Chicago To Boston Flights — from €129
Compare cheap flights from Chicago 🇺🇸 to Boston 🇺🇸. 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 Boston — Compare 100+ booking sites
🚗 Rent a Car in Boston — 800+ rental brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours of Boston
🎫 Skip-the-Line Tickets
🚕 Airport Transfer
🛡️ Travel Insurance from $4/day
📱 Get an eSIM (code FALLY20)
✈️ Flight Delayed? Claim up to €600
Chicago → Barcelona Chicago → Madrid Chicago → Malaga Chicago → Valencia Chicago → Seville Chicago → Ibiza Chicago → Mallorca Chicago → Tenerife Chicago → Gran Canaria Chicago → Lanzarote Chicago → Bilbao Chicago → Granada Chicago → Lisbon Chicago → Porto Chicago → Faro Chicago → Madeira Chicago → Rome Chicago → Milan Chicago → Venice Chicago → Florence Chicago → Naples Chicago → Palermo Chicago → Catania Chicago → Bologna Chicago → Bari Chicago → Verona Chicago → Pisa Chicago → Sardinia Chicago → Paris Chicago → Nice
London → Boston Paris → Boston Amsterdam → Boston Brussels → Boston Frankfurt → Boston Munich → Boston Berlin → Boston Hamburg → Boston Zurich → Boston Geneva → Boston Vienna → Boston Dublin → Boston Madrid → Boston Barcelona → Boston Lisbon → Boston Porto → Boston Rome → Boston Milan → Boston Naples → Boston Athens → Boston Copenhagen → Boston Stockholm → Boston Oslo → Boston Helsinki → Boston Reykjavik → Boston Warsaw → Boston Krakow → Boston Prague → Boston Budapest → Boston Bucharest → Boston
Updated 2026-04-14 · Real-time travel data · Affiliate disclosure: this page contains affiliate links — we earn a commission if you book.