$453+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
May 3 — May 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Madeira with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Madeira
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MadeiraExplore 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 3, 2026.
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 3, 2026.
This Gotogate deal was found by Cheapflights users on 3/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 pm
ORD
- FNC
1 stop21h 05m
TAP AIR PORTUGAL
Tue 4/289:55 pm
FNC
- ORD
1 stop24h 05m
TAP AIR PORTUGAL
Deal found 3/30![TAP AIR PORTUGAL logo]()
$654
This oojo deal was found by Cheapflights users on 4/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:10 pm
ORD
- FNC
1 stop15h 00m
TAP AIR PORTUGAL
Sun 11/157:55 am
FNC
- ORD
1 stop13h 05m
TAP AIR PORTUGAL
Deal found 4/1![TAP AIR PORTUGAL logo]()
$669
This Trip.com deal was found by Cheapflights users on 3/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:20 pm
ORD
- FNC
2 stops19h 10m
Multiple Airlines
Sun 12/69:25 am
FNC
- ORD
2 stops37h 20m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$674
This oojo deal was found by Cheapflights users on 3/30. 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.
Sun 4/196:00 pm
ORD
- FNC
1 stop21h 05m
TAP AIR PORTUGAL
Sun 4/264:05 am
FNC
- ORD
1 stop17h 55m
TAP AIR PORTUGAL
Deal found 3/30![TAP AIR PORTUGAL logo]()
$714
This oojo deal was found by Cheapflights users on 3/30. 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.
Sun 5/36:00 pm
ORD
- FNC
1 stop23h 20m
TAP AIR PORTUGAL
Fri 5/159:55 pm
FNC
- ORD
1 stop24h 10m
TAP AIR PORTUGAL
Deal found 3/30![TAP AIR PORTUGAL logo]()
$724
This oojo deal was found by Cheapflights users on 4/2. 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 4/156:00 pm
ORD
- FNC
1 stop15h 35m
TAP AIR PORTUGAL
Wed 4/224:05 am
FNC
- ORD
1 stop17h 55m
TAP AIR PORTUGAL
Deal found 4/2![TAP AIR PORTUGAL logo]()
$729
This Iberia deal was found by Cheapflights users on 3/31. 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.
Sun 4/194:55 pm
ORD
- FNC
1 stop13h 45m
Multiple Airlines
Tue 4/287:35 pm
FNC
- ORD
2 stops32h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$767
This oojo deal was found by Cheapflights users on 4/2. 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.
Sun 12/68:15 pm
ORD
- FNC
1 stop14h 35m
TAP AIR PORTUGAL
Thu 12/106:10 pm
FNC
- ORD
1 stop27h 20m
TAP AIR PORTUGAL
Deal found 4/2![TAP AIR PORTUGAL logo]()
$769
Best flights from Chicago to MadeiraDiscover carefully curated flight deals from Chicago to Madeira that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
Discover carefully curated flight deals from Chicago to Madeira that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
This British Airways deal was found by Cheapflights users on 3/30. 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 British Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:45 pm
ORD
- FNC
2 stops18h 20m
British Airways
Tue 4/287:35 pm
FNC
- ORD
1 stop26h 20m
British Airways
Deal found 3/30![British Airways logo]()
$805
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:55 pm
ORD
- FNC
1 stop35h 40m
Multiple Airlines
Tue 4/2812:25 pm
FNC
- ORD
1 stop32h 30m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$970
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:22 am
ORD
- FNC
2 stops19h 03m
Iberia
Wed 5/201:35 pm
FNC
- ORD
1 stop32h 25m
Iberia
Deal found 3/29![Iberia logo]()
$998
This TAP AIR PORTUGAL deal was found by Cheapflights users on 3/29. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:55 pm
ORD
- FNC
2 stops18h 15m
TAP AIR PORTUGAL
Sun 6/218:45 am
FNC
- ORD
2 stops31h 21m
TAP AIR PORTUGAL
Deal found 3/29![TAP AIR PORTUGAL logo]()
$1,298
This Iberia deal was found by Cheapflights users on 3/29. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:22 am
ORD
- FNC
2 stops19h 03m
Multiple Airlines
Wed 5/201:35 pm
FNC
- ORD
2 stops32h 18m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$1,100
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1510:30 pm
ORD
- FNC
2 stops44h 25m
Multiple Airlines
Fri 5/229:25 am
FNC
- ORD
1 stop12h 35m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$1,310
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Mon 4/610:55 am
ORD
- FNC
2 stops16h 05m
Multiple Airlines
Sun 4/125:15 am
FNC
- ORD
3 stops43h 16m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$1,371
This Iberia deal was found by Cheapflights users on 4/3. 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1111:22 am
ORD
- FNC
2 stops17h 18m
Multiple Airlines
Thu 4/161:05 pm
FNC
- ORD
2 stops25h 57m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$1,375
Last-minute flights from Chicago to MadeiraDiscover last-minute flight deals from Chicago to Madeira. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Madeira. Data last updated April 3, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Thu 4/912:50 pm
