- Must visit
The Baker Museum
Regional art museum at Artis—Naples with rotating exhibitions, modern and classic works, and strong programming in a polished setting.
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Journey information
Overview: Chicago, IL to Naples, FL flight
USAUSA
Flights from Chicago, IL to Naples, FL depart on average 44 times per day, taking around 5h 21m. Cheap flight tickets for this journey start at $91 if you book in advance.
There are 6 flights per day. The earliest flight runs at 05:00, the last at 22:05. The fastest flight covers the 1135 miles (1827 km) distance in 2h 47m. January is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 1135 miles (1827 km) |
Average flight duration 5h 21m |
Cheapest ticket price $91 |
Flights per day 44 |
Direct flights 6 |
Fastest flight 2h 47m |
First flight 5:00 AM |
Last flight 10:05 PM |
Cheapest Month Jan |
Cheapest Day Mon |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 3 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Frequently asked questions about your Chicago, IL to Naples, FL trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Naples, FL.
Cheap plane tickets from Chicago, IL to Naples, FL can start from as little as $91 when you book in advance. The average flight ticket price for Chicago, IL to Naples, FL is $661 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The earliest flight from Chicago, IL to Naples, FL leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Naples, FL leaves at 10:05 PM.
Yes, there are 6 direct flights a day from Chicago, IL to Naples, FL with American Airlines, United, Spirit Airlines, Allegiant Air. Schedules can vary on holidays or weekends with fewer direct flights.
Live departures
Chicago, IL to Naples, FL flight times
The table below shows live departures for Chicago, IL to Naples, FL flights for today, Monday, November 2. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 | 11:30 AM Chicago, IL | 2h47 | 2:17 PM Naples, FL | 0 transfersDirect | |
| 12:20 PM Chicago, IL | 2h56 | 3:16 PM Naples, FL | 0 transfersDirect | |
| 1:20 PM Chicago, IL | 2h56 | 4:16 PM Naples, FL | 0 transfersDirect | |
| 11:22 PM Chicago, IL | 2h58 | 2:20 AM Naples, FL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Why should you book Chicago, IL to Naples, FL flights with Omio?
American Airlines as well as United, JetBlue Airways, Spirit Airlines, Allegiant Air and more offer flights services from Chicago, IL to Naples, FL.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Naples, FL.
Why book with Omio vs American Airlines?
- Compare with other providers: On Omio, you can not only buy tickets for American Airlines, but also compare tickets for the likes of United, JetBlue Airways, Spirit Airlines or Allegiant Air to find the best option for your trip from Chicago, IL to Naples, FL.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare American Airlines with all available travel options, which are bus and flight to ensure you get the best deal for traveling from Chicago, IL to Naples, FL.
Why book with Omio over Trip, Edreams or Skyscanner?
- Compare with other providers: On Omio, you can also compare tickets for the likes of United, JetBlue Airways, Spirit Airlines or Allegiant Air to find the best option for your trip from Chicago, IL to Naples, FL.
- Multiple modes of transport: Omio allows you to compare travel options including bus and flight to find the ideal travel option from Chicago, IL to Naples, FL.
Airlines: United, American Airlines, JetBlue Airways, Spirit Airlines, Allegiant Air, Sun Country Airlines from Chicago, IL to Naples, FLFind the best flights between Chicago, IL to Naples, FL with Omio's travel partners United, American Airlines, JetBlue Airways, Spirit Airlines, Allegiant Air, Sun Country Airlines from $91. We can find you the best deals, schedules and tickets when comparing and booking the best trip.
United
About
United Airlines, established in 1926, is a major U.S. airline headquartered in Chicago, Illinois. Operating an extensive domestic and international network, United serves more destinations than any other airline, connecting travelers across six continents. The airline's eight hubs include Chicago–O'Hare, Denver, Houston–Intercontinental, Los Angeles, Newark, San Francisco, Washington–Dulles, and Guam. As a founding member of the Star Alliance, United offers a comprehensive range of services, including regional flights through United Express, catering to both leisure and business travelers. The airline is committed to sustainability, investing in sustainable aviation fuel and innovative technologies to reduce its environmental impact.
