Flights From Chicago To Madrid — from
Compare cheap flights from Chicago 🇺🇸 to Madrid 🇪🇸. Real prices, daily refreshed from Aviasales.
Cheapest month: 2027-03 at €668. Highest: €988. Tap a bar to jump to that month's fares ↓
Pre-season March cuts fares 17% below the yearly average - before peak beach demand arrives. July is the peak month (23% above average).
Live cached prices from Aviasales. Pick a month, compare, book in one click.
| Currency | EUR (€) |
| Language | Spanish |
| Power plug | Type C/F |
| Tipping | 5-10% |
| Emergency | 112 |
Other ways travelers describe this route — we cover all of them on this page:
🏨 Search Hotels in Madrid — Compare 100+ booking sites
🚗 Rent a Car in Madrid — 800+ rental brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours of Madrid
🎫 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 → 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 → Madrid Paris → Madrid Amsterdam → Madrid Brussels → Madrid Frankfurt → Madrid Munich → Madrid Berlin → Madrid Hamburg → Madrid Zurich → Madrid Geneva → Madrid Vienna → Madrid Dublin → Madrid Barcelona → Madrid Lisbon → Madrid Porto → Madrid Rome → Madrid Milan → Madrid Naples → Madrid Athens → Madrid Copenhagen → Madrid Stockholm → Madrid Oslo → Madrid Helsinki → Madrid Reykjavik → Madrid Warsaw → Madrid Krakow → Madrid Prague → Madrid Budapest → Madrid Bucharest → Madrid Sofia → Madrid
Updated 2026-05-25 · Real-time travel data · Affiliate disclosure: this page contains affiliate links — we earn a commission if you book.