$376 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 3/15. 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, 0 bags

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

Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
4:55 pm - 12:25 pm
ORD
-
FNC
13h 30m
1 stop
Multiple Airlines Logo
1:35 pm - 9:02 am
FNC
-
ORD
25h 27m
2 stops
$525Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
4:55 pm - 12:25 pm
ORD
-
FNC
13h 30m
1 stop
Multiple Airlines Logo
1:35 pm - 2:25 pm
FNC
-
ORD
30h 50m
1 stop
$526Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
8:01 am - 12:25 pm
ORD
-
FNC
22h 24m
2 stops
Multiple Airlines Logo
1:35 pm - 8:25 am
FNC
-
ORD
24h 50m
2 stops
$529Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Iberia Logo
4:55 pm - 12:25 pm
ORD
-
FNC
13h 30m
1 stop
Iberia Logo
1:35 pm - 9:38 pm
FNC
-
ORD
38h 03m
2 stops
$536Iberia
Mon, Apr 20 - Mon, May 4
Iberia Logo
7:05 pm - 12:55 pm
ORD
-
FNC
35h 50m
2 stops
Iberia Logo
1:20 pm - 2:25 pm
FNC
-
ORD
31h 05m
1 stop
$539Iberia
Sat, Apr 25 - Thu, May 7
Iberia Logo
7:00 pm - 12:40 pm
ORD
-
FNC
35h 40m
2 stops
Iberia Logo
1:05 pm - 2:25 pm
FNC
-
ORD
31h 20m
1 stop
$542Iberia
Sun, Apr 26 - Thu, May 7
Multiple Airlines Logo
7:25 pm - 1:15 am
ORD
-
FNC
23h 50m
2 stops
Multiple Airlines Logo
6:05 am - 6:15 pm
FNC
-
ORD
18h 10m
2 stops
$551Multiple Airlines
Sat, Apr 25 - Thu, May 7
Iberia Logo
10:30 pm - 12:40 pm
ORD
-
FNC
32h 10m
1 stop
Iberia Logo
1:05 pm - 2:25 pm
FNC
-
ORD
31h 20m
1 stop
$560Iberia
Mon, Apr 13 - Mon, Apr 20
British Airways Logo
7:05 pm - 6:35 pm
ORD
-
FNC
17h 30m
1 stop
British Airways Logo
6:55 pm - 1:50 pm
FNC
-
ORD
24h 55m
1 stop
$562British Airways
Mon, Apr 13 - Mon, Apr 20
British Airways Logo
3:16 pm - 6:35 pm
ORD
-
FNC
21h 19m
2 stops
British Airways Logo
6:55 pm - 1:50 pm
FNC
-
ORD
24h 55m
1 stop
$566British Airways
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 February, when tickets cost $535 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,494 and $1,378 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Madeira?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Madeira, you should book around 5 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$376
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 12% 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.

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 2155 reviews
7.8Crew
7.1Comfort
6.2Food
6.3Entertainment
7.0Boarding
Airline reviews

The plane was small and one felt the turbulence much more. The lines to get through immigration were insanely long.

4.0 OkayAnonymous, Feb 2026
DUS - LIS
Read more TAP AIR PORTUGAL reviews

The plane was small and one felt the turbulence much more. The lines to get through immigration were insanely long.

First time flying Business with Tap, I think it was a very good experience. It beats many domestic US carriers, the food options were really great, authentic Portuguese food, wines & deserts. Next time will do the free 24-48 hour stopover in Lisbon or Porto for sure.

We upgraded to business class. Nice seat with lots of room but otherwise not impressive.

Delayed departure Madrid to Lisboa and my luggage no arrived

this flight was awful from pre-boarding to on the plane. There needs to be more coordination between TAP and My Way. We were in first class and I am handicapped. BY the time we got on the plane there was no place for our baggage and the crew did not handle the situation well. They gave us an argument and said that we'd have to have it checked. Then, after I complained they moved some people's bags to put our small carry ons several seats back of our seats which were in Row 4.

Late. Lack of updates. Rude hostesses. Terrible food. Lack of headphones.

Flight was delayed but crew gave little to no communication, then “began boarding” but really just had everyone stand up and wait for an hour without any news or updates, as if we were going to start boarding at any second. Total chaos. Seemed like this was their first time boarding a plane. When we arrived at our destination, we waited for over an hour for the baggage claim belt to even turn on. Probably waited at baggage claim for our luggage for close to two hours. Everyone was very confused and of course we all worried that the luggage was lost. Again, zero communication and everyone we asked just said “I don’t know.” So we were left wondering whether to wait, or file a missing baggage claim, or check the other baggage claim belts (which we did every fifteen-twenty minutes because we were just confused). Lack of communication throughout the experience was a huge issue.

The value is there, but the layovers in Lisbon were not great. The passport control was so bad that a 2 hour layover became very tight and on the return the Terminal was barebones which made it a long 3 hours.

From Casablanca to Lisbon our baggage 2 pound over they want me to pay $120 for 2 pound which unexpected we are two family 8 of us they counters lady her customer service is not good I fly frequently for my business next time fly with TAP Air I will think twice

Booked business with TAP from LAX to Cabo Verde - overall ok, but just doesn’t feel like business class. More of a budget airline

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

Information on your arrival and departure airports