- Must visit
The Baker Museum
Naples flagship art museum at Artis—Naples, known for modern and contemporary art exhibitions and a strong regional profile.
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Journey information
Overview: Chicago, IL to Naples, FL flight
USAUSA
Flights from Chicago, IL to Naples, FL depart on average 51 times per day, taking around 2h 49m. Cheap flight tickets for this journey start at $82 (€67) if you book in advance.
There are 9 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 2h 49m |
Cheapest ticket price $82 (€67) |
Flights per day 51 |
Direct flights 9 |
Fastest flight 2h 47m |
First flight 5:00 AM |
Last flight 10:05 PM |
Cheapest Month Jan |
Cheapest Day Thu |
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
The cheapest and fastest flights from Chicago, IL to Naples, FL
Showing times and prices for Jun 21
Cheapest price
$148
Average price
$149
Fastest journey
2 h 48 m
Average duration
2 h 48 m
Flights per day
2
Distance
1827 km
Cheap tickets
The best way to find a cheap flight ticket from Chicago, IL to Naples, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Naples, FL will cost around $149 if you buy it on the day, but the cheapest tickets can be found for only $148.
Fast flights
Of the 2 flights that leave Chicago, IL for Naples, FL onSun, Jun 21, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Jun 21 the direct flights cover the 1827 km distance in an average of 2 h 48 m but if you time it right, some flights will get you there in just 2 h 48 m .
On Sun, Jun 21 the longest flights will take 2 h 48 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
12:36 AM2h48Chicago, IL3:24 AMNaples, FL$1481One-way0 transfers- 12:42 AM2h48Chicago, IL3:30 AMNaples, FL$1501One-way0 transfers
- 12:36 AM2h48Chicago, IL3:24 AMNaples, FL$1481One-way0 transfers
- 12:42 AM2h48Chicago, IL3:30 AMNaples, FL$1501One-way0 transfers
Travel Information
Compare bus and flight for Chicago, IL to Naples, FL
Omio recommends booking the flight as it is the most popular option from Chicago, IL to Naples, FL among Omio's users. If you are prioritising price take the flight with prices starting from $82. For those with little time consider booking a flight which can get you there in 2h 49m. The ticket price range depends on the travel mode: a flight costs an average of $82, and a bus costs an average of $150.
Distance: 1135 miles (1827 km)
Compare flight with
Most popular Flight | Bus | Driving |
|---|---|---|
$172 Average price Cheapest | $275 Average price | $254 Average price (fuel + tolls) |
5h 49m Average total duration Fastest 2h 49m Onboard + 3h 0m Additional time* | 41h 45m Average total duration 41h 15m Onboard + 30m Additional time* | 19h 44m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Chicago, IL to Naples, FL is a flight with an average price of $172 (€141).
This is compared to other travel options from Chicago, IL to Naples, FL:
A flight is $102 (€84) less than a bus for this route with tickets for a bus from Chicago, IL to Naples, FL costing on average $275 (€225).
The fastest way to travel from Chicago, IL to Naples, FL is by flight with an average journey time of 2h 49m.
Other travel options to Naples, FL take longer:
Bus takes on average 41h 15m.
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.
We recommend using the flight as it is the most popular way to get from Chicago, IL to Naples, FL among Omio's users.
Live departures
Chicago, IL to Naples, FL flight times
The table below shows live departures for Chicago, IL to Naples, FL flights for tomorrow, Saturday, June 20. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 12:36 AM Chicago, IL | 2h48 | 3:24 AM Naples, FL | 0 transfersDirect | |
| 12:42 AM Chicago, IL | 2h48 | 3:30 AM Naples, FL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Naples, FL by bus or flight
Compare bus and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Why should you book Chicago, IL to Naples, FL flights with Omio?
American Airlines operates all 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?
- 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?
- 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: American Airlines from Chicago, IL to Naples, FLFind the best flights between Chicago, IL to Naples, FL with Omio's travel partners American Airlines from $82 (€67). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
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 Duration
2h 49m
Cheapest Price
$96 (€79)
American Airlines frequency
23 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.
Entertaiment on board
Complete guide to Naples
Things to do in Naples
Discover the best of Naples — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Naples trip today.
- Recommended
The Revs Institute
Specialized museum of automotive history with rare race and road cars. Visits are limited and typically require advance booking.
- Recommended
Collier Museum at Government Center
Regional history museum covering Southwest Florida heritage, pioneer life, and local development through engaging exhibits.
- Must visit
Fifth Avenue South
Naples' best-known downtown street for strolling, people-watching, events, and polished Old Florida atmosphere.
- Must visit
Third Street South
Elegant shopping and walking district with historic charm, landscaping, and one of the city's most photogenic streetscapes.
- Must visit
Naples Beach
Classic Gulf beach known for white sand, sunsets, and easy pairing with downtown walks and pier views.
Grouper Sandwich
A Gulf Coast classic of fresh local grouper, usually grilled, blackened, or fried on a bun. It is a signature casual seafood meal in Southwest Florida.
- Gluten-free
Stone Crab Claws
Seasonal Florida stone crab claws are served chilled with mustard sauce. They are prized for sweet, firm meat and are strongly associated with Florida coastal dining.
