Cheap Flights from Chicago to Madeira
Compare cheap flights from Chicago 🇺🇸 to Madeira 🇵🇹. Real prices, daily refreshed from Aviasales.
Live price data temporarily unavailable for this route. Search current fares directly →
| Currency | EUR (€) |
| Language | Portuguese |
| Power plug | Type C/F |
| Tipping | 5-10% |
| Emergency | 112 |
🏨 Search Hotels in Madeira — Compare 100+ booking sites
🚗 Rent a Car in Madeira — 800+ rental brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours of Madeira
🎫 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 → 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 → Madeira Paris → Madeira Amsterdam → Madeira Brussels → Madeira Frankfurt → Madeira Munich → Madeira Berlin → Madeira Hamburg → Madeira Zurich → Madeira Geneva → Madeira Vienna → Madeira Dublin → Madeira Madrid → Madeira Barcelona → Madeira Lisbon → Madeira Porto → Madeira Rome → Madeira Milan → Madeira Naples → Madeira Athens → Madeira Copenhagen → Madeira Stockholm → Madeira Oslo → Madeira Helsinki → Madeira Reykjavik → Madeira Warsaw → Madeira Krakow → Madeira Prague → Madeira Budapest → Madeira Bucharest → Madeira
Updated 2026-04-14 · Real-time travel data · Affiliate disclosure: this page contains affiliate links — we earn a commission if you book.
The Chicago to Madeira flight takes approximately 4–9 hours depending on routing. Total journey time including check-in and airport transfers adds 2–3 hours. Filter search results by total journey time, not just fare, to find the most efficient routing.
January, february, and november typically offer the lowest fares, often 25–45% below peak-season prices. Shoulder season — April through May and September through October — balances value with excellent travel conditions. Avoid school holiday windows, when demand drives fares sharply higher.
Book 3–5 weeks ahead for the best price and seat availability. Fares typically rise sharply inside 14 days of departure. Searching on Tuesday or Wednesday mornings returns 10–15% lower fares than weekend searches on average.
Direct nonstop service may be limited on this route. Most itineraries connect through a major hub. Check current airline schedules as nonstop routes are added and removed seasonally.
Set a fare alert for the route and search ±3 days around your target travel dates. Compare fares from nearby airports — a short drive can unlock significantly lower base fares. Self-connecting through a separate booking can beat bundled itinerary prices by 20–30%, though this carries risk if your first segment is delayed.