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$419+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$719
(KLM)

One-way from

$419
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$1,053
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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One-way flight 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 April 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 April 22, 2025.

This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:15 pmORD - FNC
1 stop13h 40mTAP AIR PORTUGAL
Tue 10/79:50 pmFNC - ORD
1 stop24h 20mTAP AIR PORTUGAL
Deal found 4/22$667
This KLM deal was found by Cheapflights users on 4/20. 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 6/304:20 pmORD - FNC
1 stop35h 15mKLM
Sun 8/246:30 pmFNC - ORD
1 stop25h 40mKLM
Deal found 4/20$719
This Iberia deal was found by Cheapflights users on 4/22. 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 4/22$738
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/65:25 pmORD - FNC
2 stops59h 45mBritish Airways
Wed 7/1612:00 pmFNC - ORD
1 stop36h 15mBritish Airways
Deal found 4/22$788
This Mytrip deal was found by Cheapflights users on 4/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/203:50 pmORD - FNC
2 stops21h 10mMultiple Airlines
Tue 5/279:00 amFNC - ORD
2 stops16h 55mMultiple Airlines
Deal found 4/20$796
This SWISS deal was found by Cheapflights users on 4/22. 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 4/22$821
This Lufthansa deal was found by Cheapflights users on 4/22. 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:00 pmORD - FNC
1 stop16h 40mLufthansa
Mon 10/63:30 pmFNC - ORD
1 stop34h 25mLufthansa
Deal found 4/22$851
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Thu 7/33:40 pmORD - FNC
1 stop11h 05mUnited Airlines
Fri 8/2211:30 amFNC - ORD
1 stop12h 59mUnited Airlines
Deal found 4/20$857
This Air Canada deal was found by Cheapflights users on 4/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:40 amORD - FNC
2 stops20h 45mAir Canada
Tue 10/79:55 amFNC - ORD
2 stops15h 34mAir Canada
Deal found 4/22$1,093

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 April 22, 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

Sat 9/27

6:15 pm-1:55 pm

1 stop13h 40m

Funchal Madeira

Tue 10/7

9:50 pm-4:10 pm

1 stop24h 20m

$667

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 6/30

4:20 pm-9:35 am

1 stop35h 15m

Funchal Madeira

Sun 8/24

6:30 pm-2:10 pm

1 stop25h 40m

$719

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 7/6

5:25 pm-11:10 am

2 stops59h 45m

Funchal Madeira

Wed 7/16

12:00 pm-6:15 pm

1 stop36h 15m

$788

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 5/20

3:50 pm-7:00 pm

2 stops21h 10m

Funchal Madeira

Tue 5/27

9:00 am-7:55 pm

2 stops16h 55m

$796

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

$821

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 9/29

4:00 pm-2:40 pm

1 stop16h 40m

Funchal Madeira

Mon 10/6

3:30 pm-7:55 pm

1 stop34h 25m

$851

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 7/3

3:40 pm-8:45 am

1 stop11h 05m

Funchal Madeira

Wed 8/20

11:30 am-5:00 pm

1 stop11h 30m

$857

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 9/25

10:40 am-1:25 pm

2 stops20h 45m

Funchal Madeira

Tue 10/7

9:55 am-7:29 pm

2 stops15h 34m

$1,093

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 7/9

4:30 pm-12:25 pm

1 stop13h 55m

Funchal Madeira

Tue 7/15

3:50 pm-1:30 pm

2 stops27h 40m

$1,129

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 5/5

7:25 pm-2:00 pm

3 stops36h 35m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 17 results
1
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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 April 22, 2025.
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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
1,331 reviews
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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
1,582 reviews
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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
8,683 reviews
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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.
Turkish Airlines
7.3
Good
3,773 reviews
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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
1,844 reviews
KLM
7.8
Good
1,331 reviews

Comfort

7.7

Entertainment

7.1

Overall

7.8

Crew

8.4

Food

7.3

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.

  • What are the cheapest airlines to fly from Chicago to Madeira one-way?

    The cheapest airline one-way is TAP AIR PORTUGAL, with whom users have recently found tickets for as low as $503. However, be on the lookout for offers from KLM and SWISS, as they are both options that can get you from Chicago to Madeira for a low price.

  • 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

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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$614Average$927FlexibilityNo cancel feeOn-timeN/A

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