What is the cheapest airline that flies from Chicago to Madeira?

Iberia, TAP AIR PORTUGAL, and Lufthansa are the most popular carriers operating 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 August 2025.

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.

$306 Cheap Flights from Chicago to Madeira in 2025

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Find the cheapest flights from Chicago to Madeira

Round-trip

One-way

Last minute

Cheap round-trip flights

8:15 pm - 8:25 pmORD-FNC

18h 10m1 stop

4:10 am - 3:15 pmFNC-ORD

17h 05m1 stop

$610TAP AIR PORTUGAL

Find Deal

Fri, Dec 5 - Thu, Dec 11

8:15 pm - 1:00 amORD-FNC

22h 45m1 stop

4:10 am - 3:15 pmFNC-ORD

17h 05m1 stop

$611TAP AIR PORTUGAL

Find Deal

Fri, Dec 5 - Thu, Dec 11

4:15 pm - 9:35 amORD-FNC

35h 20m1 stop

6:30 pm - 2:40 pmFNC-ORD

26h 10m1 stop

$662KLM

Find Deal

Mon, Aug 18 - Tue, Aug 26

4:30 pm - 11:35 amORD-FNC

13h 05m1 stop

1:05 pm - 2:15 pmFNC-ORD

31h 10m1 stop

$664Iberia

Find Deal

Fri, Sep 26 - Thu, Oct 2

4:15 pm - 9:35 amORD-FNC

35h 20m1 stop

6:30 pm - 4:13 pmFNC-ORD

27h 43m2 stops

$672KLM

Find Deal

Mon, Aug 18 - Tue, Aug 26

4:30 pm - 11:35 amORD-FNC

13h 05m1 stop

1:05 pm - 1:30 pmFNC-ORD

30h 25m2 stops

$677Iberia

Find Deal

Fri, Sep 26 - Thu, Oct 2

1:59 pm - 11:35 amORD-FNC

15h 36m2 stops

1:05 pm - 1:30 pmFNC-ORD

30h 25m2 stops

$681Iberia

Find Deal

Fri, Sep 26 - Thu, Oct 2

4:25 pm - 9:35 amORD-FNC

35h 10m1 stop

10:20 am - 11:53 pmFNC-ORD

19h 33m2 stops

$682KLM

Find Deal

Sat, Nov 22 - Thu, Dec 4

4:30 pm - 12:25 pmORD-FNC

13h 55m1 stop

12:00 pm - 6:15 pmFNC-ORD

36h 15m1 stop

$687

Find Deal

Wed, Sep 10 - Wed, Sep 17

6:50 pm - 1:00 amORD-FNC

24h 10m2 stops

7:50 am - 4:20 pmFNC-ORD

38h 30m2 stops

$785

Find Deal

Fri, Nov 21 - Wed, Dec 3

TAP AIR PORTUGAL flights from Chicago to Madeira

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

TAP AIR PORTUGAL

Dec 5

ORD8:15 pmChicago O'Hare Intl

18h 10m

1 stop

FNC8:25 pmFunchal Madeira

Dec 11

FNC4:10 amFunchal Madeira

17h 05m

1 stop

ORD3:15 pmChicago O'Hare Intl

$610

Find similar

TAP AIR PORTUGAL

Dec 5

ORD8:15 pmChicago O'Hare Intl

22h 45m

1 stop

FNC1:00 amFunchal Madeira

Dec 11

FNC4:10 amFunchal Madeira

17h 05m

1 stop

ORD3:15 pmChicago O'Hare Intl

$611

Find similar

TAP AIR PORTUGAL

Nov 21

ORD8:15 pmChicago O'Hare Intl

22h 45m

1 stop

FNC1:00 amFunchal Madeira

Dec 2

FNC4:10 amFunchal Madeira

16h 50m

1 stop

ORD3:00 pmChicago O'Hare Intl

$692

Find similar

KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets

KLM

Aug 18

ORD4:15 pmChicago O'Hare Intl

35h 20m

1 stop

FNC9:35 amFunchal Madeira

Aug 26

FNC6:30 pmFunchal Madeira

26h 10m

1 stop

ORD2:40 pmChicago O'Hare Intl

$662

Find similar

KLM

Aug 18

ORD4:15 pmChicago O'Hare Intl

35h 20m

1 stop

FNC9:35 amFunchal Madeira

Aug 26

FNC6:30 pmFunchal Madeira

27h 43m

2 stops

ORD4:13 pmChicago O'Hare Intl

$672

Find similar

KLM

Nov 22

ORD4:25 pmChicago O'Hare Intl

35h 10m

1 stop

FNC9:35 amFunchal Madeira

Dec 4

FNC10:20 amFunchal Madeira

19h 33m

2 stops

ORD11:53 pmChicago O'Hare Intl

$682

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 12/5

8:15 pm-8:25 pm

1 stop18h 10m

Funchal Madeira

Thu 12/11

4:10 am-3:15 pm

1 stop17h 05m

$610

