Boston To Chicago Flights — from €125
Compare cheap flights from Boston 🇺🇸 to Chicago 🇺🇸. Real prices, daily refreshed from Aviasales.
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Other ways travelers describe this route — we cover all of them on this page:
🏨 Search Hotels in Chicago — Compare 100+ booking sites
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🎧 Self-Guided Audio Tours of Chicago
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🚕 Airport Transfer
🛡️ Travel Insurance from $4/day
📱 Get an eSIM (code FALLY20)
✈️ Flight Delayed? Claim up to €600
Boston → Barcelona Boston → Madrid Boston → Malaga Boston → Valencia Boston → Seville Boston → Ibiza Boston → Mallorca Boston → Tenerife Boston → Gran Canaria Boston → Lanzarote Boston → Bilbao Boston → Granada Boston → Lisbon Boston → Porto Boston → Faro Boston → Madeira Boston → Rome Boston → Milan Boston → Venice Boston → Florence Boston → Naples Boston → Palermo Boston → Catania Boston → Bologna Boston → Bari Boston → Verona Boston → Pisa Boston → Sardinia Boston → Paris Boston → 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 2026-04-13 · Real-time travel data · Affiliate disclosure: this page contains affiliate links — we earn a commission if you book.