Find and Compare the Cheapest Ways to Fly from Naples to Chicago

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

Based on typical seasonal demand, February, September, and January tend to offer the lowest fares on this route, with estimated round-trip prices starting around $570. Live prices change daily, so run a search for your exact dates.

Naples and Chicago are about 4,930 miles apart. A nonstop flight takes roughly 10h 25m, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.

This route arrives at O'Hare International Airport (ORD). Your search results also show nearby airports when they offer a cheaper or faster option.

For this route, booking about 2 to 6 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.