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$371+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$598
(flugladen.de)

Popular in

December

Cheapest in

November

Average price

$1,339
Provider with most accurate pricing for Chicago (CHI)-Funchal Madeira flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Funchal Madeira flights.
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From Chicago (CHI) to Madeira
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($42 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This flugladen.de deal was found by Cheapflights users on 4/30. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/510:25 pmORD - FNC
1 stop30h 45mMultiple Airlines
Tue 5/136:40 pmFNC - ORD
1 stop23h 05mMultiple Airlines
Deal found 4/30$598
This British Airways deal was found by Cheapflights users on 5/1. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/55:40 pmORD - FNC
1 stop18h 10mBritish Airways
Tue 5/136:40 pmFNC - ORD
1 stop23h 05mBritish Airways
Deal found 5/1$641
This Iberia deal was found by Cheapflights users on 4/30. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/244:30 pmORD - FNC
1 stop13h 05mIberia
Sun 11/211:10 amFNC - ORD
2 stops38h 35mIberia
Deal found 4/30$658
This KLM deal was found by Cheapflights users on 4/30. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/56:15 pmORD - FNC
2 stops17h 30mKLM
Tue 5/136:30 pmFNC - ORD
1 stop26h 10mKLM
Deal found 4/30$661
This oojo deal was found by Cheapflights users on 4/30. 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.
Fri 10/246:00 pmORD - FNC
1 stop13h 25mTAP AIR PORTUGAL
Sun 11/27:50 amFNC - ORD
1 stop13h 10mTAP AIR PORTUGAL
Deal found 4/30$716
This SWISS deal was found by Cheapflights users on 4/30. 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 SWISS is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:05 pmORD - FNC
1 stop32h 35mSWISS
Wed 5/2110:25 amFNC - ORD
1 stop35h 30mSWISS
Deal found 4/30$820
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/82:20 pmORD - FNC
1 stop12h 10mUnited Airlines
Fri 7/1811:30 amFNC - ORD
1 stop13h 10mUnited Airlines
Deal found 4/30$922
This Gurufare deal was found by Cheapflights users on 4/30. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/273:55 pmORD - FNC
1 stop16h 15mLufthansa
Fri 12/53:00 pmFNC - ORD
1 stop28h 25mLufthansa
Deal found 4/30$955

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 May 1, 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

Fri 10/24

4:30 pm-11:35 am

1 stop13h 05m

Funchal Madeira

Sun 11/2

11:10 am-7:45 pm

2 stops38h 35m

$658

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 10/24

6:00 pm-1:25 pm

1 stop13h 25m

Funchal Madeira

Sun 11/2

7:50 am-3:00 pm

1 stop13h 10m

$716

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 7/6

7:15 pm-6:10 pm

1 stop16h 55m

Funchal Madeira

Wed 7/16

12:00 pm-1:55 pm

1 stop31h 55m

$744

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 6/10

4:20 pm-9:20 am

1 stop35h 00m

Funchal Madeira

Wed 6/18

10:20 am-2:10 pm

1 stop33h 50m

$787

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 5/14

7:05 pm-9:40 am

1 stop32h 35m

Funchal Madeira

Wed 5/21

10:25 am-3:55 pm

1 stop35h 30m

$820

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 6/10

10:00 am-3:35 pm

2 stops23h 35m

Funchal Madeira

Wed 6/18

7:30 pm-9:56 pm

2 stops32h 26m

$829

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 9/27

4:00 pm-3:10 pm

1 stop17h 10m

Funchal Madeira

Mon 10/6

3:30 pm-12:55 pm

1 stop27h 25m

$848

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 7/8

2:20 pm-8:30 am

1 stop12h 10m

Funchal Madeira

Fri 7/18

11:30 am-6:40 pm

1 stop13h 10m

$922

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 10/5

7:25 pm-2:10 pm

2 stops36h 45m

$371

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 10/5

6:00 pm-1:05 pm

1 stop13h 05m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 15 results
1
2

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.

Rainfall in Madeira by month

Plan your trip to Madeira by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madeira ranges from 0.1 - 4.3 inches per month. December is typically the wettest month, when rainfall can reach 4.3 in. July is typically the driest time to visit Madeira when rainfall is around 0.1 in.

Temperature in Madeira by month

Plan your trip to Madeira by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madeira, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
To help decide which airline to fly from Chicago to Madeira, see what other customers have to say about KLM, SWISS and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.
KLM
7.8
Good
1,334 reviews
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.
SWISS
7.5
Good
1,589 reviews
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.
United Airlines
7.4
Good
8,696 reviews
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.
TAP AIR PORTUGAL
7.1
Good
1,852 reviews
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.
Air Canada
7.0
Good
9,252 reviews
KLM
7.8
Good
1,334 reviews

Entertainment

7.1

Overall

7.8

Food

7.2

Comfort

7.7

Crew

8.4

Boarding

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

LBA - AMS

Overall, the flight from Leeds Bradford to Amsterdam was at expected. The crew were efficient at boarding and professional on board. The only issue was extremely slow check in at Leeds Bradford which was very frustrating.

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$614Average$928FlexibilityNo cancel feeOn-timeN/A

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