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

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Lowest round trip fares by airline from Chicago and Naples

Cheapest prices ($34 One Way, $87 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
Naples
The price is $165 per night from Nov 28 to Nov 29
$165
includes taxes & fees
$149 per night
Nov 28 - Nov 29
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,007 reviews)
"Great location for the affordability. Close to 5th Ave where all the dining and shopping is located in downtown Naples. Convenient to the bleach, only a few blocks away. Will stay here again."

Reviewed on Nov 17, 2024

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 $138 per night from Dec 10 to Dec 11
$138
includes taxes & fees
$124 per night
Dec 10 - Dec 11
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,001 reviews)
"Great property"

Reviewed on Nov 20, 2024

Fairways Inn of Naples
Naples Garden Inn

Naples Garden Inn

2.5 out of 5
2630 Tamiami Trail North, Naples, FL
The price is $179 per night from Dec 22 to Dec 23
$179
includes taxes & fees
$161 per night
Dec 22 - Dec 23
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
7.8/10 Good! (1,000 reviews)
"Nice, comfortable room in a good location."

Reviewed on Nov 11, 2024

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
Earliest Flight Departure Date
Latest Flight Departure Date
Popular 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.