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Cheap flights from Chicago to Madeira from $362

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 3/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago to Madeira

Cheap round-trip flights

Enter your travel dates to find the best prices.
TAP AIR PORTUGAL Logo
9:25 pm - 1:00 am
ORD
-
FNC
22h 35m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$575TAP AIR PORTUGAL
Sun, Mar 22 - Tue, Mar 31
TAP AIR PORTUGAL Logo
6:00 pm - 9:05 pm
ORD
-
FNC
21h 05m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$611TAP AIR PORTUGAL
Sun, Apr 26 - Thu, May 7
Multiple Airlines Logo
7:25 pm - 12:55 am
ORD
-
FNC
23h 30m
2 stops
Multiple Airlines Logo
6:05 am - 6:15 pm
FNC
-
ORD
18h 10m
2 stops
$617Multiple Airlines
Sat, Apr 25 - Thu, May 7
TAP AIR PORTUGAL Logo
6:05 pm - 1:15 pm
ORD
-
FNC
13h 10m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$630TAP AIR PORTUGAL
Sat, Apr 25 - Thu, May 7
TAP AIR PORTUGAL Logo
6:05 pm - 12:10 am
ORD
-
FNC
24h 05m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$632TAP AIR PORTUGAL
Sat, Apr 25 - Thu, May 7
TAP AIR PORTUGAL Logo
6:00 pm - 1:15 pm
ORD
-
FNC
13h 15m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:00 pm
FNC
-
ORD
17h 55m
1 stop
$645TAP AIR PORTUGAL
Wed, Apr 15 - Wed, Apr 22
TAP AIR PORTUGAL Logo
6:00 pm - 1:15 pm
ORD
-
FNC
13h 15m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:00 pm
FNC
-
ORD
17h 55m
1 stop
$646TAP AIR PORTUGAL
Wed, Apr 15 - Wed, Apr 22
TAP AIR PORTUGAL Logo
6:05 pm - 11:40 am
ORD
-
FNC
11h 35m
1 stop
TAP AIR PORTUGAL Logo
10:00 pm - 4:00 pm
FNC
-
ORD
24h 00m
1 stop
$666TAP AIR PORTUGAL
Sat, Apr 25 - Thu, May 7
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pm
ORD
-
FNC
18h 35m
1 stop
TAP AIR PORTUGAL Logo
9:25 am - 4:00 pm
FNC
-
ORD
12h 35m
1 stop
$672TAP AIR PORTUGAL
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
7:25 pm - 12:55 am
ORD
-
FNC
23h 30m
2 stops
Multiple Airlines Logo
10:45 pm - 11:07 pm
FNC
-
ORD
30h 22m
3 stops
$686Multiple Airlines
Sat, Apr 25 - Thu, May 7

TAP AIR PORTUGAL flights from Chicago to Madeira

Our best TAP AIR PORTUGAL deals on Chicago to Madeira flight tickets
TAP AIR PORTUGAL
Mar 22
ORD9:25 pmChicago O'Hare Intl
22h 35m
1 stop
FNC1:00 amFunchal Madeira
Mar 31
FNC9:55 pmFunchal Madeira
24h 05m
1 stop
ORD4:00 pmChicago O'Hare Intl
$575
TAP AIR PORTUGAL
Apr 26
ORD6:00 pmChicago O'Hare Intl
21h 05m
1 stop
FNC9:05 pmFunchal Madeira
May 7
FNC9:55 pmFunchal Madeira
24h 05m
1 stop
ORD4:00 pmChicago O'Hare Intl
$611
TAP AIR PORTUGAL
Apr 25
ORD6:05 pmChicago O'Hare Intl
13h 10m
1 stop
FNC1:15 pmFunchal Madeira
May 7
FNC7:35 pmFunchal Madeira
26h 25m
1 stop
ORD4:00 pmChicago O'Hare Intl
$630

British Airways flights from Chicago to Madeira

Our best British Airways deals on Chicago to Madeira flight tickets
British Airways
Apr 28
ORD9:15 pmChicago O'Hare Intl
33h 10m
1 stop
FNC12:25 pmFunchal Madeira
May 5
FNC7:35 pmFunchal Madeira
24h 15m
1 stop
ORD1:50 pmChicago O'Hare Intl
$713
British Airways
Apr 21
ORD9:15 pmChicago O'Hare Intl
33h 10m
1 stop
FNC12:25 pmFunchal Madeira
Apr 30
FNC1:15 pmFunchal Madeira
30h 35m
1 stop
ORD1:50 pmChicago O'Hare Intl
$766
British Airways
May 1
ORD9:15 pmChicago O'Hare Intl
33h 20m
1 stop
FNC12:35 pmFunchal Madeira
May 8
FNC1:10 pmFunchal Madeira
30h 40m
1 stop
ORD1:50 pmChicago O'Hare Intl
$818

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Madeira that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 10, 2026.
Use the filters below to find and compare flights from Chicago to Madeira that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 3/22

9:25 pm-1:00 am

1 stop22h 35m

Funchal Madeira

Tue 3/31

9:55 pm-4:00 pm

1 stop24h 05m

$575

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 4/26

6:00 pm-9:05 pm

1 stop21h 05m

Funchal Madeira

Thu 5/7

9:55 pm-4:00 pm

1 stop24h 05m

$611

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 4/25

7:25 pm-12:55 am

2 stops23h 30m

Funchal Madeira

Thu 5/7

6:05 am-6:15 pm

2 stops18h 10m

$617

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 4/25

6:05 pm-1:15 pm

1 stop13h 10m

Funchal Madeira

Thu 5/7

7:35 pm-4:00 pm

1 stop26h 25m

$630

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 4/25

6:05 pm-12:10 am

1 stop24h 05m

Funchal Madeira

Thu 5/7

7:35 pm-4:00 pm

1 stop26h 25m

$632
Quickest round-trip

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 4/15

6:00 pm-1:15 pm

1 stop13h 15m

Funchal Madeira

Wed 4/22

4:05 am-4:00 pm

1 stop17h 55m

$645

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 4/15

6:00 pm-1:15 pm

1 stop13h 15m

Funchal Madeira

Wed 4/22

4:05 am-4:00 pm

1 stop17h 55m

$646

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 4/25

6:05 pm-11:40 am

1 stop11h 35m

Funchal Madeira

Thu 5/7

10:00 pm-4:00 pm

1 stop24h 00m

$666

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 4/15

6:00 pm-6:35 pm

1 stop18h 35m

Funchal Madeira

Wed 4/22

9:25 am-4:00 pm

1 stop12h 35m

$672

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 4/25

7:25 pm-12:55 am

2 stops23h 30m

Funchal Madeira

Thu 5/7

10:45 pm-11:07 pm

3 stops30h 22m

$686

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Madeira from

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 $550, 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 November instead. Flights to Madeira in November, while not as cheap as those in January, still average around $608.

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 $873 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 $650 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

12h 25m

Direct flights

None
The fastest flight from Chicago to Madeira takes 12h 25m
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?

  • 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 PORTUGALPriceFrom $548Free CancellationRating
7.1
2,163 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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