$26 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.

Fri, May 31 - Tue, Jun 18
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 31 from O'Hare Intl. to Southwest Florida Intl., returning Tue, Jun 18, priced at $116 just found
Fri, May 31 - Fri, May 31
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 4 days ago
$163
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, May 31 from Midway Intl. to Southwest Florida Intl., returning Fri, May 31, priced at $163 found 4 days ago

Airfares from $26 One Way, $51 Round Trip from Chicago to Naples

Prices starting at $51 for return flights and $26 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, Sep 10 - Wed, Sep 11
ORD
Chicago
RSW
Fort Myers
$51 Roundtrip, found 9 hours ago
$51
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from Chicago to Fort Myers, returning Wed, Sep 11, priced at $51 found 9 hours ago
Wed, Sep 11 - Wed, Sep 18
ORD
Chicago
RSW
Fort Myers
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Sep 11 from Chicago to Fort Myers, returning Wed, Sep 18, priced at $63 just found
Thu, Sep 5 - Wed, Sep 11
ORD
Chicago
RSW
Fort Myers
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Sep 5 from Chicago to Fort Myers, returning Wed, Sep 11, priced at $74 just found
Sat, Aug 17 - Sat, Aug 24
MDW
Chicago
RSW
Fort Myers
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 17 from Chicago to Fort Myers, returning Sat, Aug 24, priced at $160 found 4 days ago
Sat, Jun 1 - Thu, Jul 4
ORD
Chicago
RSW
Fort Myers
$163 Roundtrip, found 6 hours ago
$163
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Jun 1 from Chicago to Fort Myers, returning Thu, Jul 4, priced at $163 found 6 hours ago

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Fort Myers at Bell Tower Shops
4.0-star property

Doubletree by Hilton Fort Myers at Bell Tower Shops

8.6/10 Excellent! (1,005 reviews)

Jul 18 - Jul 21

3 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
We had a very nice two nights at the Doubletree. The pool was a little disappointing (the extreme pebble effect made it painful to walk into the pool and it could have been cleaner), but there are some great restaurants and it is in a massive shopping area, so easy to spend time during the day. All customer service was friendly and efficient. Small gym had everything needed for a workout while traveling.

Reviewed on Apr 27, 2024

LaPlaya Beach & Golf Resort - A Noble House Resort
4.5-star property

LaPlaya Beach & Golf Resort - A Noble House Resort

9/10 Wonderful! (1,009 reviews)

Jul 6 - Jul 10

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 10 hours ago
Everything was good. Everyone was nice. However, the prices on food were a little outrageous in the restaurant.

Reviewed on Jul 30, 2023

Homewood Suites by Hilton - Fort Myers
3.0-star property

Homewood Suites by Hilton - Fort Myers

9/10 Wonderful! (1,001 reviews)

Jun 27 - Jul 1

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
just found
Everything was great !

Reviewed on Jul 27, 2022

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Naples first class flight packages

Price found within the past 48 hours. Click for updated prices.
Bellasera Resort
4.0-star property

Bellasera Resort

9.6/10 Exceptional! (1,922 reviews)

Jul 5 - Jul 12

7 night stay

Chicago (ORD) to Fort Myers (RSW)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 8 hours ago
I would have liked to have a microwave in the room and I would have. I would like to have a couple more chairs in the room to sit instead of sitting on the bed. Other than that, it’s a great place. I would come back again.

Reviewed on Apr 19, 2024

LaPlaya Beach & Golf Resort - A Noble House Resort
4.5-star property

LaPlaya Beach & Golf Resort - A Noble House Resort

9/10 Wonderful! (1,009 reviews)

Jul 5 - Jul 12

7 night stay

Chicago (ORD) to Fort Myers (RSW)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 8 hours ago
Everything was good. Everyone was nice. However, the prices on food were a little outrageous in the restaurant.

Reviewed on Jul 30, 2023

Naples Grande Beach Resort
4.5-star property

Naples Grande Beach Resort

8.6/10 Excellent! (1,187 reviews)

Jul 5 - Jul 12

7 night stay

Chicago (ORD) to Fort Myers (RSW)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 8 hours ago
Clean, good service, early check in options, beautiful.

Reviewed on May 12, 2024

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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, Swiss, United Airlines, Spirit Airlines
Earliest Flight Arrival
2:26PM UTC
Latest Flight Arrival
2:15AM UTC

Chicago to Naples

It has never been easier to find cheap Chicago to Naples flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.

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Get the Best Deals on Chicago to Naples Flights

Finding great deals on flights from Chicago to Naples is a snap with Orbitz. With our guaranteed low prices, you don’t have to worry if you are getting the best prices on air tickets, hotels, and cruises. And with all that money you saved, you can enjoy your Naples vacation even more.

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Flight Alerts Keep You Informed

Stay on top of the latest updates for flights from Chicago to Naples. We send you free email and mobile alerts to keep you informed about delays to Chicago to Naples flights.

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.