$371 Find Cheap Flights from Chicago to Madeira

This is the cheapest one-way 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

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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Flights Deals

Best Madeira Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Funchal
Funchal1 stop$585
Funchal
Funchal1 stop$585

Cheap Flight Deals from Chicago to Madeira (ORD-PTMA)

 
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.

Recent round-trip flight deals from Chicago to Madeira

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Madeira.
Discover the best prices for you by selecting your travel dates on KAYAK.
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pmORD-FNC
18h 35m1 stop
TAP AIR PORTUGAL Logo
9:50 pm - 4:10 pmFNC-ORD
24h 20m1 stop
$585TAP AIR PORTUGAL
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Sun, Oct 5 - Tue, Oct 14
TAP AIR PORTUGAL Logo
6:00 pm - 1:05 pmORD-FNC
13h 05m1 stop
TAP AIR PORTUGAL Logo
7:20 pm - 12:35 pmFNC-ORD
23h 15m1 stop
$601TAP AIR PORTUGAL
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Sun, Oct 5 - Wed, Oct 15
Iberia Logo
4:30 pm - 11:35 amORD-FNC
13h 05m1 stop
Iberia Logo
11:10 am - 7:45 pmFNC-ORD
38h 35m2 stops
$658Iberia
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Fri, Oct 24 - Sun, Nov 2
KLM Logo
4:20 pm - 9:20 amORD-FNC
35h 00m1 stop
KLM Logo
10:05 am - 2:10 pmFNC-ORD
34h 05m1 stop
$659KLM
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Tue, May 13 - Thu, May 22
Iberia Logo
10:08 am - 11:35 amORD-FNC
19h 27m2 stops
Iberia Logo
11:10 am - 7:45 pmFNC-ORD
38h 35m2 stops
$662Iberia
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Fri, Oct 24 - Sun, Nov 2
British Airways Logo
9:15 pm - 12:20 pmORD-FNC
33h 05m1 stop
British Airways Logo
12:50 pm - 2:55 pmFNC-ORD
31h 05m1 stop
$756British Airways
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Fri, Oct 17 - Sun, Oct 26
SWISS Logo
7:05 pm - 9:40 amORD-FNC
32h 35m1 stop
SWISS Logo
10:25 am - 3:55 pmFNC-ORD
35h 30m1 stop
$820SWISS
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Wed, May 14 - Wed, May 21
SWISS Logo
7:05 pm - 9:35 amORD-FNC
32h 30m1 stop
SWISS Logo
10:25 am - 12:10 pmFNC-ORD
31h 45m1 stop
$839SWISS
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Mon, Oct 6 - Wed, Oct 15
KLM Logo
4:20 pm - 9:20 amORD-FNC
35h 00m1 stop
KLM Logo
10:05 am - 2:10 pmFNC-ORD
34h 05m1 stop
$845KLM
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Tue, May 20 - Thu, May 29
British Airways Logo
8:30 pm - 12:20 pmORD-FNC
33h 50m2 stops
British Airways Logo
12:50 pm - 2:55 pmFNC-ORD
31h 05m1 stop
$868British Airways
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Fri, Oct 17 - Sun, Oct 26
Useful Info

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.

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 January, when tickets cost $632 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $1,354 and $1,159 respectively.

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Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$371
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 1% 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.

  • What is the cheapest time of day to fly to Madeira?

    The cheapest time of day to fly to Madeira is generally at night, when round-trip flights cost $786 on average. Morning departures are around 12% cheaper than evening flights, on average. The most expensive time of day to fly to Madeira is generally in the evening, which is peak travel time and where the average cost of a ticket is $1,073.

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 1851 reviews
7.0Boarding
6.3Entertainment
7.8Crew
7.1Comfort
6.2Food
Airline reviews

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

2.0 MediocreSuzanne, Mar 2025SVQ - LIS
Read more TAP AIR PORTUGAL reviews

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

Little leg room in business. I am tall and could use more.

Was a cheap flight and it got me to Portugal on time. For economy there was ample leg room and the flight attendants were pleasant and helpful.

Flight was packed. This was a very uncomfortable experience. Boarding process could be explained better. Despite recommending a window seat when travelling with a pet in the cabin, the seat in front of me had less space than the center and aisle seats. For Premium Economy, the seats were crammed with minimal legroom. I hate to think what Regular Economy was like. The cabin crew missed me at first when handing out meals. When my meal eventually came, there were no utensils. I'd originally booked to fly Business Class; those seats didn't look that great either.

Flight was packed. This was a very uncomfortable experience. Boarding process could be explained better. Despite recommending a window seat when travelling with a pet in the cabin, the seat in front of me had less space than the center and aisle seats. For Premium Economy, the seats were crammed with minimal legroom. I hate to think what Regular Economy was like. The cabin crew missed me at first when handing out meals. When my meal eventually came, there were no utensils.

First time and I enjoyed the trip…. Will fly again soon 🔜

Delayed flight because other plane was occupying the gate for longer than expected. Once we boarded the plane had to wait 1 hour before taking off. We. Almost lost our connection flight and the baggage didn’t make it. We had to wait two days to receive our luggage. Hope they improve the timing or work with the airport to get better service.

I’m still missing my bags. I’m soo frustrated

TAP boarding gate agents singled out Group A line to gate check all carry on bags …. Supposedly because of lack on bin space. BUT ALL OTHERS WERE PERMITTED WITH CARRY ON BAGS. Additionally so many passengers entering the plane after us were permitted carry on bags. And when the plane was fully loaded, there was a number of open spaces in the overhead bins. I WILL SEARCH OTHER OPTIONS BEFORE FLYING TAP AGAIN

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

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

Information on your arrival and departure airports

Chicago (ORD)

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