Cheap Flights from Chicago to Madeira

Compare Chicago to Madeira flight deals

Find the cheapest month or even day of the year to fly to Madeira

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Flight deals from Chicago to Madeira

Looking for a cheap last-minute deal or the best return flight from Chicago to Madeira Airport? If you want to travel next month, return fares start from R 14,081. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Madeira

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Madeira flights are currently cheapest in August.

Chicago to Madeira: Alternative routes

Compare routes from Chicago to Madeira below. You may find an airport to fly into that's cheaper, faster, or easier than Madeira.

Chicago to Madeira: Flight information

The things to know before you go.
Cheapest flight foundR 5,255
Cheapest month to flyAugust

Finding cheap flights from Chicago to Madeira: Frequently asked questions

The best price we found for a return flight from Chicago to Madeira is R 12,257. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Madeira. But we found flights with one stop from R 12,257.
As of June 2026, there are no flights flying from Chicago to Madeira.
The cheapest month to fly from Chicago to Madeira is usually January.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Madeira Airport on Wednesday, 20 January 2027.
No airlines currently offer direct flights between Chicago and Madeira Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Madeira but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Madeira is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Madeira is TAP Air Portugal .

Flying from Chicago to Madeira Airport (FNC): What you need to know

  • Madeira is six hours ahead of Chicago. Madeira Airport is located in Madeira, which follows the UTC+0 timezone.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your flight from Chicago to FNC.

  • If you're going away during a popular month like July, be at the airport even earlier. You'll want to arrive up to four hours before international flights and two hours ahead of domestic departures. Check-in and security lines are longer during peak periods like Thanksgiving and Christmas.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • We make it a piece of cake to find cheap flights from Chicago to FNC that include a stopover. To explore your options departing from Chicago O'Hare International Airport (ORD), uncheck 'Direct flights only.' Then, simply select a flight that has a stop long enough to tour the city of your choice. Major stopovers between ORD and FNC include:

    • New York John F. Kennedy International Airport (JFK)

    • Boston Logan International Airport (BOS)

    • Toronto Pearson International Airport (YYZ)

  • ORD is around 27 kilometres from central Chicago. If you're catching a taxi, driving or ride-sharing from the centre, it'll take you 30 minutes or so to get there, depending on traffic. If you're taking public transport, expect the journey time to be around 45 minutes.

  • Catching an early flight from Chicago to Madeira Airport? Avoid the hassle of rushing to the terminal (and enjoy a little extra shut-eye) by staying at one of these stays close to Chicago O'Hare International Airport:

  • Of all flights leaving Chicago O'Hare International Airport, 70% touch down on time at their destination.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Fit a stopover into your itinerary at Boston Logan International Airport (BOS). It's a popular transfer point for flights from Chicago to Madeira Airport (FNC) leaving Chicago Midway International Airport.

  • You can reach MDW from central Chicago in about 25 minutes by car (depending on traffic conditions). The ride by public transport takes roughly 30 minutes to cover the 16 kilometres or so.

  • Start your holiday sooner with an extra night away from home. Before your Chicago to FNC flight, stay in one of these hotels close to Chicago Midway International Airport:

  • When it comes to keeping flights punctual, Chicago Midway International Airport has an on-time arrival rate of 76%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 145 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 40 minutes. If you're planning to take public transport, expect a journey time of around 2 hours.

  • Wake up, take it easy and still make your Chicago to Madeira Airport flight with time to spare. These accommodation options near Chicago Rockford International Airport make it a breeze to get to the terminal if you're jetting off early:

  • Airports have an on-time performance rating that measures how often flights touch down within the expected time frame. At RFD, that figure is 71%.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Madeira Airport (FNC)

Getting from Madeira Airport (FNC) to central Madeira

  • Central Madeira is around 18 kilometres from Madeira Airport and takes about 25 minutes to reach by car. Look into how to get from the airport to the city, whether that's with a taxi, car hire or ride-share.

  • It takes around 45 minutes to get there using public transport.

How to find the cheapest flights from Chicago to Madeira Airport (FNC)

  • R 5,255 is the best price for a one-way ticket from Chicago to Madeira Airport. A return flight starts from R 12,257. These prices may change depending on availability and demand.

  • Don't leave everything to the last moment. You're more likely to find cheap flights from Chicago to FNC if you book in advance. Airlines often have some great early bird discounts.

  • Affordable Chicago to Madeira Airport tickets are easier to find when you have flexibility in your schedule. Use the 'Whole month' search tool to compare fares across every month and then fly out on the cheapest day.

  • Locking in a cheap plane ticket from Chicago to FNC is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll notify you when the price has dropped.

  • Tailor your flights using filters. Select your ideal departure and arrival times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' flights from Chicago to Madeira Airport.

The best time to fly from Chicago to Madeira Airport (FNC)

  • August is when most people book flights from Chicago to Madeira Airport (FNC). Plan your visit to Madeira in January for a quieter experience.

  • Before locking in your Chicago to FNC plane ticket, consider what kind of weather works for you. August is the warmest month in Madeira, with temperatures ranging from 16ºC (61ºF) to 25ºC (77ºF).

  • If you'd rather travel in cooler conditions, look for a cheap ticket from Chicago to Madeira Airport in February when temperatures are between 9ºC (48ºF) and 16ºC (61ºF).

More about Madeira

  • Once you've booked your flight from Chicago to Madeira Airport, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Madeira:

  • There are so many things to do and see in this city, it can be hard to know where to begin. Madeira Island, Miradouro de Santa Luzia and Monte Palace Madeira are top sights which should be on any well-planned Madeira itinerary.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.