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$286+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$529
(oojo)

One-way from

$286
(Flightnetwork)

Popular in

December

Cheapest in

November

Average price

$1,194
From Chicago (CHI) to Madeira
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One-way flight from Chicago (CHI) to Madeira
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Highest demand for flights based on searches. 1% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($46 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Gurufare deal was found by Cheapflights users on 6/14. 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 11/277:20 pmORD - FNC
2 stops36h 25mScandinavian Airlines
Sat 12/64:10 pmFNC - ORD
1 stop30h 35mScandinavian Airlines
Deal found 6/14$471
This oojo deal was found by Cheapflights users on 6/15. 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.
Thu 9/116:00 pmORD - FNC
1 stop11h 40mTAP AIR PORTUGAL
Wed 9/177:20 pmFNC - ORD
1 stop21h 35mTAP AIR PORTUGAL
Deal found 6/15$529
This Iberia deal was found by Cheapflights users on 6/14. 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.
Sat 8/231:27 pmORD - FNC
2 stops38h 53mIberia
Thu 9/41:05 pmFNC - ORD
1 stop31h 10mIberia
Deal found 6/14$677
This KLM deal was found by Cheapflights users on 6/14. 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 8/254:20 pmORD - FNC
1 stop35h 15mKLM
Mon 9/110:15 amFNC - ORD
1 stop33h 55mKLM
Deal found 6/14$713
This British Airways deal was found by Cheapflights users on 6/14. 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.
Sun 8/248:35 pmORD - FNC
1 stop15h 35mBritish Airways
Tue 9/26:40 pmFNC - ORD
1 stop25h 10mBritish Airways
Deal found 6/14$729
This Mytrip deal was found by Cheapflights users on 6/16. 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.
Fri 10/34:00 pmORD - FNC
3 stops34h 35mMultiple Airlines
Mon 10/132:15 pmFNC - ORD
3 stops33h 18mMultiple Airlines
Deal found 6/16$756
This Lufthansa deal was found by Cheapflights users on 6/15. 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.
Thu 11/204:00 pmORD - FNC
1 stop16h 10mLufthansa
Sun 11/303:00 pmFNC - ORD
1 stop28h 10mLufthansa
Deal found 6/15$889
This SWISS deal was found by Cheapflights users on 6/16. 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.
Thu 11/277:05 pmORD - FNC
1 stop33h 55mSWISS
Sat 12/611:50 amFNC - ORD
1 stop34h 25mSWISS
Deal found 6/16$891
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/1510:00 amORD - FNC
2 stops16h 30mUnited Airlines
Wed 7/2311:30 amFNC - ORD
2 stops14h 46mUnited Airlines
Deal found 6/14$932

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 June 16, 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

Thu 11/27

7:20 pm-1:45 pm

2 stops36h 25m

Funchal Madeira

Sat 12/6

4:10 pm-4:45 pm

1 stop30h 35m

$471

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 9/11

6:00 pm-11:40 am

1 stop11h 40m

Funchal Madeira

Wed 9/17

7:20 pm-10:55 am

1 stop21h 35m

$529

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 8/23

1:27 pm-10:20 am

2 stops38h 53m

Funchal Madeira

Thu 9/4

1:05 pm-2:15 pm

1 stop31h 10m

$677

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 8/25

4:20 pm-9:35 am

1 stop35h 15m

Funchal Madeira

Mon 9/1

10:15 am-2:10 pm

1 stop33h 55m

$713

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 8/24

8:35 pm-6:10 pm

1 stop15h 35m

Funchal Madeira

Tue 9/2

6:40 pm-1:50 pm

1 stop25h 10m

$729

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 10/3

4:00 pm-8:35 am

3 stops34h 35m

Funchal Madeira

Mon 10/13

2:15 pm-5:33 pm

3 stops33h 18m

$756

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 11/20

4:00 pm-2:10 pm

1 stop16h 10m

Funchal Madeira

Sun 11/30

3:00 pm-1:10 pm

1 stop28h 10m

$889

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 11/27

7:05 pm-11:00 am

1 stop33h 55m

Funchal Madeira

Sat 12/6

11:50 am-4:15 pm

1 stop34h 25m

$891

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 7/15

10:00 am-8:30 am

2 stops16h 30m

Funchal Madeira

Wed 7/23

11:30 am-8:16 pm

2 stops14h 46m

$932

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Thu 7/31

6:00 pm-1:15 am

1 stop25h 15m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 19 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 June 16, 2025.
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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
1,361 reviews
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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.
SWISS
7.5
Good
1,628 reviews
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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.
United Airlines
7.4
Good
8,801 reviews
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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.
Turkish Airlines
7.3
Good
3,852 reviews
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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.
Air Canada
7.1
Good
9,554 reviews
KLM
7.8
Good
1,361 reviews

Crew

8.4

Entertainment

7.1

Comfort

7.7

Food

7.2

Overall

7.8

Boarding

7.8

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.

  • 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 $286. However, be on the lookout for offers from KLM and United Airlines, 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

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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$613Average$929FlexibilityNo cancel feeOn-timeN/A

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