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$411+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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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 November 4, 2025.

This British Airways deal was found by Cheapflights users on 11/2. 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 11/165:10 pmORD - FNC
1 stop17h 05mBritish Airways
Tue 11/253:05 pmFNC - ORD
1 stop28h 45mBritish Airways
Deal found 11/2$483
This oojo deal was found by Cheapflights users on 11/2. 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.
Wed 12/37:10 pmORD - FNC
1 stop16h 00mTAP AIR PORTUGAL
Tue 12/99:15 pmFNC - ORD
1 stop23h 45mTAP AIR PORTUGAL
Deal found 11/2$530
This Ovago deal was found by Cheapflights users on 11/3. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:25 pmORD - FNC
1 stop15h 50mBritish Airways
Tue 12/23:05 pmFNC - ORD
1 stop28h 45mBritish Airways
Deal found 11/3$557
This Booking.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/19:45 pmORD - FNC
1 stop35h 25mBritish Airways
Mon 12/85:05 pmFNC - ORD
1 stop26h 45mBritish Airways
Deal found 11/3$564
This KLM deal was found by Cheapflights users on 11/3. 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.
Sat 12/64:25 pmORD - FNC
1 stop35h 10mKLM
Fri 12/126:00 pmFNC - ORD
1 stop26h 20mKLM
Deal found 11/3$592
This Trip.com deal was found by Cheapflights users on 11/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:20 pmORD - FNC
2 stops19h 15mMultiple Airlines
Tue 12/29:10 pmFNC - ORD
2 stops49h 35mMultiple Airlines
Deal found 11/3$607
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Thu 12/47:05 amORD - FNC
2 stops23h 30mMultiple Airlines
Thu 12/114:05 pmFNC - ORD
2 stops34h 00mMultiple Airlines
Deal found 11/4$626
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Wed 12/310:00 amORD - FNC
2 stops28h 10mMultiple Airlines
Tue 12/99:10 pmFNC - ORD
2 stops22h 00mMultiple Airlines
Deal found 11/2$632

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$424
(KAYAK)

One-way from

$411
(FlightHub)

Popular in

December

Cheapest in

November

Average price

$655
Provider with most accurate pricing for Chicago (CHI)-Funchal Madeira flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Funchal Madeira flights.
Search Deals
From Chicago (CHI) to Madeira
Search Deals
One-way flight from Chicago (CHI) to Madeira
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 4, 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

Sun 11/16

5:10 pm-4:15 pm

1 stop17h 05m

Funchal Madeira

Tue 11/25

3:05 pm-1:50 pm

1 stop28h 45m

$483

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 2/24

5:53 pm-9:30 am

2 stops33h 37m

Funchal Madeira

Thu 3/5

10:20 am-2:20 pm

1 stop34h 00m

$496

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 2/6

7:20 pm-3:20 pm

1 stop14h 00m

Funchal Madeira

Sat 2/14

4:10 pm-4:55 pm

1 stop30h 45m

$500

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Tue 2/24

5:37 pm-9:30 am

2 stops33h 53m

Funchal Madeira

Wed 3/4

10:25 am-5:45 pm

2 stops37h 20m

$506

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Wed 12/3

7:10 pm-5:10 pm

1 stop16h 00m

Funchal Madeira

Tue 12/9

9:15 pm-3:00 pm

1 stop23h 45m

$530

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 1/19

5:54 pm-9:30 am

2 stops57h 36m

Funchal Madeira

Fri 1/30

6:00 pm-2:20 pm

1 stop26h 20m

$532

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sun 2/8

5:54 pm-9:35 am

2 stops57h 41m

Funchal Madeira

Sun 2/15

10:10 am-2:20 pm

1 stop34h 10m

$532

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Mon 1/19

5:10 pm-2:15 pm

1 stop15h 05m

Funchal Madeira

Fri 1/30

5:25 pm-1:50 pm

1 stop26h 25m

$538

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Fri 3/6

4:25 pm-5:50 pm

1 stop19h 25m

Funchal Madeira

Thu 3/12

10:20 am-3:20 pm

1 stop34h 00m

$542

ChicagoFunchal

ORD - FNC

ORDFNC

Chicago O'Hare Intl

Sat 1/24

5:37 pm-9:35 am

2 stops33h 58m

Funchal Madeira

Fri 1/30

6:00 pm-2:20 pm

1 stop26h 20m

$545

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 14 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, October is the cheapest month in which you can book a flight from Chicago to Madeira (average of $475). Flying from Chicago to Madeira in June is currently the most expensive (average of $1,145). 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 November 4, 2025.
Read reviews from past customers who have flown TAP AIR PORTUGAL from Chicago to Madeira. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
TAP AIR PORTUGAL
7.1
Good
2,046 reviews

Overall

7.1

Entertainment

6.3

Boarding

7.0

Food

6.2

Crew

7.8

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

MAD - LIS

Like the onboard attendants I don’t like that they change gate at the last minute And neither the way to get to the airplane by bus, I understand is not airline issue
TAP AIR PORTUGAL
7.1
Good
2,046 reviews
TAP AIR PORTUGAL
7.1
Good
2,046 reviews

Overall

7.1

Entertainment

6.3

Boarding

7.0

Food

6.2

Crew

7.8

Comfort

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2025

MAD - LIS

Like the onboard attendants I don’t like that they change gate at the last minute And neither the way to get to the airplane by bus, I understand is not airline issue

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.

  • How long is the flight from Chicago to Madeira?

    For as low as $500, British Airways can have you in Madeira from Chicago in 14h. The distance between Chicago and Madeira is about 3845 mi. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Madeira (average of $475). Flying from Chicago to Madeira in June is currently the most expensive (average of $1,145). 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$548Average$904FlexibilityNo cancel feeOn-timeN/A

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