Earliest Flight Arrival
2:42PM UTC
Latest Flight Arrival
12:17AM UTC

Chicago to Naples

Getting a spectacularly low fare on Chicago to Naples flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Chicago to Naples, discount hotel accommodations, cheap car rentals, and more.

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Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Chicago to Naples. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

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Build up points or miles for your frequent flyer plan with qualifying Chicago to Naples flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

Flight Alerts Take the Hassle out of Travel

You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Chicago to Naples. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Chicago to Naplesare always found on Orbitz.

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.