$283 Find Cheap Flights from Chicago to Madeira

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Madeira departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Madeira

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Madeira, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Madeira, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Madeira Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Madeira that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Madeira

Thu, Jan 15 - Sat, Jan 24
Scandinavian Airlines Logo
7:20 pm - 1:45 pmORD-FNC
36h 25m2 stops
Scandinavian Airlines Logo
2:35 pm - 4:55 pmFNC-ORD
32h 20m2 stops
$472Scandinavian Airlines
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Fri, Dec 5 - Sat, Dec 13
Scandinavian Airlines Logo
7:20 pm - 3:20 pmORD-FNC
14h 00m1 stop
Scandinavian Airlines Logo
4:10 pm - 4:45 pmFNC-ORD
30h 35m1 stop
$482Scandinavian Airlines
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Tue, Dec 2 - Thu, Dec 11
British Airways Logo
5:10 pm - 3:05 pmORD-FNC
15h 55m1 stop
British Airways Logo
5:10 pm - 1:50 pmFNC-ORD
26h 40m1 stop
$487British Airways
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Fri, Dec 5 - Sat, Dec 13
Scandinavian Airlines Logo
7:20 pm - 3:20 pmORD-FNC
14h 00m1 stop
Scandinavian Airlines Logo
4:10 pm - 4:45 pmFNC-ORD
30h 35m1 stop
$489Scandinavian Airlines
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Thu, Nov 27 - Thu, Dec 4
KLM Logo
1:25 pm - 5:10 pmORD-FNC
21h 45m2 stops
KLM Logo
10:20 am - 2:20 pmFNC-ORD
34h 00m1 stop
$521KLM
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Thu, Nov 27 - Thu, Dec 4
KLM Logo
1:25 pm - 5:10 pmORD-FNC
21h 45m2 stops
KLM Logo
10:20 am - 2:20 pmFNC-ORD
34h 00m1 stop
$527KLM
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Wed, Dec 3 - Tue, Dec 16
TAP AIR PORTUGAL Logo
7:10 pm - 1:50 pmORD-FNC
12h 40m1 stop
TAP AIR PORTUGAL Logo
4:10 am - 3:00 pmFNC-ORD
16h 50m1 stop
$532TAP AIR PORTUGAL
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Thu, Dec 4 - Mon, Dec 15
British Airways Logo
9:45 pm - 11:20 amORD-FNC
31h 35m1 stop
British Airways Logo
12:25 pm - 6:45 pmFNC-ORD
36h 20m1 stop
$538British Airways
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Wed, Oct 29 - Wed, Nov 5
TAP AIR PORTUGAL Logo
8:10 pm - 5:10 pmORD-FNC
16h 00m1 stop
TAP AIR PORTUGAL Logo
7:50 am - 3:00 pmFNC-ORD
13h 10m1 stop
$565TAP AIR PORTUGAL
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Sat, Mar 7 - Sun, Mar 15
Iberia Logo
4:45 pm - 10:30 amORD-FNC
11h 45m1 stop
Iberia Logo
11:10 am - 10:28 pmFNC-ORD
40h 18m2 stops
$574Iberia
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Booking Insights

KAYAK's insights & trends for Chicago to Madeira flights

Get data-powered insights and trends into flights from Chicago to Madeira to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Madeira?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Madeira, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Madeira is November, when tickets cost $607 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,455 and $1,200 respectively.

Good to know

Low seasonFebruary
Cheapest flight$252
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago to Funchal

FAQs - booking Madeira flights

  • How does KAYAK find such low prices on flights from Chicago to Madeira?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Madeira.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Madeira?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Madeira is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Madeira?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Madeira with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Madeira?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Madeira up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Madeira?

    The cheapest time of day to fly to Madeira is generally at night, when round-trip flights cost $786 on average. Morning departures are around 12% cheaper than evening flights, on average. The most expensive time of day to fly to Madeira is generally in the evening, which is peak travel time and where the average cost of a ticket is $1,073.

Reviews of the top airline flying from Chicago to Madeira

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Madeira. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Madeira? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
TAP AIR PORTUGALOverall score based on 2009 reviews
7.1Comfort
7.8Crew
7.0Boarding
6.3Entertainment
6.2Food
Airline reviews

Bad boarding, threat to force bag check mid journey, lines, late, buses, more waiting awful end to end.

2.0 MediocreAnonymous, Oct 2025LHR - LIS
Read more TAP AIR PORTUGAL reviews

Bad boarding, threat to force bag check mid journey, lines, late, buses, more waiting awful end to end.

Check in was excellent thanks to the team at the check in counter. I was disappointed to see that one has to pay for coffee on the flight. This is the first time I have seen that after 60 years of flying.

Our steward Margarida who served us from Lisbon to Boston was absolutely fantastic! She deserves a raise. Conscientious and thorough as well as showing appropriate attention for every need.

An old airplane with very uncomfortable seats in the Comfort “class! Small, narrow, and hard seat. Entertainment options are inferior, old movies. Boarding started at the back of the airplane, as we entered the aircraft last instead of after business class, risking the possibility that the comfort section would not have room for carry-on in the overhead bin. The food was ok. White wine was terrible. Overall, the flight felt worse than cheap airliners, and the price was as high as premium carriers.

I will avoid TAP if I can, the ground experience was very poor with bad behaviour from the ground crew and it was only a bit better on the aircraft.

I had a business class ticket from EWR to Madrid with a layover at LIS for 11 hours. It was obvious that I needed to pick up my luggage in Lisbon for 11 hours and check it in again when boarding the second flight to Madrid. Before buying the ticket, I called TAP customer service. Customer service assured me that I could get my luggage in Lisbon. When I arrived at Newark airport, I immediately asked to check my luggage to Lisbon. However, the TAP employee refused me, saying that I should resolve this issue upon arrival in Lisbon. She checked my luggage to Madrid. I asked the TAP employee at the gate to help me when boarding the plane, I asked the flight attendants manager on board the plane to help me. All the employees refused to help me and said that I should resolve this issue in Lisbon. It took me 4 hours to resolve this issue in Lisbon. I arrived at 11am and they didn't give me my luggage until 3pm. As a result, I was so tired after a sleepless night on the plane and 4 hours on my feet at the airport and all my plans were ruined that I couldn't fly to Madrid. It was a terrible experiance,

The seats were not designed to comfortably see people in coach for more than 10 minutes

A good, comfortable flight with friendly crew and good entertainment options.

Very rude person at the boarding desk; flight attendant coughing 3 inches from my face three times- not even covering her mouth; boarding process very unacceptable for older people with stairs to all planes (are you all stuck in the 1960’s?). I am sure that I am not remembering all of the negative things, but I am sure you get the message!

There was chaos at the Naples airport. We arrived three hours early for the flight but there was no invitation available about where to go to check bags until an hour later. Then we had to go to a different terminal to check our bags and check in and back to the first to board.

Everything you need to know for your flight from Chicago to Madeira

Information on your arrival and departure airports

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