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 12/5

8:15 pm-1:00 am

1 stop22h 45m

Funchal Madeira

Thu 12/11

4:10 am-3:15 pm

1 stop17h 05m

$611

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 8/18

4:15 pm-9:35 am

1 stop35h 20m

Funchal Madeira

Tue 8/26

6:30 pm-2:40 pm

1 stop26h 10m

$662

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 9/26

4:30 pm-11:35 am

1 stop13h 05m

Funchal Madeira

Thu 10/2

1:05 pm-2:15 pm

1 stop31h 10m

$664

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 8/18

4:15 pm-9:35 am

1 stop35h 20m

Funchal Madeira

Tue 8/26

6:30 pm-4:13 pm

2 stops27h 43m

$672

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 9/26

4:30 pm-11:35 am

1 stop13h 05m

Funchal Madeira

Thu 10/2

1:05 pm-1:30 pm

2 stops30h 25m

$677

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 9/26

1:59 pm-11:35 am

2 stops15h 36m

Funchal Madeira

Thu 10/2

1:05 pm-1:30 pm

2 stops30h 25m

$681

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 11/22

4:25 pm-9:35 am

1 stop35h 10m

Funchal Madeira

Thu 12/4

10:20 am-11:53 pm

2 stops19h 33m

$682

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 9/10

4:30 pm-12:25 pm

1 stop13h 55m

Funchal Madeira

Wed 9/17

12:00 pm-6:15 pm

1 stop36h 15m

$687

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 11/21

6:50 pm-1:00 am

2 stops24h 10m

Funchal Madeira

Wed 12/3

7:50 am-4:20 pm

2 stops38h 30m

$785

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

Prices

Airlines

What is the cheapest month to fly to Madeira?

The cheapest month to fly to Madeira from Chicago is in November. Flight prices, which tend to average around $625, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Madeira from Chicago during March instead. Flights to Madeira in March, while not as cheap as those in November, still average around $705.

What is the cheapest day to depart on your flight to Madeira?

On average, the least expensive day to fly to Madeira from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $869. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $1,342. These prices are subject to change though, so be sure to set up a Price Alert for flights to Madeira.

What is the cheapest time of day to depart on your flight to Madeira?

Flying to Madeira from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $786 when looking at flights departing in the evening. In the afternoon is when there is more demand to fly to Madeira, so prices are often more expensive at around $1,073 per ticket.

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	$306
Fastest flight time	11h 00m
Direct flights	None
Airports in Madeira	1 airport

The best one-way flight to Madeira from Chicago in the past 72 hours is $306. The best round-trip flight deal from Chicago to Madeira found on momondo in the last 72 hours is $610.

The fastest flight from Chicago to Madeira takes 11h 00m

There are no direct flights from Chicago to Madeira. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Funchal Madeira Airport.

There is 1 airport near Madeira: Funchal Madeira (FNC)

Search flight deals

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 August 2025.
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 $548	Free Cancellation	Rating 7.1 1,942 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.