Naples to Chicago (NAP-ORD): nonstop upgrade & award space

American Airlines flies the NAP to ORD nonstop about 7 times a week. With American Airlines flying most of the schedule, the long-haul premium cabin opens when that one carrier decides it does, which is why the calendar matters more than the search. 2LNR tracks confirmed upgrade and award space on American Airlines, on every NAP to ORD departure, so you know which flights have space before you book.

Schedule last confirmed . Departure times come from 2LNR's schedule data; confirm with the airline before you book.

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7
Nonstop flights a week
4,933 mi
Nonstop distance
Free
To get started

Naples to Chicago flight schedule

Scheduled nonstop departures for NAP to ORD, last checked against our schedule feed on September 6, 2026. Airlines retime and cancel flights, so confirm with the airline before you book.

Schedule data dated .

Scheduled nonstop departures from Naples (NAP) to Chicago (ORD)
Date Flight Airline Departs NAP Arrives ORD Duration Aircraft
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788
AA 181American Airlines15:0018:5510h 55m788

Showing all 7 scheduled NAP to ORD departures across the next 7 days with service. Later dates are on the interactive map.

Departure and arrival times are local at their own airport, so an arrival can fall on a different local date than the departure; the duration column is the true elapsed flying time. A dash means the airline has not filed that value in the schedule data we hold. Aircraft are IATA equipment codes as filed, and can change up to departure.

See every NAP to ORD date on the interactive map

Confirmed upgrade & award space on NAP to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Naples to Chicago to see which departures have space, the next 14 days free on every product and the full horizon on Pro.

See real availability

Confirmed upgrade and award seats on each NAP to ORD departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See NAP to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Naples to Chicago nonstop

Carriers operating NAP to ORD nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

See NAP to ORD on the interactive map →

Frequently asked questions about NAP to ORD

How far is Chicago from Naples?
NAP to ORD covers about 4,933 miles nonstop. Flight times vary by aircraft and season; the schedule table on this page lists each scheduled departure with its own times.
Which airlines fly nonstop from NAP to ORD?
American Airlines is currently the only airline flying NAP to ORD nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from NAP to ORD?
About 7 nonstop flights a week run between Naples and Chicago in the current schedule, operated by American Airlines. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
What time do flights from NAP to ORD depart?
In the next 7 days with service, every scheduled NAP to ORD nonstop leaves at 15:00 local time at Naples. The schedule table on this page lists each departure by date.
How do I check upgrade or award availability on NAP to ORD?
Open the NAP to ORD route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines, the next 14 days free and the full horizon on Pro. On Pro you can also set an alert on the route and 2LNR notifies you when space opens.

Never miss NAP to ORD upgrade or award space

See what is open by date on this route, the next 14 days free on every product and the full horizon on Pro.

Get started free