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Cheap flights from Chicago to Madeira from $327

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 10/17. 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

Discover deals from 900+ travel sites with momondo.

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
6:00 pm - 1:10 pm
ORD
-
FNC
13h 10m
1 stop
TAP AIR PORTUGAL Logo
6:10 pm - 4:30 pm
FNC
-
ORD
27h 20m
1 stop
$796TAP AIR PORTUGAL
Sun, Oct 18 - Thu, Oct 29
TAP AIR PORTUGAL Logo
6:00 pm - 3:35 pm
ORD
-
FNC
15h 35m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$809TAP AIR PORTUGAL
Wed, Sep 9 - Tue, Sep 15
TAP AIR PORTUGAL Logo
6:05 pm - 11:40 am
ORD
-
FNC
11h 35m
1 stop
TAP AIR PORTUGAL Logo
9:25 am - 4:05 pm
FNC
-
ORD
12h 40m
1 stop
$817TAP AIR PORTUGAL
Sat, Sep 5 - Sat, Sep 12
TAP AIR PORTUGAL Logo
6:00 pm - 12:10 am
ORD
-
FNC
24h 10m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 4:00 pm
FNC
-
ORD
24h 05m
1 stop
$829TAP AIR PORTUGAL
Thu, Sep 10 - Tue, Sep 15
TAP AIR PORTUGAL Logo
6:00 pm - 1:15 pm
ORD
-
FNC
13h 15m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$842TAP AIR PORTUGAL
Fri, Oct 2 - Tue, Oct 6
TAP AIR PORTUGAL Logo
6:00 pm - 2:00 pm
ORD
-
FNC
14h 00m
1 stop
TAP AIR PORTUGAL Logo
4:05 am - 4:00 pm
FNC
-
ORD
17h 55m
1 stop
$844TAP AIR PORTUGAL
Wed, Sep 16 - Sun, Sep 20
TAP AIR PORTUGAL Logo
6:00 pm - 1:15 pm
ORD
-
FNC
13h 15m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$862TAP AIR PORTUGAL
Fri, Sep 25 - Sat, Oct 3
TAP AIR PORTUGAL Logo
6:00 pm - 11:20 pm
ORD
-
FNC
23h 20m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 4:05 pm
FNC
-
ORD
16h 15m
1 stop
$864TAP AIR PORTUGAL
Sun, Sep 6 - Sat, Sep 12
TAP AIR PORTUGAL Logo
4:45 pm - 8:20 am
ORD
-
FNC
33h 35m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 12:40 pm
FNC
-
ORD
20h 45m
1 stop
$880TAP AIR PORTUGAL
Thu, Jul 9 - Wed, Jul 15
TAP AIR PORTUGAL Logo
4:45 pm - 8:20 am
ORD
-
FNC
33h 35m
1 stop
TAP AIR PORTUGAL Logo
9:55 pm - 12:40 pm
FNC
-
ORD
20h 45m
1 stop
$883TAP AIR PORTUGAL
Thu, Jul 9 - Wed, Jul 15

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KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets
KLM
Oct 19
ORD4:50 pmChicago O'Hare Intl
34h 45m
1 stop
FNC9:35 amFunchal Madeira
Oct 30
FNC6:00 pmFunchal Madeira
26h 25m
1 stop
ORD3:25 pmChicago O'Hare Intl
$946
KLM
Oct 20
ORD5:20 pmChicago O'Hare Intl
33h 55m
2 stops
FNC9:15 amFunchal Madeira
Oct 30
FNC6:00 pmFunchal Madeira
26h 25m
1 stop
ORD3:25 pmChicago O'Hare Intl
$950
KLM
Oct 19
ORD4:50 pmChicago O'Hare Intl
34h 45m
1 stop
FNC9:35 amFunchal Madeira
Oct 30
FNC6:00 pmFunchal Madeira
27h 49m
2 stops
ORD4:49 pmChicago O'Hare Intl
$956

TAP AIR PORTUGAL flights from Chicago to Madeira

Our best TAP AIR PORTUGAL deals on Chicago to Madeira flight tickets
TAP AIR PORTUGAL
Oct 18
ORD6:00 pmChicago O'Hare Intl
13h 10m
1 stop
FNC1:10 pmFunchal Madeira
Oct 29
FNC6:10 pmFunchal Madeira
27h 20m
1 stop
ORD4:30 pmChicago O'Hare Intl
$796
TAP AIR PORTUGAL
Sep 9
ORD6:00 pmChicago O'Hare Intl
15h 35m
1 stop
FNC3:35 pmFunchal Madeira
Sep 15
FNC9:55 pmFunchal Madeira
24h 05m
1 stop
ORD4:00 pmChicago O'Hare Intl
$809
TAP AIR PORTUGAL
Sep 5
ORD6:05 pmChicago O'Hare Intl
11h 35m
1 stop
FNC11:40 amFunchal Madeira
Sep 12
FNC9:25 amFunchal Madeira
12h 40m
1 stop
ORD4:05 pmChicago O'Hare Intl
$817

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 June 14, 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 10/18

6:00 pm-1:10 pm

1 stop13h 10m

Funchal Madeira

Thu 10/29

6:10 pm-4:30 pm

1 stop27h 20m

$796

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 9/9

6:00 pm-3:35 pm

1 stop15h 35m

Funchal Madeira

Tue 9/15

9:55 pm-4:00 pm

1 stop24h 05m

$809
Quickest round-trip

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 9/5

6:05 pm-11:40 am

1 stop11h 35m

Funchal Madeira

Sat 9/12

9:25 am-4:05 pm

1 stop12h 40m

$817

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 9/10

6:00 pm-12:10 am

1 stop24h 10m

Funchal Madeira

Tue 9/15

9:55 pm-4:00 pm

1 stop24h 05m

$829

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 10/2

6:00 pm-1:15 pm

1 stop13h 15m

Funchal Madeira

Tue 10/6

7:35 pm-4:00 pm

1 stop26h 25m

$842

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 9/16

6:00 pm-2:00 pm

1 stop14h 00m

Funchal Madeira

Sun 9/20

4:05 am-4:00 pm

1 stop17h 55m

$844

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 9/25

6:00 pm-1:15 pm

1 stop13h 15m

Funchal Madeira

Sat 10/3

7:35 pm-4:00 pm

1 stop26h 25m

$862

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 9/6

6:00 pm-11:20 pm

1 stop23h 20m

Funchal Madeira

Sat 9/12

5:50 am-4:05 pm

1 stop16h 15m

$864

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 7/9

4:45 pm-8:20 am

1 stop33h 35m

Funchal Madeira

Wed 7/15

9:55 pm-12:40 pm

1 stop20h 45m

$880

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 7/9

4:45 pm-8:20 am

1 stop33h 35m

Funchal Madeira

Wed 7/15

9:55 pm-12:40 pm

1 stop20h 45m

$883

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 November. Flight prices, which tend to average around $462, 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 $475.

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.
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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?

  • 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 $545Free CancellationRating
7.2
2,273 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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