$286 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 7/31. 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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Flights Deals

Best Madeira Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Funchal
Funchal1 stop$529
Funchal
Funchal1 stop$529

Cheap Flights from Chicago to Madeira

 
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, Sep 11 - Wed, Sep 17
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 amORD-FNC
11h 40m1 stop
TAP AIR PORTUGAL Logo
12:40 pm - 10:55 amFNC-ORD
28h 15m1 stop
$529TAP AIR PORTUGAL
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Thu, Nov 27 - Sat, Dec 6
Scandinavian Airlines Logo
7:20 pm - 1:45 pmORD-FNC
36h 25m2 stops
Scandinavian Airlines Logo
4:10 pm - 4:45 pmFNC-ORD
30h 35m1 stop
$540Scandinavian Airlines
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Sun, Aug 24 - Thu, Sep 4
Iberia Logo
5:40 pm - 3:05 pmORD-FNC
39h 25m2 stops
Iberia Logo
1:05 pm - 2:15 pmFNC-ORD
31h 10m1 stop
$669Iberia
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Mon, Aug 25 - Thu, Sep 4
Iberia Logo
4:30 pm - 3:05 pmORD-FNC
16h 35m2 stops
Iberia Logo
1:05 pm - 2:15 pmFNC-ORD
31h 10m1 stop
$671Iberia
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Sun, Aug 24 - Tue, Sep 2
British Airways Logo
9:15 pm - 6:10 pmORD-FNC
14h 55m1 stop
British Airways Logo
6:40 pm - 3:55 pmFNC-ORD
27h 15m1 stop
$701British Airways
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Sat, Aug 23 - Tue, Sep 2
British Airways Logo
8:26 pm - 6:10 pmORD-FNC
39h 44m2 stops
British Airways Logo
6:40 pm - 3:55 pmFNC-ORD
27h 15m1 stop
$706British Airways
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Mon, Aug 25 - Mon, Sep 1
KLM Logo
4:20 pm - 9:35 amORD-FNC
35h 15m1 stop
KLM Logo
10:15 am - 2:10 pmFNC-ORD
33h 55m1 stop
$713KLM
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Tue, Jul 15 - Wed, Jul 23
KLM Logo
4:20 pm - 9:20 amORD-FNC
35h 00m1 stop
KLM Logo
10:20 am - 2:10 pmFNC-ORD
33h 50m1 stop
$722KLM
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Fri, Oct 3 - Mon, Oct 13
Logo
4:00 pm - 8:35 amORD-FNC
34h 35m3 stops
Logo
2:15 pm - 5:33 pmFNC-ORD
33h 18m3 stops
$756
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Thu, Sep 11 - Wed, Sep 17
Logo
6:00 pm - 7:25 pmORD-FNC
19h 25m1 stop
Logo
9:40 am - 10:55 amFNC-ORD
31h 15m2 stops
$770
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Useful Info

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 $613 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,378 and $1,153 respectively.

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Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$286
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% 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 1893 reviews
6.3Entertainment
7.8Crew
7.0Boarding
6.2Food
7.1Comfort
Airline reviews

Food was edible, not great, and served by attendants who looked like they really were not happy working the flight. The section I was in was too warm making the 11 hour flight uncomfortable. Other areas on the plane were fine.

8.0 ExcellentMarc, Jun 2025LAX - LIS
Read more TAP AIR PORTUGAL reviews

Food was edible, not great, and served by attendants who looked like they really were not happy working the flight. The section I was in was too warm making the 11 hour flight uncomfortable. Other areas on the plane were fine.

I’ve never had worse food in business class ever!

Checked bG chstgr was extremely high. Over $120. It was s bsit and switch knowing an international passenger would have t9 check a bag.

First, communication was terrible. The gate on our ticket was not what was reflected on the airport screens and TAP personnel were not present at either gate to answer questions. The flight was delayed and there was no announcement. Also, there was an equipment swap to a smaller airframe which affected our level of comfort. The root of all these issues was as a lack of communication. With air travel in foreign countries already being a stressful affair, lack of communication needlessly raises the level of difficulty.

Checkin was very slow, we had checked in online and hoping we could do a bag drop at the airport. However everyone with checked bags had to queue up and it took over 40mins. Our advice arrive extra early or you will be rushing to the gate.

On time, politeness, food okay but entertneiment mediocre with only old movie and the so called new we’re 2 or 3…

Do you have a bad service And And treat customers terrible

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

Little leg room in business. I am tall and could use more.

Was a cheap flight and it got me to Portugal on time. For economy there was ample leg room and the flight attendants were pleasant and helpful.

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

Information on your arrival and departure airports

Chicago (ORD)

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