$817 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 10/5. 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

Mon, Oct 5 - Thu, Oct 15
Multiple Airlines Logo
6:35 pm - 12:55 pm
ORD
-
FNC
36h 20m
2 stops
Multiple Airlines Logo
1:05 pm - 9:05 am
FNC
-
ORD
26h 00m
2 stops
$817Multiple Airlines
Fri, Oct 9 - Sun, Oct 11
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pm
ORD
-
FNC
18h 35m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:00 pm
FNC
-
ORD
17h 55m
1 stop
$818TAP AIR PORTUGAL
Thu, Oct 15 - Tue, Oct 27
Scandinavian Airlines Logo
6:00 am - 10:00 am
ORD
-
FNC
46h 00m
2 stops
Scandinavian Airlines Logo
3:00 pm - 9:33 pm
FNC
-
ORD
35h 33m
2 stops
$822Scandinavian Airlines
Thu, Oct 15 - Tue, Oct 27
Scandinavian Airlines Logo
6:00 am - 10:00 am
ORD
-
FNC
46h 00m
2 stops
Scandinavian Airlines Logo
3:00 pm - 9:33 pm
FNC
-
ORD
35h 33m
2 stops
$823Scandinavian Airlines
Sat, Oct 10 - Sat, Oct 17
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
$826TAP AIR PORTUGAL
Thu, Sep 17 - Tue, Sep 22
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 am
ORD
-
FNC
11h 40m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$828TAP AIR PORTUGAL
Tue, Oct 13 - Sun, Oct 18
Multiple Airlines Logo
6:35 pm - 12:25 pm
ORD
-
FNC
35h 50m
2 stops
Multiple Airlines Logo
11:20 am - 9:05 am
FNC
-
ORD
27h 45m
2 stops
$838Multiple Airlines
Sat, Oct 10 - Sat, Oct 17
TAP AIR PORTUGAL Logo
6:05 pm - 11:40 am
ORD
-
FNC
11h 35m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:05 pm
FNC
-
ORD
18h 00m
1 stop
$852TAP AIR PORTUGAL
Thu, Sep 24 - Tue, Sep 29
TAP AIR PORTUGAL Logo
6:00 pm - 11:40 am
ORD
-
FNC
11h 40m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$861TAP AIR PORTUGAL
Thu, Sep 24 - Tue, Sep 29
TAP AIR PORTUGAL Logo
6:00 pm - 1:15 pm
ORD
-
FNC
13h 15m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$871TAP 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 October.

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 seasonFebruary
Cheapest flight$817
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 15% 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 2223 reviews
7.0Boarding
6.2Food
7.1Comfort
7.8Crew
6.3Entertainment
Airline reviews

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.

4.0 OkayTuula, Apr 2026
SFO - LIS
Read more TAP AIR PORTUGAL reviews

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.

They left our luggage uncovered on tarmac in pouring rain during an hour delay of departure! At our final destination, we found ALL OF OUR CLOTHES/SHOES soaked all the way through!! Our 1st connection plane was a great business class accommodation but only 50 minutes long. Our 2nd connection from Lisbon (another delay with luggage uncovered on tarmac) had only the extra legroom and mediocre food in business class - no entertainment and no extra comfort seating. Will not use TAP Air Portugal again!

The food left a lot to be desired. The crew was great

Horrible experience at tbe check in ladie she was very racist ,she doesn't speak portuguese too and forced me to check in my carrion bag and I saw everyone with carrion bag inside anda lot of space ,she was rude unprofessional

Departed late. Flight crew some of the most professional I have ever experienced. First time we’ve flown this airline

No difference between business class and normal same seat everything same, waste of money

They allowed me to book the flight, which took quite an effort to find the best option for us, and then 2 months later, cancelled it because they didn't think 90 minutes was enough time to get between connections. Why let me book the flight in the first place? I am somewhat disappointed in Kayak and will be choosing other options in the future

Absolutely unacceptable level of service for a Business class: lousy drink and food options, disgusting food (inedible meat, watery rice, etc...), pathetic level of attentiveness from staff, Business class restrooms were not accessible for long periods because blocked of by staff...overall extremely disappointing, will NEVER fly Business on TAP again.

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

Information on your arrival and departure airports