Cheap flights from Chicago (CHI) to Naples (APF)

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Lowest round trip fares by airline from Chicago and Naples

Cheapest prices ($38 One Way, $46 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Naples

Naples Park Central Hotel

Naples Park Central Hotel

2.5 out of 5
40 9th Street North, Naples, FL
The price is $87 per night from Dec 12 to Dec 12
Located in Old Naples, this hotel is within a 10-minute walk of Naples Regional Library and Fifth Avenue South. Naples Beach and Tin City are also within 1 mi ...
4/5 Very Good! (5 reviews)
"Angie was very pleasant and everyone was very nice, I will go back again"

Reviewed on Oct 5, 2021

Naples Park Central Hotel
Fairways Inn of Naples

Fairways Inn of Naples

2.5 out of 5
103 Palm River Blvd, Naples, FL
The price is $85 per night from Dec 15 to Dec 15
Located in Palm River Estates, this hotel is 2.3 mi (3.7 km) from North Collier Regional Park and 2.8 mi (4.5 km) from Mercato. Delnor-Wiggins Pass State Park ...
4.8/5 Exceptional! (4 reviews)
"We thought the landscaping and central courtyard was beautiful. Areas to sit and relax, outside barbeques provided and water features were just some of the things we appreciated and enjoyed as well as the beautiful breakfast area. Some rooms opened to the beautifully landscaped courtyard. The room ..."

Reviewed on Aug 14, 2021

Fairways Inn of Naples
Naples Garden Inn

Naples Garden Inn

2.5 out of 5
2630 Tamiami Trail North, Naples, FL
The price is $102 per night from Dec 6 to Dec 6
Located in Sun Terrace, this hotel is within 2 mi (3 km) of Coastland Center, Naples Zoo at Caribbean Gardens, and Lowdermilk Beach Park. Naples Beach and Fifth ...
3.7/5 Good! (6 reviews)
Close to thebeach
"The lady in thw front desk was so nice and helpful. Its close to the beach. I like it a lot"

Reviewed on Apr 4, 2018

Naples Garden Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Naples

Origin Chicago
Destination Naples
Number of Daily Flights 18
Earliest Flight Departure Date Dec 11
Latest Flight Departure Date Dec 12
Popular Airlines Spirit Airlines

Cheap flights from Chicago to Naples

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Save Even More Time and Money With a Naples Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Naples vacation that you can't get when you book flights and hotel separately.

Relax in Naples With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.