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Journey information
Overview: Chicago, IL to Naples, FL flight
USAUSA
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 $46 (€38) |
Flights per day 30 |
Direct flights 4 |
Fastest flight 2h 49m |
Cheapest month to travel July |
First flight 05:00 |
Last flight 22:05 |
Key Takeaways
Train Ticket Prices
- Budget Options: Train tickets from Chicago, IL to Naples, FL start from as low as $46 (€38) if booked well in advance.
- Standard Fares: Typically, trains cost $164 (€134) depending on the train type and class.
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 Nov 07
Cheapest price
$151
Average price
$151
Fastest journey
2 h 55 m
Average duration
2 h 55 m
Flights per day
1
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 $151 if you buy it on the day, but the cheapest tickets can be found for only $151.
Fast flights
Of the 1 flights that leave Chicago, IL for Naples, FL onFri, Nov 07, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Nov 07 the direct flights cover the 1827 km distance in an average of 2 h 55 m but if you time it right, some flights will get you there in just 2 h 55 m .
On Fri, Nov 07 the longest flights will take 2 h 55 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.
10:31PM2h55
Chicago, IL01:26AMNaples, FL
$1511One-way
0 transfers
10:31PM2h55
Chicago, IL01:26AMNaples, FL
$1511One-way
0 transfers
Travel Information
Compare flight and bus 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 €38. 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 €38, and a bus costs an average of €179.
Distance: 1135 miles (1827 km)
Compare flight with
Most popular Flight | Bus |
|---|---|
€134 Average price Cheapest | €179 Average price |
5h 49m Average total duration Fastest 2h 49m Onboard + 3h 0m Additional time* | 37h 0m Average total duration 36h 30m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Live departures
Chicago, IL to Naples, FL flight times
The table below shows live departures for Chicago, IL to Naples, FL flights for today, Thursday, November 6. You can also manually refresh the results below to see updated flight journeys.
Last updated at 8:41 PM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 AA2840 · AA1450 | 8:50 PM O'Hare International Airport | 8h09 | 4:59 AM Southwest Florida International Airport | 1 transfer | |
| AA2202 · AA2474 | 8:54 PM O'Hare International Airport | 6h15 | 3:09 AM Southwest Florida International Airport | 1 transfer | |
 UA2095 · UA2682 | 9:43 PM O'Hare International Airport | 6h32 | 4:15 AM Southwest Florida International Airport | 1 transfer | |
| UA3438 · UA1100 | 9:55 PM O'Hare International Airport | 18h09 | 4:04 PM Southwest Florida International Airport | 1 transfer | |
| AA2576 · AA1780 | 10:05 PM O'Hare International Airport | 7h22 | 5:27 AM Southwest Florida International Airport | 1 transfer | |
| UA1946 | 10:15 PM O'Hare International Airport | 3h01 | 1:16 AM Southwest Florida International Airport | 0 transfersDirect | |
 G4886 | 10:33 PM Midway International Airport | 2h48 | 1:21 AM Punta Gorda Airport | 0 transfersDirect | |
| AA1876 · AA1780 | 11:30 PM O'Hare International Airport | 5h57 | 5:27 AM Southwest Florida International Airport | 1 transfer | |
| Friday, November 7 | |||||
| UA2652 · UA1100 | 12:20 AM O'Hare International Airport | 15h44 | 4:04 PM Southwest Florida International Airport | 1 transfer | |
| AA894 · AA1780 | 12:35 AM O'Hare International Airport | 4h52 | 5:27 AM Southwest Florida International Airport | 1 transfer | |
| AA648 | 1:15 AM O'Hare International Airport | 3h00 | 4:15 AM Southwest Florida International Airport | 0 transfersDirect | |
| UA1641 · UA1100 | 1:35 AM O'Hare International Airport | 14h29 | 4:04 PM Southwest Florida International Airport | 1 transfer | |
| UA1023 · UA1251 | 3:10 AM O'Hare International Airport | 17h50 | 9:00 PM Southwest Florida International Airport | 1 transfer | |
| UA3639 · UA1100 | 3:35 AM O'Hare International Airport | 12h29 | 4:04 PM Southwest Florida International Airport | 1 transfer | |
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 flight or bus
Compare flight and bus 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.
Fri
Nov 07
Nov 07
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Nov 08
Nov 08
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Nov 13
Nov 13
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 $46 (€38). 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 53m
Cheapest Price
$481 (€392)
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
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.
The earliest flight from Chicago, IL to Naples, FL leaves at 5: 15AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Naples, FL leaves at 7: 58PM.
The cheapest month to travel from Chicago, IL to Naples, FL by plane is December.
Yes, you can take a bus to Naples, FL from Chicago, IL.
Since neither Chicago, IL nor Naples, FL are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. 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.
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 seasons to visit Naples, FL are Spring or Fall. The best weather to explore Naples, FL is during April-June or September-October.
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.
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.
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
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Most popular flights to and from Naples, FL and Chicago, IL
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