Luggage & cancellation policy
Average United Duration
2h 58m
Cheapest United Price
$195
United frequency
30 a day
Luggage included
Carry-on baggage allowance is 7kg total (2 pieces max. ) for both Choice and Flex fares on United Airlines and Virgin Australia flights.
Additional luggage
Excess baggage fees apply for additional checked luggage beyond the standard allowance.
Luggage storage
Both airlines provide checked baggage services for storing luggage during flights.
Cancellation Policy
Cancellation fees apply per person, per booking, with specific fees for different fare types.
Refund
Not applicable to flights; however, full refunds are available if flights are canceled by the airline.
Pregnant on board
Pregnant passengers are permitted to travel, with specific guidelines and medical certificates required after a certain gestational period.
Unaccompagned minor
Unaccompanied minors are permitted to travel, with specific age restrictions and services provided.
Amenities on board the airplane
Wifi
Food sold onboard
Meals and snacks are included on international flights operated by United Airlines and Virgin Australia.
Seat reservation
Seat selection may incur additional fees, depending on the fare type and airline.
Toilets
USB plugs
Accessibility
United Airlines and Virgin Australia offer services to and within Australia, providing accessible travel options for passengers with mobility needs.
Bikes
Both airlines permit bicycles onboard, with specific guidelines and fees.
Pets
United Airlines and Virgin Australia allow pets onboard, subject to specific policies and fees.
JetBlue Airways
About
JetBlue Airways is a U.S.-based low-cost airline headquartered in Long Island City, New York. Established in 1998, it operates over 850 daily flights to 86 destinations across the U.S., Caribbean, and Latin America. The airline is known for its customer-friendly services, including complimentary Wi-Fi, free snacks, and spacious seating. JetBlue's fleet comprises various Airbus models, such as the A220, A320, and A321, as well as the Embraer E190. The company is committed to sustainability and has implemented initiatives to reduce its environmental impact. Joanna Geraghty serves as the CEO, leading a team of approximately 23,000 employees.
Luggage & cancellation policy
Average JetBlue Airways Duration
5h 24m
Cheapest JetBlue Airways Price
$254
JetBlue Airways frequency
5 a day
Luggage included
JetBlue's standard fare includes one checked bag and one carry-on bag.
Additional luggage
Additional luggage can be added for a fee, subject to availability.
Luggage storage
JetBlue offers overhead bin space for carry-on luggage and checked baggage services.
Cancellation Policy
JetBlue allows cancellations within 24 hours of booking for a full refund; after 24 hours, cancellation fees may apply.
Pregnant on board
JetBlue allows pregnant passengers to fly up to 36 weeks gestation without a medical certificate.
Unaccompagned minor
JetBlue allows unaccompanied minors aged 5-13 to travel for a fee, with specific guidelines.
Amenities on board the airplane
Wifi
Food sold onboard
JetBlue offers complimentary snacks and non-alcoholic beverages on all flights.
Seat reservation
JetBlue offers Even More Space seats for an additional fee, providing extra legroom and priority boarding.
Toilets
USB plugs
Accessibility
JetBlue Airways provides accessible services for passengers with disabilities, including wheelchair assistance and priority boarding.
Bikes
JetBlue accepts bicycles as checked baggage for a fee, with specific packaging requirements.
Pets
JetBlue allows pets in the cabin for a fee, with specific guidelines on pet carriers and weight limits.
American Airlines
About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average American Airlines Duration
2h 49m
Cheapest American Airlines Price
$245
American Airlines frequency
19 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Sun Country Airlines
Luggage & cancellation policy
Average Sun Country Airlines Duration
5h 2m
Cheapest Sun Country Airlines Price
$303
Sun Country Airlines frequency
2 a day
Luggage included
One personal item (17 x 13 x 9 inches) included
Additional luggage
Checked bags available for purchase, fees vary by route
Cancellation Policy
Refunds available within 24 hours of booking, after that fees apply based on fare type
Pregnant on board
Pregnant passengers can travel up to 36 weeks (32 weeks for multiple pregnancies). Medical certificate required after 28 weeks
Unaccompagned minor
Unaccompanied minor service available for children 5-14 years old, fee applies, must be booked in advance
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Wheelchair assistance available with 48-hour advance notice
Spirit Airlines
About
Spirit Airlines is an American ultra-low-cost carrier, headquartered in Dania Beach, Florida, operating scheduled flights throughout the United States, the Caribbean, and Latin America. Known for its distinctive bright yellow planes, Spirit's business model traditionally focuses on offering low base fares by unbundling services, allowing passengers to pay only for the amenities they choose, such as baggage and seat selection. As of August 2024, Spirit is evolving its offerings, introducing new fare tiers like "Go Big," "Go Comfy," "Go Savvy," and "Go," which include various bundled perks such as wider seats, extra legroom, priority boarding, and in-flight refreshments. Spirit was the seventh largest passenger carrier in North America as of 2023.
