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Cheap flights from Chicago to Madeira from $311

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 10/5. 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 - 1:30 am
ORD
-
FNC
25h 30m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 4:05 pm
FNC
-
ORD
16h 15m
1 stop
$629TAP AIR PORTUGAL
Sun, Aug 23 - Sat, Aug 29
TAP AIR PORTUGAL Logo
6:00 pm - 1:30 am
ORD
-
FNC
25h 30m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 4:05 pm
FNC
-
ORD
16h 15m
1 stop
$653TAP AIR PORTUGAL
Sun, Aug 23 - Sat, Aug 29
TAP AIR PORTUGAL Logo
7:00 pm - 3:35 pm
ORD
-
FNC
14h 35m
1 stop
TAP AIR PORTUGAL Logo
9:15 pm - 3:30 pm
FNC
-
ORD
24h 15m
1 stop
$656TAP AIR PORTUGAL
Wed, Nov 11 - Tue, Nov 17
TAP AIR PORTUGAL Logo
6:05 pm - 11:40 am
ORD
-
FNC
11h 35m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:30 pm
FNC
-
ORD
26h 55m
1 stop
$656TAP AIR PORTUGAL
Sat, Oct 10 - Sat, Oct 24
TAP AIR PORTUGAL Logo
8:10 pm - 5:10 pm
ORD
-
FNC
15h 00m
1 stop
TAP AIR PORTUGAL Logo
7:50 am - 3:30 pm
FNC
-
ORD
13h 40m
1 stop
$656TAP AIR PORTUGAL
Fri, Nov 6 - Fri, Nov 13
TAP AIR PORTUGAL Logo
6:00 pm - 6:35 pm
ORD
-
FNC
18h 35m
1 stop
TAP AIR PORTUGAL Logo
7:35 pm - 4:00 pm
FNC
-
ORD
26h 25m
1 stop
$656TAP AIR PORTUGAL
Sun, Sep 27 - Tue, Oct 6
TAP AIR PORTUGAL Logo
7:45 pm - 6:35 pm
ORD
-
FNC
16h 50m
1 stop
TAP AIR PORTUGAL Logo
10:00 pm - 4:00 pm
FNC
-
ORD
24h 00m
1 stop
$656TAP AIR PORTUGAL
Thu, Aug 27 - Thu, Sep 3
TAP AIR PORTUGAL Logo
8:10 pm - 5:10 pm
ORD
-
FNC
15h 00m
1 stop
TAP AIR PORTUGAL Logo
4:10 am - 3:30 pm
FNC
-
ORD
17h 20m
1 stop
$656TAP AIR PORTUGAL
Fri, Nov 13 - Thu, Nov 19
KLM Logo
5:13 pm - 9:35 am
ORD
-
FNC
34h 22m
2 stops
KLM Logo
10:25 am - 2:25 pm
FNC
-
ORD
34h 00m
1 stop
$739KLM
Mon, Nov 9 - Wed, Nov 18
KLM Logo
5:13 pm - 9:35 am
ORD
-
FNC
34h 22m
2 stops
KLM Logo
10:25 am - 11:59 pm
FNC
-
ORD
19h 34m
2 stops
$749KLM
Mon, Nov 9 - Wed, Nov 18

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KLM flights from Chicago to Madeira

Our best KLM deals on Chicago to Madeira flight tickets
KLM
Nov 9
ORD5:13 pmChicago O'Hare Intl
34h 22m
2 stops
FNC9:35 amFunchal Madeira
Nov 18
FNC10:25 amFunchal Madeira
34h 00m
1 stop
ORD2:25 pmChicago O'Hare Intl
$739
KLM
Nov 9
ORD5:13 pmChicago O'Hare Intl
34h 22m
2 stops
FNC9:35 amFunchal Madeira
Nov 18
FNC10:25 amFunchal Madeira
19h 34m
2 stops
ORD11:59 pmChicago O'Hare Intl
$749
KLM
Nov 1
ORD6:14 pmChicago O'Hare Intl
57h 21m
2 stops
FNC9:35 amFunchal Madeira
Nov 18
FNC10:25 amFunchal Madeira
34h 00m
1 stop
ORD2:25 pmChicago O'Hare Intl
$750

TAP AIR PORTUGAL flights from Chicago to Madeira

Our best TAP AIR PORTUGAL deals on Chicago to Madeira flight tickets
TAP AIR PORTUGAL
Aug 23
ORD6:00 pmChicago O'Hare Intl
25h 30m
1 stop
FNC1:30 amFunchal Madeira
Aug 29
FNC5:50 amFunchal Madeira
16h 15m
1 stop
ORD4:05 pmChicago O'Hare Intl
$629
TAP AIR PORTUGAL
Aug 23
ORD6:00 pmChicago O'Hare Intl
25h 30m
1 stop
FNC1:30 amFunchal Madeira
Aug 29
FNC5:50 amFunchal Madeira
16h 15m
1 stop
ORD4:05 pmChicago O'Hare Intl
$653
TAP AIR PORTUGAL
Oct 10
ORD6:05 pmChicago O'Hare Intl
11h 35m
1 stop
FNC11:40 amFunchal Madeira
Oct 24
FNC7:35 pmFunchal Madeira
26h 55m
1 stop
ORD4:30 pmChicago O'Hare Intl
$656

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 July 28, 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 8/23

6:00 pm-1:30 am

1 stop25h 30m

Funchal Madeira

Sat 8/29

5:50 am-4:05 pm

1 stop16h 15m

$629

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 8/23

6:00 pm-1:30 am

1 stop25h 30m

Funchal Madeira

Sat 8/29

5:50 am-4:05 pm

1 stop16h 15m

$653

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 11/11

7:00 pm-3:35 pm

1 stop14h 35m

Funchal Madeira

Tue 11/17

9:15 pm-3:30 pm

1 stop24h 15m

$656

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 10/10

6:05 pm-11:40 am

1 stop11h 35m

Funchal Madeira

Sat 10/24

7:35 pm-4:30 pm

1 stop26h 55m

$656
Quickest round-trip

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 11/6

8:10 pm-5:10 pm

1 stop15h 00m

Funchal Madeira

Fri 11/13

7:50 am-3:30 pm

1 stop13h 40m

$656

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 9/27

6:00 pm-6:35 pm

1 stop18h 35m

Funchal Madeira

Tue 10/6

7:35 pm-4:00 pm

1 stop26h 25m

$656

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 8/27

7:45 pm-6:35 pm

1 stop16h 50m

Funchal Madeira

Thu 9/3

10:00 pm-4:00 pm

1 stop24h 00m

$656

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 11/13

8:10 pm-5:10 pm

1 stop15h 00m

Funchal Madeira

Thu 11/19

4:10 am-3:30 pm

1 stop17h 20m

$656

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 11/9

5:13 pm-9:35 am

2 stops34h 22m

Funchal Madeira

Wed 11/18

10:25 am-2:25 pm

1 stop34h 00m

$739

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 11/9

5:13 pm-9:35 am

2 stops34h 22m

Funchal Madeira

Wed 11/18

10:25 am-11:59 pm

2 stops19h 34m

$749

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 April. Flight prices, which tend to average around $575, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of April, then book flights to Madeira from Chicago during January instead. Flights to Madeira in January, while not as cheap as those in April, still average around $635.

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 35m

Direct flights

None
The fastest flight from Chicago to Madeira takes 11h 35m
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 $569Free CancellationRating
7.2
2,350 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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