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

TAP AIR PORTUGAL is the most popular carrier 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 September 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.

$279 Cheap Flights from Chicago to Madeira in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Madeira

Round-trip

One-way

Last minute

Cheap round-trip flights

9:45 pm - 2:15 pmORD-FNC

34h 30m1 stop

5:10 pm - 6:45 pmFNC-ORD

31h 35m1 stop

$538British Airways

Find Deal

Sun, Nov 23 - Thu, Dec 4

7:10 pm - 5:10 pmORD-FNC

16h 00m1 stop

4:10 am - 3:00 pmFNC-ORD

16h 50m1 stop

$557TAP AIR PORTUGAL

Find Deal

Wed, Dec 3 - Tue, Dec 9

8:15 pm - 5:10 pmORD-FNC

14h 55m1 stop

7:50 am - 3:15 pmFNC-ORD

13h 25m1 stop

$558TAP AIR PORTUGAL

Find Deal

Fri, Dec 5 - Fri, Dec 12

5:10 pm - 3:05 pmORD-FNC

15h 55m1 stop

4:55 pm - 1:50 pmFNC-ORD

26h 55m1 stop

$577British Airways

Find Deal

Tue, Nov 25 - Mon, Dec 1

6:15 pm - 9:30 amORD-FNC

33h 15m2 stops

10:25 am - 4:18 pmFNC-ORD

35h 53m2 stops

$583KLM

Find Deal

Tue, Nov 25 - Mon, Dec 1

6:15 pm - 9:30 amORD-FNC

33h 15m2 stops

10:25 am - 4:18 pmFNC-ORD

35h 53m2 stops

$593KLM

Find Deal

Tue, Nov 25 - Mon, Dec 1

6:45 pm - 10:30 amORD-FNC

33h 45m2 stops

11:10 am - 10:28 pmFNC-ORD

40h 18m2 stops

$627Iberia

Find Deal

Fri, Feb 27 - Sun, Mar 8

4:45 pm - 1:30 pmORD-FNC

14h 45m1 stop

2:10 pm - 2:30 pmFNC-ORD

30h 20m1 stop

$640Iberia

Find Deal

Tue, Nov 4 - Wed, Nov 12

6:50 pm - 5:55 pmORD-FNC

17h 05m2 stops

11:00 am - 4:20 pmFNC-ORD

35h 20m2 stops

$710Multiple Airlines

Find Deal

Tue, Nov 4 - Wed, Nov 12

9:50 pm - 9:15 amORD-FNC

29h 25m3 stops

9:15 pm - 8:05 pmFNC-ORD

28h 50m3 stops

$759Multiple Airlines

Find Deal

Tue, Nov 4 - Wed, Nov 12

Iberia flights from Chicago to Madeira

Our best Iberia deals on Chicago to Madeira flight tickets

Iberia

Feb 27

ORD6:45 pmChicago O'Hare Intl

33h 45m

2 stops

FNC10:30 amFunchal Madeira

Mar 8

FNC11:10 amFunchal Madeira

40h 18m

2 stops

ORD10:28 pmChicago O'Hare Intl

$627

Find similar

Iberia

Nov 4

ORD4:45 pmChicago O'Hare Intl

14h 45m

1 stop

FNC1:30 pmFunchal Madeira

Nov 12

FNC2:10 pmFunchal Madeira

30h 20m

1 stop

ORD2:30 pmChicago O'Hare Intl

$640

Find similar

Iberia

Nov 4

ORD4:45 pmChicago O'Hare Intl

14h 45m

1 stop

FNC1:30 pmFunchal Madeira

Nov 12

FNC2:10 pmFunchal Madeira

33h 35m

2 stops

ORD5:45 pmChicago O'Hare Intl

$650

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

Dec 3

ORD7:10 pmChicago O'Hare Intl

16h 00m

1 stop

FNC5:10 pmFunchal Madeira

Dec 9

FNC4:10 amFunchal Madeira

16h 50m

1 stop

ORD3:00 pmChicago O'Hare Intl

$557

Find similar

TAP AIR PORTUGAL

Dec 5

ORD8:15 pmChicago O'Hare Intl

14h 55m

1 stop

FNC5:10 pmFunchal Madeira

Dec 12

FNC7:50 amFunchal Madeira

13h 25m

1 stop

ORD3:15 pmChicago O'Hare Intl

$558

Find similar

TAP AIR PORTUGAL

Oct 31

ORD9:15 pmChicago O'Hare Intl

14h 55m

1 stop

FNC5:10 pmFunchal Madeira

Nov 9

FNC7:50 amFunchal Madeira

12h 55m

1 stop

ORD2:45 pmChicago O'Hare Intl

$594

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 11/23

9:45 pm-2:15 pm

1 stop34h 30m

Funchal Madeira

Thu 12/4

5:10 pm-6:45 pm

1 stop31h 35m

$538

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 12/3

7:10 pm-5:10 pm

1 stop16h 00m

Funchal Madeira

Tue 12/9

4:10 am-3:00 pm

1 stop16h 50m

$557

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 12/5

8:15 pm-5:10 pm

1 stop14h 55m

Funchal Madeira

Fri 12/12

7:50 am-3:15 pm

1 stop13h 25m

$558

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/25

5:10 pm-3:05 pm

1 stop15h 55m

Funchal Madeira

Mon 12/1

4:55 pm-1:50 pm

1 stop26h 55m

$577

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/25

6:15 pm-9:30 am

2 stops33h 15m

Funchal Madeira

Mon 12/1

10:25 am-4:18 pm

2 stops35h 53m

$583

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/25

6:15 pm-9:30 am

2 stops33h 15m

Funchal Madeira

Mon 12/1

10:25 am-4:18 pm

2 stops35h 53m

$593

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 2/27

6:45 pm-10:30 am

2 stops33h 45m

Funchal Madeira

Sun 3/8

11:10 am-10:28 pm

2 stops40h 18m

$627

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/4

4:45 pm-1:30 pm

1 stop14h 45m

Funchal Madeira

Wed 11/12

2:10 pm-2:30 pm

1 stop30h 20m

$640

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/4

6:50 pm-5:55 pm

2 stops17h 05m

Funchal Madeira

Wed 11/12

11:00 am-4:20 pm

2 stops35h 20m

$710

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 11/4

9:50 pm-9:15 am

3 stops29h 25m

Funchal Madeira

Wed 11/12

9:15 pm-8:05 pm

3 stops28h 50m

$759

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 $655, 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 October instead. Flights to Madeira in October, while not as cheap as those in November, still average around $711.

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

Direct flights	None

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 September 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 $594	Free Cancellation	Rating 7.1 1,991 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.