$377 Find Cheap Flights from Illinois to Madeira

1 adult
1 adult, Economy, 0 bags

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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$377
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago to Funchal

FAQs for booking flights from Illinois to Madeira

  • How does KAYAK find such low prices on flights from Illinois 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 Illinois to Madeira.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Madeira?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois 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 Illinois 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 Illinois 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 Illinois 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 Illinois to Madeira up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Madeira?

    There are 2 airports in Madeira. The busiest airport is Madeira Airport (FNC), with 96% of all flights arriving there.

  • What is the cheapest month to fly from Illinois to Madeira?

    The cheapest month for flights from Illinois 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 Illinois to Madeira?

    To get a below average price on the flight from Illinois 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.

  • How long is the flight to Madeira?

    An average nonstop flight from Illinois to Madeira takes 18h 30m, covering a distance of 3845 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Funchal (FNC) with an average flight time of 18h 30m.

  • What is the most popular destination in Madeira?

    Based on KAYAK flight searches, the most popular destination is Funchal (100% of total searches to Madeira).

Reviews of the top airline flying from Illinois to Madeira

 
Need help choosing which airline to fly with from Illinois 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
6.2Food
7.0Boarding
6.3Entertainment
7.8Crew
7.1Comfort
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 to Madeira

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Madeira
Business Class flights to Madeira
Premium Economy Class flights to Madeira
Economy Class flights to Madeira