When did momondo last update prices for flights from Chicago to Madeira?

Prices for flights from Chicago to Madeira are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Madeira?

There is 1 operator available for flights from Chicago to Madeira as of October 2026.

How old do you have to be to fly from Chicago to Madeira?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Madeira.

What documentation or ID do you need to fly to Madeira?

The required travel and health documents for your Madeira trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madeira. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$255 Cheap Flights from Chicago to Madeira in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Madeira

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:10 pm - 1:45 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

36h 35m2 stops Kastrup Copenhagen Stockholm Arlanda

4:25 pm - 4:45 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

30h 20m1 stop Kastrup Copenhagen

$718Scandinavian Airlines

Thu, Jan 21 - Sat, Jan 30

7:10 pm - 1:45 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

36h 35m2 stops Kastrup Copenhagen Stockholm Arlanda

2:35 pm - 4:45 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

32h 10m2 stops Stockholm Arlanda Kastrup Copenhagen

$724Scandinavian Airlines

Thu, Jan 21 - Sat, Jan 30

8:10 pm - 5:10 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

15h 00m1 stop Lisbon Humberto Delgado

9:55 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

23h 35m1 stop Lisbon Humberto Delgado

$735TAP AIR PORTUGAL

Sun, Dec 6 - Thu, Dec 17

8:10 pm - 8:15 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

18h 05m1 stop Lisbon Humberto Delgado

7:50 am - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

13h 40m1 stop Lisbon Humberto Delgado

$743TAP AIR PORTUGAL

Sun, Feb 28 - Sun, Mar 7

8:10 pm - 10:55 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

20h 45m1 stop Lisbon Humberto Delgado

7:50 am - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

13h 40m1 stop Lisbon Humberto Delgado

$744TAP AIR PORTUGAL

Sun, Dec 6 - Sun, Dec 13

7:35 pm - 9:15 amORD Chicago O'Hare Intl-FNC Funchal Madeira

31h 40m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol

6:15 pm - 4:37 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

28h 22m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County

$751KLM

Tue, Apr 20 - Tue, Apr 27

5:45 pm - 1:30 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

13h 45m1 stop Lisbon Humberto Delgado

7:35 pm - 4:00 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

26h 25m1 stop Lisbon Humberto Delgado

$753TAP AIR PORTUGAL

Sun, Apr 18 - Tue, Apr 27

5:45 pm - 6:35 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

18h 50m1 stop Lisbon Humberto Delgado

4:05 am - 4:00 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

17h 55m1 stop Lisbon Humberto Delgado

$762TAP AIR PORTUGAL

Fri, Apr 9 - Sun, Apr 18

7:10 pm - 1:45 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

36h 35m2 stops Kastrup Copenhagen Stockholm Arlanda

4:25 pm - 4:45 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

30h 20m1 stop Kastrup Copenhagen

$764Scandinavian Airlines

Thu, Jan 21 - Sat, Jan 30

7:35 pm - 5:25 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

39h 50m2 stops Detroit Metropolitan Wayne County Amsterdam Schiphol

6:15 pm - 4:37 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

28h 22m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County

$766KLM

Sun, Apr 18 - Tue, Apr 27

Cheap last minute flights

Enter your travel dates to find the best prices.

