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$379+ Cheap flights from Chicago (CHI) to Madeira

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap flight deals from Chicago to Madeira

Keep the following information in mind while searching for Chicago to Madeira flight deals. Data was last updated julio 31, 2025.

Round-trip from

$606
(Iberia)

Popular in

December

Cheapest in

November

Average price

$961
From Chicago (CHI) to Madeira
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chicago to Madeira

Cheapest flights from Chicago to Madeira
Explore the most affordable flight options available from Chicago to Madeira. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This Iberia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/134:30 pmORD - FNC
1 stop13h 55mIberia
lun. 8/257:10 pmFNC - ORD
2 stops27h 15mIberia
Deal found 7/31$605
This oojo deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/58:15 pmORD - FNC
1 stop11h 15mTAP AIR PORTUGAL
vie. 12/127:50 amFNC - ORD
1 stop13h 25mTAP AIR PORTUGAL
Deal found 7/30$611
This Gurufare deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/2210:35 pmORD - FNC
1 stop30h 35mBritish Airways
mar. 9/306:40 pmFNC - ORD
1 stop26h 10mBritish Airways
Deal found 7/29$639
This KLM deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/15:25 pmORD - FNC
1 stop35h 10mKLM
dom. 11/910:10 amFNC - ORD
1 stop34h 10mKLM
Deal found 7/31$661
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/216:00 pmORD - FNC
1 stop11h 40mMultiple Airlines
jue. 10/27:45 amFNC - ORD
2 stops39h 06mMultiple Airlines
Deal found 7/29$688

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
Use the filters below to find and compare flights from Chicago to Madeira that are best for you.

Fly from

Chicago

Fly to

Madeira

Route

Depart

Return

Price

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

mié. 8/13

4:30 pm-12:25 pm

1 stop13h 55m

Funchal Madeira

lun. 8/25

7:10 pm-4:25 pm

2 stops27h 15m

$605

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

lun. 9/22

10:35 pm-11:10 am

1 stop30h 35m

Funchal Madeira

mar. 9/30

6:40 pm-2:50 pm

1 stop26h 10m

$639

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

lun. 9/22

4:40 pm-9:35 am

1 stop34h 55m

Funchal Madeira

mar. 9/30

6:30 pm-4:20 pm

2 stops27h 50m

$674

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

lun. 9/8

6:10 pm-9:00 pm

1 stop20h 50m

Funchal Madeira

mié. 9/17

12:40 pm-10:55 am

1 stop28h 15m

$680

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

dom. 9/21

6:00 pm-11:40 am

1 stop11h 40m

Funchal Madeira

jue. 10/2

7:45 am-4:51 pm

2 stops39h 06m

$688

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

jue. 1/15

7:20 pm-1:45 pm

2 stops36h 25m

$379

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

jue. 1/15

11:50 am-8:00 am

3 stops38h 10m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Chicago to Madeira

Have a flexible travel schedule? Discover the best time to fly to Madeira from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Madeira

What is the cheapest month to book a flight from Chicago to Madeira?

Currently, January is the cheapest month in which you can book a flight from Chicago to Madeira (average of $598). Flying from Chicago to Madeira in June is currently the most expensive (average of $1,089). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Chicago to Madeira?

Reviews of airlines servicing Madeira

Get insights into the airlines that provide service to Madeira. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madeira. Reviews last updated julio 31, 2025.
Read reviews from past customers who have flown KLM, TAP AIR PORTUGAL, and Iberia from Chicago to Madeira. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
KLM
7.8
Good
1,383 reviews

Entertainment

7.1

Comfort

7.7

Boarding

7.8

Food

7.3

Overall

7.8

Crew

8.4

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
KLM
7.8
Good
1,383 reviews
KLM
7.8
Good
1,383 reviews

Entertainment

7.1

Comfort

7.7

Boarding

7.8

Food

7.3

Overall

7.8

Crew

8.4

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
TAP AIR PORTUGAL
7.1
Good
1,933 reviews
KLM
7.8
Good
1,383 reviews

Entertainment

7.1

Comfort

7.7

Boarding

7.8

Food

7.3

Overall

7.8

Crew

8.4

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
Iberia
7.0
Good
2,859 reviews
KLM
7.8
Good
1,383 reviews

Entertainment

7.1

Comfort

7.7

Boarding

7.8

Food

7.3

Overall

7.8

Crew

8.4

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.
British Airways
6.6
Okay
7,222 reviews
KLM
7.8
Good
1,383 reviews

Entertainment

7.1

Comfort

7.7

Boarding

7.8

Food

7.3

Overall

7.8

Crew

8.4

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2025

AMS - BOS

A two and half hour delay caused havoc with all connections. Otherwise on board service was great.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Madeira. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Chicago to Madeira that include hotel bookings?

    Yes. In addition to deals on Chicago to Madeira flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Madeira?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Madeira.

  • Can I find deals for business class flights from Chicago to Madeira?

    Yes. Cheapflights offers flight deals from Chicago to Madeira by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Madeira?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Madeira (average of $598). Flying from Chicago to Madeira in June is currently the most expensive (average of $1,089). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from Chicago to Madeira

Discover the top airline that operate flights from Chicago to Madeira. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$548Average$915FlexibilityNo cancel feeOn-timeN/A

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