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Cheap flight tickets 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? Find the lowest prices on one-way and return tickets right here.
Madeira.RM2,014 per passenger.Departing Sun, 19 Apr, returning Wed, 29 Apr.Return flight with Iberia.Outbound indirect flight with Iberia, departs from Chicago O'Hare International on Sun, 19 Apr, arriving in Madeira.Inbound indirect flight with Iberia, departs from Madeira on Wed, 29 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,014, select.
Madeira.RM2,174 per passenger.Departing Sun, 8 Mar, returning Tue, 17 Mar.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Sun, 8 Mar, arriving in Madeira.Inbound indirect flight with TAP Air Portugal, departs from Madeira on Tue, 17 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,174, select.
Madeira.RM2,221 per passenger.Departing Wed, 18 Nov, returning Wed, 25 Nov.Return flight with British Airways.Outbound indirect flight with British Airways, departs from Chicago O'Hare International on Wed, 18 Nov, arriving in Madeira.Inbound indirect flight with British Airways, departs from Madeira on Wed, 25 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,221, select.
Madeira.RM2,371 per passenger.Departing Fri, 24 Apr, returning Fri, 1 May.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Fri, 24 Apr, arriving in Madeira.Inbound indirect flight with TAP Air Portugal, departs from Madeira on Fri, 1 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,371, select.
Madeira.RM2,464 per passenger.Departing Thu, 24 Sep, returning Thu, 1 Oct.Return flight with KLM.Outbound indirect flight with KLM, departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Madeira.Inbound indirect flight with KLM, departs from Madeira on Thu, 1 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,464, select.
Madeira.RM2,720 per passenger.Departing Wed, 16 Sep, returning Wed, 23 Sep.Return flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departs from Chicago O'Hare International on Wed, 16 Sep, arriving in Madeira.Inbound indirect flight with TAP Air Portugal, departs from Madeira on Wed, 23 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,720, select.
Madeira.RM2,809 per passenger.Departing Sun, 3 May, returning Sat, 9 May.Return flight with British Airways.Outbound indirect flight with British Airways, departs from Chicago O'Hare International on Sun, 3 May, arriving in Madeira.Inbound indirect flight with British Airways, departs from Madeira on Sat, 9 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM2,809, select.
Madeira.RM3,160 per passenger.Departing Thu, 16 Jul, returning Thu, 23 Jul.Return flight with KLM.Outbound indirect flight with KLM, departs from Chicago O'Hare International on Thu, 16 Jul, arriving in Madeira.Inbound indirect flight with KLM, departs from Madeira on Thu, 23 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From RM3,160, select.

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 April.
Mar
from RM2,174
Apr
from RM2,014
May
from RM2,809
Jun
from RM3,798
Jul
from RM3,160
Aug
from RM3,318
Sep
from RM2,720
Oct
Find prices
Nov
from RM2,221
Dec
Find prices
Jan
Find prices
Feb
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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.

Madeira

13km from central Madeira
ClosestCheapest
from RM2,014
Search flights

Porto Santo

70km from central Madeira
Search flights

Chicago to Madeira: Flight information

The things to know before you go.
Cheapest flight foundRM2,014
Cheapest month to flyApril

Finding cheap flights from Chicago to Madeira: Frequently asked questions

The best price we found for a return flight from Chicago to Madeira is RM2,014. 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 RM2,014.
As of March 2026, there are no flights flying from Chicago to Madeira.
The cheapest month to fly from Chicago to Madeira is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Madeira Airport on Sunday, 19 April 2026.
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 Iberia .

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

  • Chicago is home to two main airports that set the stage for your next getaway. Explore your options for booking a flight from Chicago to Madeira Airport (FNC) heading out from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • Madeira Airport is located in Madeira. The city follows the UTC+0 timezone and is five hours ahead of Chicago.

