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

TAP AIR PORTUGAL, KLM, and Air Canada 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 December 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.

$365 Cheap Flights from Chicago to Madeira in 2025/26

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Find the cheapest flights from Chicago to Madeira

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:25 pm - 9:35 am

ORD

FNC

35h 10m1 stop

10:20 am - 3:20 pm

FNC

ORD

34h 00m1 stop

$486KLM

Mon, Mar 2 - Thu, Mar 12

2:21 pm - 9:35 am

ORD

FNC

37h 14m2 stops

10:20 am - 3:20 pm

FNC

ORD

34h 00m1 stop

$490KLM

Mon, Mar 2 - Thu, Mar 12

4:25 pm - 9:35 am

ORD

FNC

35h 10m1 stop

10:25 am - 10:00 am

FNC

ORD

28h 35m2 stops

$496KLM

Mon, Mar 2 - Wed, Mar 11

2:21 pm - 9:35 am

ORD

FNC

37h 14m2 stops

10:20 am - 4:43 pm

FNC

ORD

35h 23m2 stops

$500KLM

Mon, Mar 2 - Thu, Mar 12

5:53 pm - 9:35 am

ORD

FNC

57h 42m2 stops

10:20 am - 3:20 pm

FNC

ORD

34h 00m1 stop

$501KLM

Sun, Mar 1 - Thu, Mar 12

5:53 pm - 9:35 am

ORD

FNC

57h 42m2 stops

10:20 am - 4:43 pm

FNC

ORD

35h 23m2 stops

$506KLM

Sun, Mar 1 - Thu, Mar 12

4:25 pm - 9:20 am

ORD

FNC

34h 55m1 stop

10:20 am - 2:20 pm

FNC

ORD

34h 00m1 stop

$514KLM

Fri, Jan 16 - Thu, Jan 22

1:55 pm - 5:10 pm

ORD

FNC

21h 15m2 stops

10:20 am - 2:20 pm

FNC

ORD

34h 00m1 stop

$519KLM

Thu, Jan 15 - Thu, Jan 22

4:25 pm - 5:50 pm

ORD

FNC

19h 25m1 stop

10:20 am - 11:56 pm

FNC

ORD

19h 36m2 stops

$524KLM

Fri, Jan 16 - Thu, Jan 22

8:15 pm - 1:40 pm

ORD

FNC

11h 25m1 stop

7:50 am - 3:25 pm

FNC

ORD

13h 35m1 stop

$526TAP AIR PORTUGAL

Fri, Jan 16 - Fri, Jan 23

KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets

KLM

Mar 2

ORD4:25 pmChicago O'Hare Intl

35h 10m

1 stop

FNC9:35 amFunchal Madeira

Mar 12

FNC10:20 amFunchal Madeira

34h 00m

1 stop

ORD3:20 pmChicago O'Hare Intl

$486

Find similar

KLM

Mar 2

ORD2:21 pmChicago O'Hare Intl

37h 14m

2 stops

FNC9:35 amFunchal Madeira

Mar 12

FNC10:20 amFunchal Madeira

34h 00m

1 stop

ORD3:20 pmChicago O'Hare Intl

$490

Find similar

KLM

Mar 2

ORD4:25 pmChicago O'Hare Intl

35h 10m

1 stop

FNC9:35 amFunchal Madeira

Mar 11

FNC10:25 amFunchal Madeira

28h 35m

2 stops

ORD10:00 amChicago O'Hare Intl

$496

Find similar

TAP AIR PORTUGAL flights from Chicago to Madeira

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

TAP AIR PORTUGAL

Jan 16

ORD8:15 pmChicago O'Hare Intl

11h 25m

1 stop

FNC1:40 pmFunchal Madeira

Jan 23

FNC7:50 amFunchal Madeira

13h 35m

1 stop

ORD3:25 pmChicago O'Hare Intl

$526

Find similar

TAP AIR PORTUGAL

Mar 1

ORD8:25 pmChicago O'Hare Intl

14h 25m

1 stop

FNC4:50 pmFunchal Madeira

Mar 11

FNC4:10 amFunchal Madeira

16h 50m

1 stop

ORD4:00 pmChicago O'Hare Intl

$549

Find similar

TAP AIR PORTUGAL

Mar 18

ORD8:10 pmChicago O'Hare Intl

19h 15m

1 stop

FNC8:25 pmFunchal Madeira

Mar 25

FNC7:50 amFunchal Madeira

13h 10m

1 stop

ORD4:00 pmChicago O'Hare Intl

$567

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 3/2

4:25 pm-9:35 am

1 stop35h 10m

Funchal Madeira

Thu 3/12

10:20 am-3:20 pm

1 stop34h 00m

$486

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 3/2

2:21 pm-9:35 am

2 stops37h 14m

Funchal Madeira

Thu 3/12

10:20 am-3:20 pm

1 stop34h 00m

$490

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 3/2

4:25 pm-9:35 am

1 stop35h 10m

Funchal Madeira

Wed 3/11

10:25 am-10:00 am

2 stops28h 35m

$496

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 3/2

2:21 pm-9:35 am

2 stops37h 14m

Funchal Madeira

Thu 3/12

10:20 am-4:43 pm

2 stops35h 23m

$500

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 3/1

5:53 pm-9:35 am

2 stops57h 42m

Funchal Madeira

Thu 3/12

10:20 am-3:20 pm

1 stop34h 00m

$501

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 3/1

5:53 pm-9:35 am

2 stops57h 42m

Funchal Madeira

Thu 3/12

10:20 am-4:43 pm

2 stops35h 23m

$506

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 1/16

4:25 pm-9:20 am

1 stop34h 55m

Funchal Madeira

Thu 1/22

10:20 am-2:20 pm

1 stop34h 00m

$514

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 1/15

1:55 pm-5:10 pm

2 stops21h 15m

Funchal Madeira

Thu 1/22

10:20 am-2:20 pm

1 stop34h 00m

$519

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 1/16

4:25 pm-5:50 pm

1 stop19h 25m

Funchal Madeira

Thu 1/22

10:20 am-11:56 pm

2 stops19h 36m

$524

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 1/16

8:15 pm-1:40 pm

1 stop11h 25m

Funchal Madeira

Fri 1/23

7:50 am-3:25 pm

1 stop13h 35m

$526

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 $608, 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 January instead. Flights to Madeira in January, while not as cheap as those in November, still average around $643.

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.

How far in advance should I book a flight to Madeira?

You are more likely to see cheaper flights to Madeira from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Madeira for around $906 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Madeira from Chicago for as low as $541 on momondo.

Cheap Chicago to Madeira flight deals and tips

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

Fastest flight time	11h 40m
Direct flights	None

The fastest flight from Chicago to Madeira takes 11h 40m

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

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 December 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 2,081 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.