8:10 pm - 10:20 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

20h 10m1 stop Lisbon Humberto Delgado

6:10 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

27h 20m1 stop Lisbon Humberto Delgado

$692TAP AIR PORTUGAL

Sun, Nov 1 - Tue, Nov 10

8:10 pm - 10:55 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

20h 45m1 stop Lisbon Humberto Delgado

6:10 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

27h 20m1 stop Lisbon Humberto Delgado

$725TAP AIR PORTUGAL

Sun, Nov 1 - Tue, Nov 10

1:00 pm - 10:20 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

27h 20m2 stops Boston Logan Intl Lisbon Humberto Delgado

6:10 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

27h 20m1 stop Lisbon Humberto Delgado

$866TAP AIR PORTUGAL

Sun, Nov 1 - Tue, Nov 10

8:10 pm - 10:20 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

20h 10m1 stop Lisbon Humberto Delgado

12:40 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

32h 50m2 stops Milan Malpensa Lisbon Humberto Delgado

$881Multiple Airlines

Sun, Nov 1 - Tue, Nov 10

8:10 pm - 8:35 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

18h 25m2 stops Lisbon Humberto Delgado Porto

9:10 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

24h 20m2 stops Porto Lisbon Humberto Delgado

$892Multiple Airlines

Sun, Nov 1 - Tue, Nov 10

8:10 pm - 9:15 amORD Chicago O'Hare Intl-FNC Funchal Madeira

31h 05m1 stop Lisbon Humberto Delgado

2:10 pm - 3:30 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

31h 20m3 stops Porto London Gatwick Lisbon Humberto Delgado

$1,028TAP AIR PORTUGAL

Sun, Nov 1 - Tue, Nov 10

6:25 pm - 10:55 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

22h 30m3 stops Paris Charles de Gaulle Lyon-Saint Exupéry Lisbon Humberto Delgado

3:55 pm - 5:20 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

31h 25m3 stops Stockholm Arlanda Kastrup Copenhagen Reykjavik Keflavik Intl

$1,129Multiple Airlines

Sun, Nov 1 - Tue, Nov 10

8:10 pm - 11:10 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

21h 00m2 stops Lisbon Humberto Delgado Porto

4:10 am - 5:20 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

19h 10m3 stops Lisbon Humberto Delgado Brussels Bruxelles-National Reykjavik Keflavik Intl

$1,164Multiple Airlines

Sun, Nov 1 - Mon, Nov 9

8:10 pm - 8:35 pmORD Chicago O'Hare Intl-FNC Funchal Madeira

18h 25m2 stops Lisbon Humberto Delgado Porto

3:55 pm - 5:20 pmFNC Funchal Madeira-ORD Chicago O'Hare Intl

31h 25m3 stops Stockholm Arlanda Kastrup Copenhagen Reykjavik Keflavik Intl

$1,204Multiple Airlines

Sun, Nov 1 - Tue, Nov 10

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TAP AIR PORTUGAL flights from Chicago to Madeira