ORD
- FNC
3 stops23h 45m
Multiple Airlines
Mon 4/137:35 pm
FNC
- ORD
3 stops29h 50m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$1,311
This oojo deal was found by Cheapflights users on 3/31. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 pm
ORD
- FNC
1 stop13h 10m
TAP AIR PORTUGAL
Thu 4/169:55 pm
FNC
- ORD
1 stop24h 05m
TAP AIR PORTUGAL
Deal found 3/31![TAP AIR PORTUGAL logo]()
$819
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 pm
ORD
- FNC
1 stop13h 10m
Multiple Airlines
Thu 4/163:05 pm
FNC
- ORD
2 stops48h 00m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$917
One-way flights from Chicago to MadeiraSearch for one-way flight options from Chicago to Madeira. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
Search for one-way flight options from Chicago to Madeira. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:05 pm
ORD
- FNC
1 stop13h 10m
TAP AIR PORTUGAL
Deal found 4/1![TAP AIR PORTUGAL logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/19:48 pm
ORD
- FNC
2 stops45h 27m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/313:45 pm
ORD
- FNC
3 stops45h 55m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$511
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:25 am
ORD
- FNC
3 stops23h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 3/29. 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.
Sat 6/611:09 am
ORD
- FNC
3 stops19h 16m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$625
This FlightHub deal was found by Cheapflights users on 3/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:05 pm
ORD
- FNC
1 stop11h 35m
TAP AIR PORTUGAL
Deal found 3/29![TAP AIR PORTUGAL logo]()
$901
Find 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 3, 2026.
Round-trip from | $654 (Gotogate) |
|---|---|
One-way from | $453 (Booking.com) |
Popular in | June |
Cheapest in | January |
Average price | $685 |
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 3, 2026.
Use the filters below to find and compare flights from Chicago to Madeira that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sun 4/19
5:45 pm-6:05 pm
2 stops18h 20m
Funchal Madeira
Tue 4/28
7:35 pm-3:55 pm
1 stop26h 20m
$805
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sun 4/19
5:55 pm-11:35 am
1 stop35h 40m
Funchal Madeira
Tue 4/28
12:25 pm-2:55 pm
1 stop32h 30m
$970
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Wed 5/13
11:22 am-12:25 pm
2 stops19h 03m
Funchal Madeira
Wed 5/20
1:35 pm-4:00 pm
1 stop32h 25m
$998
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Wed 5/13
11:22 am-12:25 pm
2 stops19h 03m
Funchal Madeira
Wed 5/20
1:35 pm-3:53 pm
2 stops32h 18m
$1,100
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sat 6/13
1:55 pm-2:10 pm
2 stops18h 15m
Funchal Madeira
Sun 6/21
8:45 am-10:06 am
2 stops31h 21m
$1,298
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Fri 5/15
10:30 pm-12:55 am
2 stops44h 25m
Funchal Madeira
Fri 5/22
9:25 am-4:00 pm
1 stop12h 35m
$1,310
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Mon 4/6
10:55 am-9:00 am
2 stops16h 05m
Funchal Madeira
Sun 4/12
5:15 am-6:31 pm
3 stops43h 16m
$1,371
Quickest round-trip
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sat 4/11
11:22 am-10:40 am
2 stops17h 18m
Funchal Madeira
Thu 4/16
1:05 pm-9:02 am
2 stops25h 57m
$1,375
Cheapest one-way
Quickest one-way
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sat 8/1
6:05 pm-1:15 pm
1 stop13h 10m
$453
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Fri 7/31
6:00 pm-6:35 pm
1 stop18h 35m
$511
Showing 1-10 of 15 resultsSorted by cheapest first
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.
ORD-FNC
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
CHI-PTMA
ORD-FNC
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 $865). 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 April 3, 2026.
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.
Food
6.2
Overall
7.1
Entertainment
6.3
Crew
7.8
Boarding
7.0
Comfort
7.1
Reviews
1 / 20
8.0
ExcellentMichael,Dec 2025
FNC - LIS
Food
6.2
Overall
7.1
Entertainment
6.3
Crew
7.8
Boarding
7.0
Comfort
7.1
Reviews
1 / 20
8.0
ExcellentMichael,Dec 2025
FNC - LIS
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.
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Alternative routes for Chicago to Madeira
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Madeira by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Madeira by cabin class
Find flights from Chicago to Madeira, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Madeira flights
Browse other Chicago and Madeira flight options. Last updated on April 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$548 | Average$877 | FlexibilityNo cancel fee | On-timeN/A |