$756 Find Cheap Flights from Chicago to Madeira - Compare and Save

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 11/1. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Sun, Nov 1 - Sat, Nov 14
TAP AIR PORTUGAL Logo
8:10 pm - 10:55 pm
ORD
-
FNC
20h 45m
1 stop
TAP AIR PORTUGAL Logo
4:10 am - 3:30 pm
FNC
-
ORD
17h 20m
1 stop
$756TAP AIR PORTUGAL
Thu, Oct 8 - Sun, Oct 11
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 am
ORD
-
FNC
11h 40m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:00 pm
FNC
-
ORD
17h 55m
1 stop
$835TAP AIR PORTUGAL
Sat, Oct 10 - Sat, Oct 17
TAP AIR PORTUGAL Logo
6:05 pm - 9:05 pm
ORD
-
FNC
21h 00m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$836TAP AIR PORTUGAL
Fri, Oct 2 - Tue, Oct 6
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pm
ORD
-
FNC
18h 35m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$844TAP AIR PORTUGAL
Fri, Oct 2 - Tue, Oct 6
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 am
ORD
-
FNC
11h 40m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$845TAP AIR PORTUGAL
Thu, Jul 9 - Thu, Jul 16
TAP AIR PORTUGAL Logo
4:45 pm - 8:20 am
ORD
-
FNC
33h 35m
1 stop
TAP AIR PORTUGAL Logo
10:00 pm - 4:00 pm
FNC
-
ORD
24h 00m
1 stop
$849TAP AIR PORTUGAL
Wed, Sep 30 - Wed, Oct 7
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 am
ORD
-
FNC
11h 40m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 4:00 pm
FNC
-
ORD
16h 10m
1 stop
$854TAP AIR PORTUGAL
Wed, Sep 30 - Thu, Oct 8
TAP AIR PORTUGAL Logo
6:00 pm - 3:35 pm
ORD
-
FNC
15h 35m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 12:40 pm
FNC
-
ORD
12h 50m
1 stop
$855TAP AIR PORTUGAL
Sun, Sep 27 - Wed, Oct 7
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pm
ORD
-
FNC
18h 35m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 12:40 pm
FNC
-
ORD
20h 45m
1 stop
$860TAP AIR PORTUGAL
Sat, Oct 3 - Sat, Oct 10
TAP AIR PORTUGAL Logo
6:05 pm - 11:40 am
ORD
-
FNC
11h 35m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$866TAP AIR PORTUGAL
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 November.

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 $462 (return) on average. On the other hand, the most expensive months are June and August, when the average cost of round-trip tickets is $840 and $704 respectively.

Good to know

Low seasonSeptember
Cheapest flight$756
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 10% 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.
7.2
TAP AIR PORTUGALOverall score based on 2274 reviews
7.1Comfort
7.0Boarding
6.2Food
7.8Crew
6.3Entertainment
Airline reviews

The crew was excellent. What I did not enjoy was the food. I have taken many international flights and this was on the low end. Otherwise the trip was fine.

8.0 ExcellentAnonymous, Jun 2026
BOS - LIS
Read more TAP AIR PORTUGAL reviews

The crew was excellent. What I did not enjoy was the food. I have taken many international flights and this was on the low end. Otherwise the trip was fine.

Seats were the most uncomfortable seats i ever experienced on a flight to Europe from Boston. It was a waist of money in buying premium seats for top dollars. I want my money back for what i paid extra for my seats. Awful conditions!

On the seat map for this flight with TAP was shown a business class configuration of 2 rows/8 seats. To my surprise, 4 rows/24 seats being the middle is kept empty, old European type. I chose seat 2F, the the leg room economy dimension. This is not what I paid for. Disappointed!

Boarding felt a little chaotic as everyone was waiting around the gate. Food was great, service was good.

The passport control process in Lisbon ranks as a 1 on a 1 to 5 scale. Terrible. In line 2 hours and still missed our first flight. Next day, 1.5 hours but we made the flight. The Business Class food was poor. Unidentifiable. Not tasty at all. Unacceptable in BC. Attendants were adequate. Flight left late and arrived late. After this trip, we will not be flying TAP nor will we be connecting through Lisbon.

Flight attendants in business class were rather indifferent While in second leg operated by Portugalia TAP subsidiary were outstanfy

Great service overall. One of the best international flight experiences Ive had.

The chicken was so dry it was impossible to eat. No substitute was offered. The port to charge my phone was broken and all I got was a shrug from the crew. The entertainment system was glitchy and subtitles didn’t load. Crew seemed fully uninterested and unfriendly.

The flight crew were absolute rock stars. When they came to the gate they looked like royalty, so chic. They also were extremely kind. Food was good and I loved the lack of plastic waste. The flight was lovely and smooth.

We were unable to check in due to technical problems on TAP’s end. The flight was delayed forty minutes with no reason given. We received timely notice of the flight delay. We were also notified of a gate change. The new gate was at a different terminal. When we got to the new terminal, we learned that we had to go back to the old terminal first to check in. This information should have been included along with the gate change notification. Also unexplained, the steward skipped us when offering breakfast.

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

Information on your arrival and departure airports