Cheap Flights from New York JFK to
Compare cheap flights from New York JFK 🇺🇸 to Chicago 🇺🇸. Real prices, daily refreshed from Aviasales.
Cheapest month: 2026-09 at €153. Highest: €327. Tap a bar to jump to that month's fares ↓
September is the sweet spot on this route. Summer tourists have left, locals are back at work, and fares dip 23% below the yearly average. August is the month to avoid (65% above average).
Live cached prices from Aviasales. Pick a month, compare, book in one click.
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New York JFK → Barcelona New York JFK → Madrid New York JFK → Malaga New York JFK → Valencia New York JFK → Seville New York JFK → Ibiza New York JFK → Mallorca New York JFK → Tenerife New York JFK → Gran Canaria New York JFK → Lanzarote New York JFK → Bilbao New York JFK → Granada New York JFK → Lisbon New York JFK → Porto New York JFK → Faro New York JFK → Madeira New York JFK → Rome New York JFK → Milan New York JFK → Venice New York JFK → Florence New York JFK → Naples New York JFK → Palermo New York JFK → Catania New York JFK → Bologna New York JFK → Bari New York JFK → Verona New York JFK → Pisa New York JFK → Sardinia New York JFK → Paris New York JFK → Nice
London → Chicago Paris → Chicago Amsterdam → Chicago Brussels → Chicago Frankfurt → Chicago Munich → Chicago Berlin → Chicago Hamburg → Chicago Zurich → Chicago Geneva → Chicago Vienna → Chicago Dublin → Chicago Madrid → Chicago Barcelona → Chicago Lisbon → Chicago Porto → Chicago Rome → Chicago Milan → Chicago Naples → Chicago Athens → Chicago Copenhagen → Chicago Stockholm → Chicago Oslo → Chicago Helsinki → Chicago Reykjavik → Chicago Warsaw → Chicago Krakow → Chicago Prague → Chicago Budapest → Chicago Bucharest → Chicago
Updated 2026-04-20 · Real-time travel data · Affiliate disclosure: this page contains affiliate links — we earn a commission if you book.
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Primary sources over aggregators. Prices from airline/rail/hotel APIs; seasonality from tourism boards; safety stats from national archives where possible.