$57 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.

Sun, May 11 - Thu, May 15
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$196 Roundtrip, found 14 hours ago
$196
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sun, May 11 from O'Hare Intl. to Southwest Florida Intl., returning Thu, May 15, priced at $196 found 14 hours ago
Fri, May 9 - Tue, May 13
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$372 Roundtrip, found 23 hours ago
$372
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Fri, May 9 from Midway Intl. to Southwest Florida Intl., returning Tue, May 13, priced at $372 found 23 hours ago

Airfares from $57 One Way, $115 Round Trip from Chicago to Naples

Prices starting at $115 for return flights and $57 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.

Thu, May 29 - Mon, Jun 2
ORD
Chicago
RSW
Fort Myers
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Chicago to Fort Myers, returning Mon, Jun 2, priced at $115 just found
Tue, Jul 15 - Sat, Jul 19
ORD
Chicago
RSW
Fort Myers
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Jul 15 from Chicago to Fort Myers, returning Sat, Jul 19, priced at $177 found 9 hours ago
Sat, Jul 5 - Thu, Jul 10
ORD
Chicago
RSW
Fort Myers
$187 Roundtrip, found 11 hours ago
$187
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Sat, Jul 5 from Chicago to Fort Myers, returning Thu, Jul 10, priced at $187 found 11 hours ago
Tue, Dec 16 - Thu, Dec 25
ORD
Chicago
RSW
Fort Myers
$211 Roundtrip, found 12 hours ago
$211
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Dec 16 from Chicago to Fort Myers, returning Thu, Dec 25, priced at $211 found 12 hours ago
Sat, Jun 7 - Sat, Jun 14
MDW
Chicago
RSW
Fort Myers
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jun 7 from Chicago to Fort Myers, returning Sat, Jun 14, priced at $217 found 2 days ago

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
Woodspring Suites Fort Myers - Cape Coral
2.5-star property

Woodspring Suites Fort Myers - Cape Coral

7.2/10 Good! (95 reviews)

Jun 12 - Jun 16

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
The property was clean and relatively quiet. There were usually folks smoking outside but I generally felt safe. Front desk attendant only during the day--none in the evening or night.

Reviewed on Feb 11, 2025

Hyatt Place Coconut Point
3.5-star property

Hyatt Place Coconut Point

9/10 Wonderful! (1,001 reviews)

Jun 12 - Jun 16

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
Place was excellent, only thing was that housekeeping started knocking our door around 9:30am when check out was at Noon.

Reviewed on Sep 1, 2024

Sanibel Island Beach Resort
3.0-star property

Sanibel Island Beach Resort

8.8/10 Excellent! (1,075 reviews)

Jun 5 - Jun 9

4 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 20 hours ago
Great location and fabulous staff

Reviewed on Jan 29, 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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Naples

Great Deals on Flights From Chicago to Naples

Spend more of your time and money at Naples instead of sitting at your computer, searching for discount Chicago to Naples flights. This is why Orbitz makes it easy for you to check out destinations, plan your trip, and book your air fare, hotel, car rental, and more in just one place. Our low price guarantee means that you get great deals on flights from Chicago to Naples.

Flights That Fit Your Budget

Traveling on a budget? Not to worry if you are using Orbitz. We monitor thousands of fares to make sure we show you the best air ticket prices available for your travel dates. Besides amazing prices on Chicago to Naples flights, we offer you great deals on hotels, vacation packages, and last-minute getaways for the perfect trip.

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Search for Flights from Chicago to Naples on the Go

Orbitz offers free mobile apps for iPad, iPhone, and Android-based devices, so even the busiest trip-planner can research and book flights from Chicago to Naples. Find cheap Chicago to Naples flights, research local festivities and attractions, and book reservations while sitting in the salon. Orbitz will also update you on flight delays with free alerts sent to your mobile phone or email address, so you’re never left in the dark.

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.