$459 Find Cheap Flights from Chicago to Madeira

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Madeira departing on 11/7. 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

Cheap Flights from Chicago to Madeira

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Funchal
Funchal1 stop$459
Funchal
Funchal1 stop$459

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

Fri, Nov 7 - Sat, Nov 15
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
$459Scandinavian Airlines
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Fri, Oct 31 - Sat, Nov 8
Scandinavian Airlines Logo
8:20 pm - 3:20 pmORD-FNC
14h 00m1 stop
Scandinavian Airlines Logo
4:10 pm - 4:45 pmFNC-ORD
30h 35m1 stop
$469Scandinavian Airlines
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Tue, Nov 4 - Wed, Nov 12
Iberia Logo
4:45 pm - 1:30 pmORD-FNC
14h 45m1 stop
Iberia Logo
2:10 pm - 2:30 pmFNC-ORD
30h 20m1 stop
$514Iberia
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Tue, Nov 4 - Wed, Nov 12
Iberia Logo
4:45 pm - 1:30 pmORD-FNC
14h 45m1 stop
Iberia Logo
2:10 pm - 8:25 pmFNC-ORD
36h 15m2 stops
$524Iberia
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Wed, Nov 5 - Wed, Nov 12
Logo
5:10 pm - 4:10 pmORD-FNC
17h 00m1 stop
Logo
2:10 pm - 2:30 pmFNC-ORD
30h 20m1 stop
$536
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Wed, Nov 5 - Wed, Nov 12
Logo
11:48 am - 4:10 pmORD-FNC
22h 22m2 stops
Logo
2:10 pm - 2:30 pmFNC-ORD
30h 20m1 stop
$546
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Tue, Nov 4 - Mon, Nov 10
British Airways Logo
9:45 pm - 11:10 amORD-FNC
31h 25m1 stop
British Airways Logo
4:55 pm - 1:50 pmFNC-ORD
26h 55m1 stop
$551British Airways
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Wed, Nov 5 - Wed, Nov 12
British Airways Logo
4:06 pm - 4:10 pmORD-FNC
18h 04m2 stops
British Airways Logo
3:55 pm - 5:38 pmFNC-ORD
31h 43m2 stops
$565British Airways
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Wed, Nov 5 - Tue, Nov 11
TAP AIR PORTUGAL Logo
7:10 pm - 10:55 pmORD-FNC
21h 45m1 stop
TAP AIR PORTUGAL Logo
6:15 pm - 3:00 pmFNC-ORD
26h 45m1 stop
$591TAP AIR PORTUGAL
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Fri, Dec 5 - Thu, Dec 11
TAP AIR PORTUGAL Logo
8:15 pm - 1:30 pmORD-FNC
11h 15m1 stop
TAP AIR PORTUGAL Logo
4:10 am - 3:15 pmFNC-ORD
17h 05m1 stop
$611TAP AIR PORTUGAL
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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 $576 (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 seasonJanuary
Cheapest flight$459
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 8% 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 1951 reviews
6.3Entertainment
6.2Food
7.8Crew
7.0Boarding
7.1Comfort
Airline reviews

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

4.0 OkayAnonymous, Aug 2025IAD - LIS
Read more TAP AIR PORTUGAL reviews

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.

We flew TAP last October from Newark to Lisbon. The meal was bad. This flight had good food. Also, this flight was delayed. There were TAP employees waiting at Lisbon to make sure we made our connecting flight. I find the TAP website and app frustrating, but the service once we reached the airport was very good

The airport temperature at the airport and on the flight was too warm

Boarding too way too long. Biggest peeve: zero in-seat power in economy! No plug sockets, no USB ports. Plane was an A330, so not old.

boarding is so disorganized, i was literally appalled at the boarding experience

Comfortable but not Polaris or Delta comfort Business Class. Overall 7 out of 10

Tap air Portugal was the best I will traveling again with u guys. Thank u.

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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