  • Your flight from Chicago to FNC won't wait if you're running late, so get to the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • Heading away during a peak period like public or school holidays? Expect longer queues at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours ahead of domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • A stopover is the ideal opportunity to break up your trip and possibly even explore another city. When searching for cheap flights from Chicago to FNC leaving from O'Hare International Airport (ORD), uncheck the 'Direct flights only' box to find out where you can stop along the way. Your journey might pause in:

    • John F. Kennedy International Airport (JFK)

    • Logan International Airport (BOS)

    • Pearson International Airport (YYZ)

  • The journey from central Chicago to ORD takes around 55 minutes on public transport. If you ride-share, drive or grab a cab, you'll cover the 40 kilometres in 35 minutes or so, depending on traffic.

  • Want a leisurely start to your trip? Stay near O'Hare International Airport. Whether you have an early flight from Chicago to Madeira Airport or just don't want to be rushed, these hotels offer the perfect solution:

  • 74.85% of flights that depart O'Hare International Airport reach their destination on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Break up your flight from Chicago to Madeira Airport with a stop at Logan International Airport (BOS). One of the main stopovers between Chicago Midway International Airport and FNC, it's a good opportunity to recharge before the next leg of your journey.

  • MDW is around 19 kilometres from central Chicago. It takes 20 minutes or so to get to the airport driving from the city centre. Public transport takes approximately 45 minutes.

  • Want to enjoy an extra night away before boarding your Chicago to FNC flight? Kick back in a hotel near Chicago Midway International Airport before your trip officially starts. These stays are calling your name:

  • Chicago Midway International Airport has an on-time performance rate of 77.88%. This figure gives an insight into how often flights that leave from this airport arrive on schedule.

  • The street address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey time to RFD from central Chicago is around 4 hours 15 minutes by public transport. If you're in a car, it'll take you about 1 hour 25 minutes to cover the 137 kilometres or so.

  • Make catching an early Chicago to Madeira Airport flight the easiest part of your trip. Stay at one of these hotels close to Chicago Rockford International Airport and head to your check-in counter with time to spare:

  • The on-time performance record of RFD is 76.19%. In other words, that's how often flights that depart this airport reach their final stop as planned.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Madeira Airport (FNC)

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Chicago to Madeira Airport. Book one of these accommodation options near FNC instead:

  • Grab a Madeira Airport rental car and explore Madeira and beyond with your own set of wheels. Way 2 azores, Surprice and Magic Islands Rent A Car are top outlets to choose from here.

  • To lock in the lowest price, book your ride around one week ahead of your Chicago to Madeira Airport flight.

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

  • The cheapest price we've found for a one-way ticket from Chicago to Madeira Airport is RM1,640. For a return flight on this route, the best price is RM2,014. Depending on when you want to go and the availability, these fares could change.

  • Booking in advance is often the key to finding a cheap flight from Chicago to FNC. Fares tend to rise as seats fill up, so the closer your departure date, the more expensive your ticket may be.

  • Cheap 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 each month and then pick the cheapest day.

  • Finding a cheap plane ticket from Chicago to FNC is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when the price has dropped.

  • Filters make it easier to land a deal on your flight from Chicago to Madeira Airport. Pick the departure times, airlines and number of stops that line up with your plans. Then sort the results by 'Cheapest' to find the most affordable option fast.

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

  • It's time to work out when to book your flight from Chicago to Madeira Airport (FNC). July is the busiest month to visit Madeira. If you like your getaways a little more chill, go in April.

  • Lock in a Chicago to FNC plane ticket departing in August if you're eager to explore the city during its warmest month. You can expect temperatures in Madeira to range from 16ºC (61ºF) to 25ºC (77ºF).

  • February sees temperatures of between 9ºC (48ºF) and 16ºC (61ºF). Search for cheap tickets from Chicago to Madeira Airport around that time if you'd rather travel in cooler conditions.

More about Madeira

Plan the rest of your trip from Chicago to Madeira

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.