Luggage & cancellation policy
Average Spirit Airlines Duration
2h 47m
Cheapest Spirit Airlines Price
$127
Spirit Airlines frequency
1 a day
Luggage included
Personal item (18 x 14 x 8 inches) included
Additional luggage
Checked bags: First bag $79-89, Second bag $89-99, Additional bags $105-110
Cancellation Policy
Cancellation within 24 hours of booking is free, after that fees apply based on fare type and timing
Pregnant on board
Up to 7 days before departure with medical certificate. After 28 weeks, medical certificate required
Unaccompagned minor
Ages 5-14 can travel as unaccompanied minors for $100 fee per direction. Service not available on international flights or connecting flights
Amenities on board the airplane
Wifi
Accessibility
Spirit Airlines offers assistance for passengers with disabilities, including wheelchair services and priority boarding. Passengers are encouraged to request assistance at least 48 hours in advance to ensure availability.
Allegiant Air
About
Allegiant Air is an American ultra-low-cost airline headquartered in Las Vegas, Nevada, founded in 1997. It focuses on providing affordable, nonstop leisure travel from small and medium-sized cities to popular vacation destinations, primarily in warm-weather locations like Florida and the Southwest. Allegiant operates on an ultra-low-cost business model, offering low base fares and generating significant revenue through add-on fees for services like baggage and seat assignments. The airline serves over 120 domestic destinations and emphasizes direct sales through its website.
Luggage & cancellation policy
Average Allegiant Air Duration
2h 48m
Cheapest Allegiant Air Price
$91
Allegiant Air frequency
1 a day
Luggage included
Personal item (free): 16x15x7 under seat. No cabin bag included.
Additional luggage
Carry-on bag: $50-$75. Checked bag: $50-$75 per bag.
Cancellation Policy
Non-refundable tickets. Changes permitted for fee plus fare difference.
Pregnant on board
Must present medical certificate if traveling after 7th month of pregnancy. Not permitted to fly within 7 days of due date.
Unaccompagned minor
Ages 15-17 can travel alone. Ages 5-14 must use unaccompanied minor service ($50 fee each way).
Amenities on board the airplane
Accessibility
Allegiant Air offers assistance for passengers with disabilities, including wheelchair services and priority boarding. Passengers are encouraged to request assistance at least 48 hours in advance to ensure proper arrangements.
Pets
Small pets in cabin: $50 each way. Must be in carrier under seat.
Companies, tickets, and onboard amenities between Chicago, IL and Naples, FL
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
When taking a flight from Chicago, IL to Naples, FL, you can count on American Airlines, United, JetBlue Airways, Spirit Airlines, Allegiant Air, Sun Country Airlines for the best way to get you to Naples, FL. You can also check all possible airlines who offer a service between Chicago, IL and Naples, FL and compare the amenities they offer before buying a plane ticket.
For international flights we recommend to arrive 2.5 to 3 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
Complete guide to Naples, FL
Things to do in Naples, FL
Discover the best of Naples, FL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Naples, FL trip today.
- Recommended
Naples Depot Museum
Local history museum in a restored rail depot with exhibits on Naples development, transport, and Southwest Florida heritage.
- Recommended
Golisano Children's Museum of Naples
Children’s museum with hands-on science, creativity, and nature exhibits designed for families seeking interactive indoor activities.
- Must visit
Fifth Avenue South
Upscale downtown street for strolling, shopping, galleries, and seasonal events, framed by palms and elegant architecture.