Conch Fritters
A longtime South Florida and Florida Keys favorite also common in Naples, these are fried batter balls with chopped conch and spices, often served with dipping sauce.
Bha! Bha! Persian Bistro
An established Naples restaurant serving Persian and Mediterranean dishes in a lively, colorful setting. It is especially popular for distinctive flavors and hospitality.
Truluck's Ocean's Finest Seafood & Crab
An elegant seafood and steak restaurant known for high-quality crab, fresh seafood, and refined service. It fits a fine-dining night out in Naples.
USS Nemo Restaurant
A well-known upscale casual spot recognized for creative seafood dishes and Asian-influenced flavors. It is one of Naples' established local favorites.
United States Dollar
Prices are high, especially in peak season. Hotels and dining cost more than in many U.S. beach towns.
Average meal costs
- Budget
- USD 12-20 for casual food or takeout.
- Mid-range
- USD 25-45 per person at a mid-range restaurant.
- Fine dining
- USD 70+ per person at upscale restaurants.
- Coffee
- USD 4-7 for coffee at a cafe.
Tipping culture
Tip 18-20% at restaurants. Tip USD 1-2 per drink at bars, round up taxis, and tip hotel staff and valets.
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.
Cheap plane tickets from Chicago, IL to Naples, FL can start from as little as $82 (€67) when you book in advance. The average flight ticket price for Chicago, IL to Naples, FL is $172 (€141) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Chicago, IL to Naples, FL is 2h 47m to travel the 1135 miles (1827 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
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 9 direct flights a day from Chicago, IL to Naples, FL with American Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Chicago, IL to Naples, FL, you can count on American 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.
The cheapest month for a flight from Chicago, IL to Naples, FL is January.
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.
Since neither Chicago, IL nor Naples, FL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 1 h between Chicago, IL and Naples, FL all year round.
The best events to attend in Naples, FL include:
- Naples Winter Wine Festival, a premier charity wine auction featuring renowned vintners and gourmet dining experiences
- Naples Artcrafters Fine Art & Craft Show, an annual showcase of local artists and crafters displaying their unique creations
- Naples Seafood Festival, a vibrant celebration of fresh seafood with live music, cooking demonstrations, and family-friendly activities.
Some of the most interesting sights to explore in Naples, FL are:
- Naples Pier, a historic pier offering stunning views of the Gulf of Mexico and popular for fishing and sunset watching
- Naples Botanical Garden, a 170-acre garden showcasing diverse plant collections and ecosystems
- The Baker Museum, a contemporary art museum featuring a wide range of exhibitions and cultural events
- Clam Pass Park, a scenic beach park with a boardwalk through a mangrove forest leading to a beautiful beach
- Corkscrew Swamp Sanctuary, a wildlife sanctuary with a boardwalk trail through a pristine cypress forest, ideal for birdwatching and nature walks.
The best holidays to experience in Naples, FL include:
- Memorial Day, the unofficial start of summer with vibrant local events and warm weather
- Independence Day, festive fireworks and lively celebrations throughout the city
- Labor Day, a great time to enjoy the beach and local festivities as summer winds down.
The best things to do in Naples, FL include:
- Fifth Avenue South, a vibrant shopping and dining district with upscale boutiques and restaurants
- Naples Zoo at Caribbean Gardens, a zoo featuring animal exhibits, botanical gardens, and educational programs
- Delnor-Wiggins Pass State Park, a beautiful beach park perfect for swimming, sunbathing, and picnicking
- Tin City, a waterfront shopping and dining area with a charming, old Florida atmosphere
- Artis—Naples, a cultural complex offering performances, exhibitions, and educational programs.
The best season to visit Naples, FL is Spring or Fall. The best weather to explore Naples, FL is during April-June or September-October.
We recommend using the flight as it is the most popular way to get from Chicago, IL to Naples, FL among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 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.
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.
popular airports
Popular airports from Chicago, IL to Naples, FL
Chicago
Naples
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Shower
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
3 km
Car connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership
Lounge
- Lounges available, including United Club and American Airlines Admirals Club
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
Amenities at airport
WifiShoppingParkingDiningATMTaxisAccessibilityWCHotelLoungeLost and Found OfficeCar Rentalinformation
Distance to city center
4 kmCar connection
I-55, exit Cicero AveWifi
- Free Wi-Fi available throughout the airport
Shopping
- Shops are available in all concourses, including Hudson News and Chicago Market
Parking
- Parking available, short-term and long-term, approximately 2€ per hour
Dining
- Restaurants are available, including locations like Concourse A and B with options like Harry Caray's and Potbelly Sandwich Shop.
Taxis
- Available outside the terminal
Accessibility
- Ramps, toilets
WC
- Available throughout all concourses and terminals
Hotel
- Hotels are available within walking distance, such as the Hyatt Place Chicago Midway Airport.
Lounge
- Lounges available, including the USO Lounge for military personnel
Lost and Found Office
- Lost and Found located in the main terminal, near baggage claim
Car Rental
- Car rental services are available on-site, with companies like Avis, Budget, and Hertz
Public transit options for Midway International Airport
- CTA Orange Line, Midway station, 13 km
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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