$45 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, Apr 26 - Sat, May 2
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Southwest Florida Intl., returning Sat, May 2, priced at $113 found 1 hour ago
Fri, Apr 24 - Sun, Apr 26
RFD
Greater Rockford
RSW
Southwest Florida Intl.
$438 Roundtrip, found 5 hours ago
$438
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Apr 24 from Greater Rockford to Southwest Florida Intl., returning Sun, Apr 26, priced at $438 found 5 hours ago
Fri, Apr 24 - Sun, Apr 26
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$449 Roundtrip, found 5 hours ago
$449
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Apr 24 from Midway Intl. to Southwest Florida Intl., returning Sun, Apr 26, priced at $449 found 5 hours ago

Airfares from $45 One Way, $90 Round Trip from Chicago to Naples

Prices starting at $90 for return flights and $45 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.

Sun, Apr 26 - Thu, Apr 30
ORD
Chicago
RSW
Fort Myers
$90 Roundtrip, found 19 hours ago
$90
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sun, Apr 26 from Chicago to Fort Myers, returning Thu, Apr 30, priced at $90 found 19 hours ago
Sun, Apr 26 - Thu, Apr 30
ORD
Chicago
RSW
Fort Myers
$90 Roundtrip, found 19 hours ago
$90
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from Chicago to Fort Myers, returning Thu, Apr 30, priced at $90 found 19 hours ago
Sun, Apr 26 - Thu, Apr 30
ORD
Chicago
RSW
Fort Myers
$167 Roundtrip, found 19 hours ago
$167
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sun, Apr 26 from Chicago to Fort Myers, returning Thu, Apr 30, priced at $167 found 19 hours ago
Thu, May 28 - Mon, Jun 1
ORD
Chicago
RSW
Fort Myers
$235 Roundtrip, just found
$235
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, May 28 from Chicago to Fort Myers, returning Mon, Jun 1, priced at $235 just found
Sat, May 2 - Sat, May 9
ORD
Chicago
RSW
Fort Myers
$292 Roundtrip, found 4 hours ago
$292
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, May 2 from Chicago to Fort Myers, returning Sat, May 9, priced at $292 found 4 hours ago

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
4.0-star property

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

9.2/10 Wonderful! (2,293 reviews)

Jun 10 - Jun 15

5 night stay

Chicago (MDW) to Fort Myers (RSW)

Southwest Airlines • Roundtrip • Coach
Price was $1,102, price is now $812 per person
$812
per person
found 23 hours ago
Beautiful large pools both rooftop and ground level. Brand new fitness center. Clean and nice.

Reviewed on Mar 21, 2026

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

LaPlaya Beach & Golf Resort - A Noble House Resort

9/10 Wonderful! (1,002 reviews)

May 24 - May 31

7 night stay

Chicago (CHI) to Fort Myers (RSW)

Southwest Airlines • Coach

Fort Myers (RSW) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $3,026, price is now $1,950 per person
$1,950
per person
found 1 day ago
Great customer service and guest services. Nice resort and good food.....we will definitely be back again.....

Reviewed on Jul 1, 2025

The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

9.4/10 Exceptional! (748 reviews)

May 24 - May 31

7 night stay

Chicago (CHI) to Fort Myers (RSW)

Southwest Airlines • Coach

Fort Myers (RSW) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $1,471, price is now $985 per person
$985
per person
found 1 day ago
Nice and clean with a great view and pool area

Reviewed on Nov 13, 2025

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Naples packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Fort Myers Colonial Blvd
3.0-star property

Home2 Suites by Hilton Fort Myers Colonial Blvd

9.4/10 Exceptional! (669 reviews)

May 20 - May 25

5 night stay

Chicago (CHI) to Fort Myers (RSW)

United • Roundtrip • PremiumEconomy
Price was $1,166, price is now $985 per person
$985
per person
found 24 hours ago
Very clean. Great staff. Beautiful rooms.

Reviewed on Sep 21, 2024

Embassy Suites by Hilton Fort Myers Estero
3.5-star property

Embassy Suites by Hilton Fort Myers Estero

9.2/10 Wonderful! (1,155 reviews)

May 20 - May 25

5 night stay

Chicago (CHI) to Fort Myers (RSW)

United • Roundtrip • PremiumEconomy
Price was $1,192, price is now $1,016 per person
$1,016
per person
found 24 hours ago
Excellent place to stay. And breakfast was great

Reviewed on Aug 6, 2025

Hampton Inn & Suites Fort Myers-Estero/FGCU
2.5-star property

Hampton Inn & Suites Fort Myers-Estero/FGCU

9.2/10 Wonderful! (1,008 reviews)

May 20 - May 25

5 night stay

Chicago (CHI) to Fort Myers (RSW)

United • Roundtrip • PremiumEconomy
Price was $1,214, price is now $1,060 per person
$1,060
per person
found 24 hours ago
Staff person was really nice and greeted us at the front desk. As for the room It was really nice and roomie, but I would like to see a table on the other side of each bed with phone charging stations and lights to read by. overall, the room was very nice.

Reviewed on Oct 31, 2025

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Naples first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Boat House
2.0-star property

The Boat House

9.2/10 Wonderful! (684 reviews)

May 28 - May 31

3 night stay

Chicago (CHI) to Fort Myers (RSW)

American Airlines • Roundtrip • FirstClass
Price was $1,271, price is now $1,104 per person
$1,104
per person
found 5 hours ago
Good spot old town Marco

Reviewed on Aug 2, 2025

JW Marriott Marco Island Beach Resort
4.0-star property

JW Marriott Marco Island Beach Resort

9/10 Wonderful! (1,002 reviews)

May 28 - May 31

3 night stay

Chicago (CHI) to Fort Myers (RSW)

American Airlines • Roundtrip • FirstClass
Price was $2,311, price is now $1,958 per person
$1,958
per person
found 5 hours ago
The rooms was clean the staff very friendly,the hotel have a large choose of amenities.

Reviewed on Nov 18, 2025

Bellasera Resort
4.0-star property

Bellasera Resort

9.6/10 Exceptional! (2,266 reviews)

May 28 - May 31

3 night stay

Chicago (CHI) to Fort Myers (RSW)

American Airlines • Roundtrip • FirstClass
Price was $1,646, price is now $1,422 per person
$1,422
per person
found 5 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

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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

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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.

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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.