$340 Find Cheap Flights from Chicago to Madeira - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Chicago to Madeira

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Funchal
12h 30m2 stops
from $656per person
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?

Flight prices are below average for this route right now.

Flights to Madeira from Chicago O'Hare Intl Airport usually cost between $726 and $1,100 in February.
The lowest price found in the past 5 days was $656 on TAP AIR PORTUGAL (Feb 19-Feb 27).

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Madeira?

The cheapest month for flights from Chicago O'Hare Intl Airport to Madeira is April, when tickets cost $575 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,432 and $1,398 respectively.

Good to know

Low season

February

Cheapest flight

$340
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 22% lower on average.
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

 
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 2386 reviews
7.2Comfort
7.0Boarding
7.8Crew
6.4Entertainment
6.3Food
Airline reviews

The food was dry and tasteless. Boarding process was ridiculous. Lounge is Lisbon was of very poor quality. The website is nearly unusable. Customer service was challenging. This was my first transatlantic business class flight with TAP. There will not be another.

4.0 OkayAnonymous, Sep 2026
Read more TAP AIR PORTUGAL reviews

The food was dry and tasteless. Boarding process was ridiculous. Lounge is Lisbon was of very poor quality. The website is nearly unusable. Customer service was challenging. This was my first transatlantic business class flight with TAP. There will not be another.

Disappointing Compared to other airlines , this one was the most expensive. But not even close, in getting what you paid for.

TAP canceled connection and we had to wait 15 hours for another flight to Milan. There were plenty of. Seats on earlier but because we were Excellence Class the would not let us downgrade which we were willing to. Don’t understand their logic? Plenty of seats but we couldn’t / they wouldn’t make the change.

Excellent experience - from boarding through the super smooth flight The food was mediocre and the app could be better but overall great experience

This was one of the worst flights I have ever taken in my entire life. First of all, I traveled Economy, but the seats were TINY and cramped. Not just for me; everyone around me was complaining of the same thing and said they could not get comfortable. Then there was the issue of the heat. For whatever reason the heat on the plane must have been turned to FULL BLAST, because even at 30,000 feet, it was SWEALTERING. Everyone was drench in sweat. Then, they were SO STINGY with the amount of drink they would give you. If you asked for water, it was in a tiny, paper cup (think bathroom cup) and they only filled it 3/4s of the way as if the cost came right out of the pockets of the air stewards. Everything was a money grab, you could tell! You had to pay for the WiFi, which was garbage slow, and the onboard entertainment was limited and stale. If I EVER fly TAP again, it will not be Economy class. What a disaster!

They blocked me from checking in online and they charged me lots of money

Everything was good with Tap Air Portugal. It was Logan Airport that was a problem. The fuel system was down and delayed my 10:40 boarding. I wasn't able to board my flight until 2:00 am...after that my flights were great.

Did not enjoy the meal provided. The aircraft was dirty. For instance, the screen seemed to have been cleaned with a dirty rag. Disgusting.

Boarding went fast. Lisbon's gates are too small for the flights they serve.

Great pilot, textbook landing in madeira. Everything else, from booking to checkin, plane quality, seat amenities, crew engagement, and overall experience were significantly below standard. I WOULD NOT FLY TAP IF THERE IS ANY OTHER OPTION.

More options for your flight from Chicago to Madeira

Complete your trip to Madeira with a hotel stay or car rental