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Cheap Flights from Chicago to Naples & Flight Information
Origin airport IATA code
CHI
Destination airport IATA code
APF
Number of flight options
2
Average flight time
3 hours 53 mins

Naples RSW Flight Information

Traveling From
Chicago
Origin Airport IATA Code
CHI
Traveling To
Naples
Destination Airport IATA Code
APF
Number of Airlines Serving
8
Available Airlines
Distance
1807 km
Direct Flight Time
2 50
Flight Price

Fly from Chicago to Naples with ebookers

Cheap flights from Chicago to Naples 

Our advanced search tools and comprehensive filters help you find a flight that fits your budget. To search for cheap flights, just enter your travel dates and sort your results by price. With all available tickets listed lowest price first, it’s easy to select the one that’s easiest on your wallet.  

To find the cheapest flights from Chicago to Naples, you can also travel outside peak season. The more flexible you can be on travel dates, the easier it is to find those cheap flight tickets. We know, for example, that the cheapest time to travel between Chicago to Naples is . In the current list of deals available, prices start at and can rise to for return flights.  

Find the best flight from Chicago to Naples  

Every day between Chicago and Naples, 22 flights from 8 airlines jet back and forth. And with ebookers, you can book tickets for any one of those flights. If you book a direct flight with American Airlines, Alaska Airlines, Air Canada, Emirates, Southwest Airlines, Swiss, United Airlines, Spirit Airlines, you’ll arrive safely in your destination in around 2hours. If you can think of a quicker way to cover the 1807 km between null and null, let us know! 

Flights from Chicago to Naples — a great choice on great deals 

We only need a little information to give you a lot of choice. Just tell us when you’re planning your family holiday, long weekend, luxury getaway or quick business trip, and we’ll do the rest. And to keep your choice-making easy, we’ve given you plenty of ways to narrow down your search. Choose one-way, roundtrip or multi city flights, select your preferred airline, your time of arrival and departure and cabin class using the filters.  

Once you’ve told us what you want, we’ll show you what’s on offer. All you need to do is take your pick and start packing.  

Book your flights with ebookers 

We want the experience of booking your flight from Chicago to Naples to be as simple as possible. That’s why we designed our search and filter options to make your life easy. Whether you are travelling on business or for pleasure, ebookers has you covered. 

When you’re ready to book, our service is always fast and transparent. We know plans change, so we have a range of flexible booking options. Choose between refundable bookings and flights with no charges should you need to rearrange and travel stress-free. 

Need a car after flight from Chicago to Naples

Place to stay after flight from Chicago to Naples

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Stay at this luxury hotel in Naples. Enjoy 3 outdoor pools, 3 restaurants and a full-service spa. Our guests praise the breakfast and the pool in their reviews. ...
8.4/10 Very Good! (1,189 reviews)
"Lived the solitude of The Villas and proximity to the lap pool"

Reviewed on 25 Mar 2024

Naples Grande Beach Resort
Comfort Inn Naples East I-75

Comfort Inn Naples East I-75

2.5 out of 5
3860 Tollgate Blvd, Naples, FL
Stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi and free parking. Popular attractions Paradise Coast Sports Compex and Swamp ...
8/10 Very Good! (722 reviews)
A simple but pleasant stay
"Clean. Comfortable. Close to interstate. Staff friendly. Loved the mirror arrangement in bathroom selection. It allows u to see the back of ur hair for blowdrying and styling. A rare find for that. Pool looked nice but it use it. Did see pool guy cleaning in the morning. So u know they clean it daily. ..."

Reviewed on 24 Mar 2024

Comfort Inn Naples East I-75
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,059 reviews)
"Overall was good, front desk personel was very friendly. The shampoo and conditioner bottle were empty. I stayed 3 nights and on one of the days no one came to clean the room or bring towels. The next day they cleaned the room and brought towels but the shampoo bottles were empty again."

Reviewed on 27 Mar 2024

La Quinta Inn & Suites by Wyndham Naples Downtown
Save an average of 15% on thousands of hotels when you're signed in
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S, Naples, FL
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace and a free beach shuttle. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,002 reviews)
Great Hotel
"Great hotel walking distance to everything."

Reviewed on 24 Mar 2024

Inn on Fifth
Best Western Naples Plaza Hotel

Best Western Naples Plaza Hotel

2.5 out of 5
6400 Dudley Dr, Naples, FL
Stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff in their ...
8.6/10 Excellent! (1,002 reviews)
"Well breakfast was the best part. Great fresh food cooked perfect. Unfortunately only w clothes dryers available and they were busy all day. Also some gym equipment was broken."

Reviewed on 27 Mar 2024

Best Western Naples Plaza Hotel
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
1221 5th Ave S, Naples, FL
Stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking and a marina. Our guests praise the restaurant and the bar in their reviews. Popular ...
8.4/10 Very Good! (1,195 reviews)
"Excellent experience, great service and staff"

Reviewed on 28 Mar 2024

Bayfront Inn Fifth Avenue
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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.

*Savings based on all holiday package bookings with Flight + Hotel on ebookers.com from January 2017 to December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

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. 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.