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Lowest round trip fares by airline from Chicago and Naples

Cheapest prices ($21 One Way, $65 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 $129 per night from Jun 1 to Jun 2
$129
per night
Jun 1 - Jun 2
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 ...
8.8/10 Excellent! (1,003 reviews)
"The hotel room is very clean. The people working are also very friendly. However, you can hear a lot of traffic noise in the room because the window is single pane. Overall is excellent"

Reviewed on Apr 29, 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 $125 per night from May 31 to Jun 1
$125
per night
May 31 - Jun 1
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! (1,003 reviews)
"Great place. Very nice staff."

Reviewed on May 7, 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 $98 per night from May 21 to May 22
$98
per night
May 21 - May 22
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ...
7.8/10 Good! (999 reviews)
"Laid back and good location"

Reviewed on May 6, 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
14
Earliest Flight Departure Date
May 17
Latest Flight Departure Date
May 17
Popular Airlines
United Airlines

Cheap flights from Chicago to Naples

Are you ready to book your flight, but feeling nervous about paying too much if the price drops? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus a $50 CheapCash bonus, which you can use to save on your hotel reservation.

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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

Going cheap doesn't mean giving up great service. Our agents are available 24/7 to help you find the right cheap flights and hotel, and to answer questions about your trip.

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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.