--- title: "Naples (NAP) to Chicago (ORD) flights: who flies it" description: "American Airlines flies nonstop from NAP to ORD, about 2 flights a week. See confirmed upgrade and award space by date on 2LNR, the next 14 days free." canonical: "https://2lnr.com/routes/nap-ord" url: "https://2lnr.com/routes/nap-ord.md" date_modified: "2026-10-18T05:10:47Z" --- # Naples to Chicago (NAP-ORD): nonstop upgrade & award space American Airlines flies nonstop from Naples (NAP) to Chicago (ORD) just twice a week. In the timetable below it flies as AA 181, scheduled at 10h 50m to 10h 55m for the 4,933 miles. 2LNR checks confirmed upgrade and award space on American Airlines flights on this route, so you can see which departures have space before you book. Schedule last confirmed October 18, 2026. Departure times come from 2LNR's schedule data; confirm with the airline before you book. Updated October 23, 2026. See NAP to ORD on the interactive map [Get started free](https://2lnr.com/login) 2 Flights a week, 4-week average 10h 50m to 10h 55m Scheduled flight time 4,933 mi Nonstop distance Free To get started ## Naples to Chicago flight schedule Scheduled nonstop departures for NAP to ORD starting October 23, 2026, last checked against our schedule feed on October 18, 2026. Airlines retime and cancel flights, so confirm with the airline before you book. Scheduled nonstop departures from Naples (NAP) to Chicago (ORD) | Date | Flight | Airline | Departs NAP | Arrives ORD | Duration | Aircraft | | :--- | :--- | :--- | :--- | :--- | :--- | :--- | | Fri, Oct 23 | AA 181 | American Airlines | 15:00 | 18:50 | 10h 50m | [Boeing 787-8 Dreamliner](https://2lnr.com/seatmaps/aa/787-8.md) | | Sat, Oct 24 | AA 181 | American Airlines | 15:00 | 18:50 | 10h 50m | Boeing 787-8 Dreamliner | | Sat, May 8 | AA 181 | American Airlines | 15:00 | 18:55 | 10h 55m | Boeing 787-8 Dreamliner | | Sun, May 9 | AA 181 | American Airlines | 15:00 | 18:55 | 10h 55m | Boeing 787-8 Dreamliner | | Mon, May 10 | AA 181 | American Airlines | 15:00 | 18:55 | 10h 55m | Boeing 787-8 Dreamliner | | Tue, May 11 | AA 181 | American Airlines | 15:00 | 18:55 | 10h 55m | Boeing 787-8 Dreamliner | | Wed, May 12 | AA 181 | American Airlines | 15:00 | 18:55 | 10h 55m | Boeing 787-8 Dreamliner | Showing all 7 scheduled NAP to ORD departures across 7 days with service, starting October 23, 2026. 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 hasn't filed that value in the schedule data we hold. Aircraft are the equipment the airline filed, named where the code pins down one type and shown as the family or the bare code where it doesn't. Swaps can happen up to departure. See every NAP to ORD date on the interactive map ## Aircraft on the Naples to Chicago nonstop American Airlines flies the [Boeing 787-8 Dreamliner](https://2lnr.com/seatmaps/aa/787-8.md) on every departure in the schedule table on this page. Each linked aircraft page shows where that airline schedules it. Airlines can swap aircraft up to departure. ## 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. American Airlines award space was open on 5 of the 6 Naples to Chicago departure dates from October 19 to November 1 that 2LNR checked in the 7 days to October 19, 2026. ### See real availability Confirmed upgrade or award seats by date on the NAP to ORD departures 2LNR tracks, checked against live inventory so you know what's open before you book. ### Set an alert Premium inventory turns over fast. Watch this route on Pro and 2LNR notifies you when space appears on a date you're 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date. - [American Airlines (AA) route map](https://2lnr.com/routes/airlines/aa.md)\ [The aircraft AA flies](https://2lnr.com/seatmaps/aa.md) See NAP to ORD on the interactive map → ## Frequently asked questions about NAP to ORD **How long is the flight from Naples (NAP) to Chicago (ORD)?** Scheduled flight times from Naples (NAP) to Chicago (ORD) run from 10h 50m to 10h 55m across the departures in the schedule table on this page. The nonstop covers about 4,933 miles, and airlines adjust scheduled times by season, so confirm with the airline before you book. **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 often does NAP to ORD operate?** The NAP to ORD nonstop currently runs twice a week, on American Airlines. Thin schedules like this change by season, and on Pro an alert will catch anything added. **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. **Which flights operate NAP to ORD nonstop?** American Airlines flies AA 181 nonstop from Naples (NAP) to Chicago (ORD), the only flight number in the schedule table on this page. The table lists each date with its departure and arrival times and aircraft. **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. Flying the other way? See [ORD to NAP upgrade and award space](https://2lnr.com/routes/ord-nap.md). Award seats rather than schedules? See [American Airlines award availability](https://2lnr.com/awards/aa.md). Looking beyond this route? See [every route from Naples (NAP)](https://2lnr.com/routes/nap.md), or [every route from Chicago (ORD)](https://2lnr.com/routes/ord.md). Nonstops to Chicago (ORD) from other airports within 150 miles of Naples (NAP): - [Rome (FCO) to Chicago (ORD)](https://2lnr.com/routes/fco-ord.md), 125 miles from NAP Distances are great-circle between the airports, not driving distance. - [How American upgrades clear](https://2lnr.com/about/aa/upgrades.md) - [How to read award availability by date](https://2lnr.com/guides/award-availability.md) ## Never miss NAP to ORD upgrade or award space See what's open by date on this route, the next 14 days free on every product and the full horizon on Pro. [Get started free](https://2lnr.com/login)