Our best TAP AIR PORTUGAL deals on Chicago to Madeira flight tickets

TAP AIR PORTUGAL

Nov 1

ORD8:10 pmChicago O'Hare Intl

20h 10m

1 stop

FNC10:20 pmFunchal Madeira

Nov 10

FNC6:10 pmFunchal Madeira

27h 20m

1 stop

ORD3:30 pmChicago O'Hare Intl

$692

TAP AIR PORTUGAL

Nov 1

ORD8:10 pmChicago O'Hare Intl

20h 45m

1 stop

FNC10:55 pmFunchal Madeira

Nov 10

FNC6:10 pmFunchal Madeira

27h 20m

1 stop

ORD3:30 pmChicago O'Hare Intl

$725

TAP AIR PORTUGAL

Dec 6

ORD8:10 pmChicago O'Hare Intl

15h 00m

1 stop

FNC5:10 pmFunchal Madeira

Dec 17

FNC9:55 pmFunchal Madeira

23h 35m

1 stop

ORD3:30 pmChicago O'Hare Intl

$735

KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets

KLM

Apr 20

ORD7:35 pmChicago O'Hare Intl

31h 40m

2 stops

FNC9:15 amFunchal Madeira

Apr 27

FNC6:15 pmFunchal Madeira

28h 22m

2 stops

ORD4:37 pmChicago O'Hare Intl

$751

KLM

Apr 18

ORD7:35 pmChicago O'Hare Intl

39h 50m

2 stops

FNC5:25 pmFunchal Madeira

Apr 27

FNC6:15 pmFunchal Madeira

28h 22m

2 stops

ORD4:37 pmChicago O'Hare Intl

$766

KLM

Apr 20

ORD7:35 pmChicago O'Hare Intl

31h 40m

2 stops

FNC9:15 amFunchal Madeira

Apr 27

FNC6:15 pmFunchal Madeira

26h 00m

1 stop

ORD2:15 pmChicago O'Hare Intl

$782

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Thu 1/21

7:10 pm-1:45 pm

2 stops36h 35m

Funchal Madeira

Sat 1/30

4:25 pm-4:45 pm

1 stop30h 20m

$718

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Thu 1/21

7:10 pm-1:45 pm

2 stops36h 35m

Funchal Madeira

Sat 1/30

2:35 pm-4:45 pm

2 stops32h 10m

$724

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Sun 12/6

8:10 pm-5:10 pm

1 stop15h 00m

Funchal Madeira

Thu 12/17

9:55 pm-3:30 pm

1 stop23h 35m

$735

Quickest round-trip

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Sun 2/28

8:10 pm-8:15 pm

1 stop18h 05m

Funchal Madeira

Sun 3/7

7:50 am-3:30 pm

1 stop13h 40m

$743

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Sun 12/6

8:10 pm-10:55 pm

1 stop20h 45m

Funchal Madeira

Sun 12/13

7:50 am-3:30 pm

1 stop13h 40m

$744

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Tue 4/20

7:35 pm-9:15 am

2 stops31h 40m

Funchal Madeira

Tue 4/27

6:15 pm-4:37 pm

2 stops28h 22m

$751

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Sun 4/18

5:45 pm-1:30 pm

1 stop13h 45m

Funchal Madeira

Tue 4/27

7:35 pm-4:00 pm

1 stop26h 25m

$753

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Fri 4/9

5:45 pm-6:35 pm

1 stop18h 50m

Funchal Madeira

Sun 4/18

4:05 am-4:00 pm

1 stop17h 55m

$762

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Thu 1/21

7:10 pm-1:45 pm

2 stops36h 35m

Funchal Madeira

Sat 1/30

4:25 pm-4:45 pm

1 stop30h 20m

$764

ChicagoFunchal

ORD Chicago O'Hare Intl - FNC Funchal Madeira

ORDFNC

Chicago O'Hare Intl

Sun 4/18

7:35 pm-5:25 pm

2 stops39h 50m

Funchal Madeira

Tue 4/27

6:15 pm-4:37 pm

2 stops28h 22m

$766

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Madeira

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Madeira?

The cheapest month to fly to Madeira from Chicago is in January. Flight prices, which tend to average around $542, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Madeira from Chicago during April instead. Flights to Madeira in April, while not as cheap as those in January, still average around $575.

Cheap Chicago to Madeira flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Madeira

Best Price Found	$255
Fastest flight time	11h 50m
Direct flights	None

The best one-way flight to Madeira from Chicago in the past 72 hours is $255. The best round-trip flight deal from Chicago to Madeira found on momondo in the last 72 hours is $718.

The fastest flight from Chicago to Madeira takes 11h 50m

There are no direct flights from Chicago to Madeira. There are no popular flight routes from Chicago to Madeira.

Search flight deals

Frequently asked questions about flying from Chicago to Madeira

When did momondo last update prices for flights from Chicago to Madeira?
Prices for flights from Chicago to Madeira are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Madeira?
There is 1 operator available for flights from Chicago to Madeira as of October 2026.
How old do you have to be to fly from Chicago to Madeira?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Madeira.
What documentation or ID do you need to fly to Madeira?
The required travel and health documents for your Madeira trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Madeira. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Madeira

Compare and see reviews for airlines that fly from Chicago to Madeira with momondo

Airline	Rating	Free Cancellation	Price
TAP AIR PORTUGAL	PriceFrom $568	Free Cancellation	Rating 7.2 2,386 reviews		Search TAP AIR PORTUGAL flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Madeira?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Madeira. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Madeira with flexible booking policies on momondo?

Yes. All flights to Madeira from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Madeira?

momondo helps you find the best flight between Chicago and Madeira by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Madeira right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Madeira flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Flights to Lisbonfrom $449

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Flights to Hortafrom $584

Flights to Pico Islandfrom $664

Flights to Porto Santofrom $1,001

Flights to Velasfrom $688

Cheap flights from Chicago to Madeira from $255

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Madeira departing on 11/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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TAP AIR PORTUGAL flights from Chicago to Madeira

Our best TAP AIR PORTUGAL deals on Chicago to Madeira flight tickets

KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets

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How to get the cheapest flight ticket from Chicago to Madeira

What is the cheapest month to fly to Madeira?

Cheap Chicago to Madeira flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago to Madeira

Best airlines flying from Chicago to Madeira

Compare and see reviews for airlines that fly from Chicago to Madeira with momondo

Why use momondo?

An easier way to manage your Madeira trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Madeira

Popular cities in Madeira

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

Madeira flight routes

According to popular flight searches on momondo this year

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According to popular flight searches on momondo this year