- Must visit
Naples Botanical Garden
Botanical garden with tropical landscapes, themed sections, and accessible paths offering a calm break from the beach.
- Recommended
Third Street South
Historic district and waterfront shopping area with gardens, galleries, and shaded streets ideal for a relaxed walk.
- Gluten-free
Stone Crab Claws
Stone crab claws are a Southwest Florida classic, served chilled with mustard sauce. The local fishery and short season make them a signature Naples seafood treat.
Grouper Sandwich
Grouper sandwich is a Gulf Coast staple: fresh local grouper, usually grilled or fried, on a bun. It is a go-to casual seafood order across Naples.
Conch Fritters
Conch fritters are a Florida coastal favorite made with chopped conch in seasoned batter, then fried. They reflect the region’s tropical and maritime food culture.
Truluck's Ocean's Finest Seafood and Crab
Upscale seafood restaurant focused on Florida fish, shellfish, and polished service in an elegant Old Naples setting.
USS Nemo Restaurant
Popular casual spot serving fresh Gulf seafood, raw bar items, and Southern coastal dishes in a relaxed local setting.
The Dock At Crayton Cove
Historic casual seafood house known for stone crab, fish, and a lively Old Naples atmosphere near the water.
United States Dollar ($)
Naples is pricier than many Florida towns, with higher hotel and dining costs in season, but casual meals and driving-based transport keep overall visitor costs moderate.
Average meal costs
- Budget
- $12-18 for fast food or a casual lunch.
- Mid-range
- $25-45 per person for a restaurant meal.
- Fine dining
- $60+ per person at upscale restaurants.
- Coffee
- $4-6 for coffee at a cafe.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, and round up or add 10-15% for taxis. Cafe tipping is optional but appreciated.
Plan your visit to Naples, FL
Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Naples, FL.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Naples, FL, travelers should be cautious of petty theft and pickpocketing, especially in crowded areas and popular beach spots. Common scams include overcharging by taxis or ride services and timeshare sales pressure tactics. It’s advisable to use authorized transportation and stay alert in busy tourist areas to avoid these issues.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
FAQs: Chicago, IL to Naples, FL Flight
Find answers to the most common questions about traveling from Chicago, IL to Naples, FL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Naples, FL, this guide helps you travel smarter and with confidence.
It's helpful to compare your options as there are 2 ways to travel between Chicago, IL and Naples, FL including taking a bus and flight.
popular airports
Popular airports from Chicago, IL to Naples, FL
Most Chicago, IL to Naples, FL flights use the O'Hare International Airport to airport pair. Use this guide to compare Chicago, IL and Naples, FL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Chicago
Arrival airports in Naples
Which Chicago, IL airport do flights to Naples, FL leave from?
Flights from Chicago, IL to Naples, FL depart from O'Hare International Airport. The airport is 2 miles (4 km) from Chicago, IL city centre at 10000 W O'Hare Ave, Chicago, IL 60666, USA.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · $6 · every ~23 min
O'Hare International Airport airport facilities and services
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Midway International Airport (MDW)5700 S Cicero Ave, Chicago, IL 60638, USA
City-centre transport
Getting to Midway International Airport from Chicago city centre
Midway International Airport is 4 km from Chicago city centre. Public transport options include:
Bus62 · 40m · $4
62 · 52m · $5 · every ~12 min
SubwayOrange Line · 20m · $6 · every ~15 min
Orange Line · 34m · $6 · every ~15 min
Midway International Airport airport facilities and services
Midway International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are available, including locations like Concourse A and B with options like Harry Caray's and Potbelly Sandwich Shop.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout the airport, including near gates and baggage claim.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at Midway International Airport: Parking, Taxis, WC.
Bike and car services
Available at Midway International Airport: Car Rental.
Accessibility
Accessibility facilities are available at Midway International Airport: Ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels are available within walking distance, such as the Hyatt Place Chicago Midway Airport..
Most popular flights from Chicago, IL
More options for your journey from Chicago, IL to Naples, FL
Here are some other resources that might have the information you need
Most popular flights to and from Naples, FL and Chicago, IL
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