$255 Find Cheap Flights from Chicago to Madeira - Compare and Save

1 adult
1 adult, Economy, 0 bags

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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 typical for this route right now.

Flights to Madeira from Chicago O'Hare Intl Airport usually cost between $576 and $1,875 in December.
The lowest price found in the past 5 days was $735 on TAP AIR PORTUGAL (Dec 6-Dec 17).

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 January, when tickets cost $542 (return) on average. On the other hand, the most expensive months are June and August, when the average cost of round-trip tickets is $1,432 and $1,289 respectively.

Good to know

Low season

January

Cheapest flight

$255
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 18% 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

 
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
6.4Entertainment
7.1Boarding
7.8Crew
6.3Food
Airline reviews

Business class seats were harder than expected, and lie flat we're not very comfortable. Less expensive than other business class flights, and much better than flying economy. The crew was excellent, as was the food.

10.0 ExcellentBarbara, Oct 2026
Read more TAP AIR PORTUGAL reviews

Business class seats were harder than expected, and lie flat we're not very comfortable. Less expensive than other business class flights, and much better than flying economy. The crew was excellent, as was the food.

Boarding was slow and getting off the plane took a long time. The crew did not have enough water for the trip.

Boarding was a bit chaotic, planes were on the oldish side. Otherwise, very nice flight. Would fly them again.

Turkey slices for breakfast. What happened to eggs, bacon, and sausage? The TV shows could’ve been more comprehensive as well as the movies.

The in flight meal was absolutely delicious. One thing I noted was that the meals weren’t just prepackaged tv dinner style options but were actual prepared meals you could tell were cooked that day in a kitchen and individually packaged for the flight.

On time. Good meal. Overhead cabin lights inop in entire cabin. Seat recliner did not work.

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.

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