$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 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$248 Roundtrip, found 4 hours ago
$248
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $248 found 4 hours ago
Fri, Apr 24 - Tue, Apr 28
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$423 Roundtrip, found 4 hours ago
$423
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Apr 24 from Midway Intl. to Southwest Florida Intl., returning Tue, Apr 28, priced at $423 found 4 hours ago
Fri, Apr 24 - Sun, Apr 26
RFD
Greater Rockford
RSW
Southwest Florida Intl.
$438 Roundtrip, found 1 day ago
$438
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Apr 24 from Greater Rockford to Southwest Florida Intl., returning Sun, Apr 26, priced at $438 found 1 day ago

Airfares from $45 One Way, $113 Round Trip from Chicago to Naples

Prices starting at $113 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 - Sat, May 2
ORD
Chicago
RSW
Fort Myers
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Apr 26 from Chicago to Fort Myers, returning Sat, May 2, priced at $113 found 1 day ago
Thu, Apr 30 - Sat, May 9
ORD
Chicago
RSW
Fort Myers
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Fort Myers, returning Sat, May 9, priced at $121 found 1 day ago
Wed, May 27 - Wed, Jun 3
MDW
Chicago
RSW
Fort Myers
$199 Roundtrip, found 14 hours ago
$199
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Wed, May 27 from Chicago to Fort Myers, returning Wed, Jun 3, priced at $199 found 14 hours ago
Fri, Sep 18 - Sat, Sep 19
ORD
Chicago
RSW
Fort Myers
$275 Roundtrip, found 2 hours ago
$275
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Sep 18 from Chicago to Fort Myers, returning Sat, Sep 19, priced at $275 found 2 hours ago
Fri, Sep 18 - Sat, Sep 19
ORD
Chicago
RSW
Fort Myers
$286 Roundtrip, found 2 hours ago
$286
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Sep 18 from Chicago to Fort Myers, returning Sat, Sep 19, priced at $286 found 2 hours ago

Naples economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0-star property

The Suites at Fishermen’s Village- 2 Bedroom Suites

9.8/10 Exceptional! (1,146 reviews)

Jun 12 - Jun 16

4 night stay

Chicago (CHI) to Fort Myers (RSW)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $829, price is now $563 per person
$563
per person
found 1 day ago
My college friends and I loved this hotel! We are now adults and appreciated the absolute cleanliness and friendliness of the staff. I will be referring this hotel to all my friends for future visits to this area!

Reviewed on Mar 30, 2025

Matanzas Inn Bayside Resort and Marina
3.0-star property

Matanzas Inn Bayside Resort and Marina

9.4/10 Exceptional! (1,008 reviews)

May 25 - May 29

4 night stay

Chicago (CHI) to Fort Myers (RSW)

Southwest Airlines • Coach

Fort Myers (RSW) to Chicago (CHI)

American Airlines • Coach
Price was $924, price is now $612 per person
$612
per person
found 1 day ago
This is the best location and our view of the Bay was amazing. Loved having the kitchen and balcony. The A/C worked great.

Reviewed on Mar 9, 2026

Marriott Sanibel Harbour Resort & Spa
4.0-star property

Marriott Sanibel Harbour Resort & Spa

8.4/10 Very Good! (1,009 reviews)

May 23 - May 27

4 night stay

Chicago (ORD) to Fort Myers (RSW)

Southwest Airlines • Coach

Fort Myers (RSW) to Chicago (ORD)

American Airlines • Coach
Save 100% on your flight
Price was $1,118, price is now $772 per person
$772
per person
found 1 day ago
Wonderful stay, but with some glitches. This resort hotel is conveniently located next to the (toll) bridge that goes into Sanibel Island. We requested a hypoallergenic room, and the hotel delivered! We had a beautiful view from our balcony deck. Our email notified us that the hotel was ready to check us in the previous evening. So, when we arrived, we were prepared to go to our room. However, the hotel said our room wasn’t ready. We were left a couple of hours without a room. When we tried calling to get updates, their phone wouldn’t answer. This went on for at least 20 minutes of calling the hotel. We reported the issue to the front desk. The common areas have a very strong deodorizer smell from Ecolabs. It’s very off putting especially for a nice resort. It’s a smell associated with cheap motels and public restrooms, honestly. The smell should be toned down, especially since it makes its way to the dining areas. Overall, we had a nice time.

Reviewed on Apr 12, 2026

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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 1 day 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 1 day 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 1 day 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 1 day 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 1 day 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 1 day 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

Orbitz is the best place to find guaranteed low prices on Chicago to Naples flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.

Find Cheap Chicago to Naples Flights

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Discount Travel Planning Made Simple

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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.