$257 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 3/2. 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

ons., apr. 8 - ons., apr. 15
KLM Logo
4:50 pm - 9:40 am
ORD
-
FNC
34h 50m
1 stop
KLM Logo
10:25 am - 2:15 pm
FNC
-
ORD
33h 50m
1 stop
$486KLM
tir., apr. 7 - tir., apr. 14
British Airways Logo
9:15 pm - 12:05 pm
ORD
-
FNC
32h 50m
1 stop
British Airways Logo
6:40 pm - 12:20 pm
FNC
-
ORD
23h 40m
1 stop
$487British Airways
man., feb. 23 - ons., mar. 4
British Airways Logo
6:08 am - 2:15 pm
ORD
-
FNC
26h 07m
2 stops
British Airways Logo
4:00 pm - 1:50 pm
FNC
-
ORD
27h 50m
1 stop
$489British Airways
ons., apr. 8 - ons., apr. 15
KLM Logo
7:00 pm - 9:40 am
ORD
-
FNC
32h 40m
2 stops
KLM Logo
10:25 am - 2:15 pm
FNC
-
ORD
33h 50m
1 stop
$491KLM
ons., mar. 11 - tir., mar. 17
British Airways Logo
11:40 am - 4:10 pm
ORD
-
FNC
23h 30m
2 stops
British Airways Logo
3:05 pm - 7:45 pm
FNC
-
ORD
33h 40m
1 stop
$492British Airways
man., feb. 23 - ons., mar. 4
KLM Logo
5:53 pm - 9:35 am
ORD
-
FNC
33h 42m
2 stops
KLM Logo
10:25 am - 5:43 pm
FNC
-
ORD
37h 18m
2 stops
$493KLM
man., feb. 23 - ons., mar. 4
British Airways Logo
11:38 am - 2:15 pm
ORD
-
FNC
20h 37m
2 stops
British Airways Logo
4:00 pm - 6:00 pm
FNC
-
ORD
32h 00m
2 stops
$494British Airways
lør., apr. 11 - man., apr. 20
British Airways Logo
8:36 pm - 6:10 pm
ORD
-
FNC
39h 34m
2 stops
British Airways Logo
7:00 pm - 12:20 pm
FNC
-
ORD
23h 20m
1 stop
$495British Airways
tir., mar. 10 - tor., mar. 19
British Airways Logo
9:35 pm - 11:10 am
ORD
-
FNC
32h 35m
1 stop
British Airways Logo
5:00 pm - 7:25 am
FNC
-
ORD
43h 25m
2 stops
$497British Airways
ons., apr. 8 - ons., apr. 15
KLM Logo
7:00 pm - 9:40 am
ORD
-
FNC
32h 40m
2 stops
KLM Logo
10:25 am - 11:57 pm
FNC
-
ORD
19h 32m
2 stops
$501KLM
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Madeira?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Madeira departing in April.

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 April, when tickets cost $576 (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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$257
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.

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 2121 reviews
7.8Crew
7.0Boarding
6.3Entertainment
6.2Food
7.1Comfort
Airline reviews

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.

4.0 OkayAnonymous, Jan 2026
BOS - LIS
Read more TAP AIR PORTUGAL reviews

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

Poor. Our flight was delayed and they told me I would be fine to make my connection in Lisbon, I missed it. Then they told me my bag would be automatically loaded onto my new flight to rome. It wasn’t. It’s been 4 days and I still don’t have it.

I like the price. I dislike the website where I wanted to ask questions about the unusual high prices of the luggage fees. I called the toll free number from the United States and I cannot get through. You should test your own toll free website for info and you will know what I am writing about.

Wonderful just hope the had more direct flights to Boston

Boarding process was fast and efficient. Short flight but on time and well organized. I would certainly fly TAP again.

Very borderline, low budget airline without low budget prices There are no counts of soda, everything is dispensed enlarged bottles and poured into tiny cups about 70 mL so in order to keep hydrated you have to take 3-4 cups at a time. Also, there was only one food item offered, pasta, they ran out of chicken right away. Snack was very poor. It was called tuna sandwich, which is truly borderline. The flight attend attendance seemed to be overworked and tired.

TAP‘s flight attendants seem to be among the least ambitious of all the international flight crews we’ve flown with. . When we left US and went to Portugal, and when we returned from Portugal, flight attendants were not very visible. Then did not offer frequent water breaks and when we had to go back to request water, I was almost an imposition. Meal quality was just average. The dinners were fine. Breakfast wraps were presented soggy.

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

Information on your arrival and departure airports