$379+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — FNC
Jun 28 — Jul 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Madeira with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 May 29, 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 May 29, 2026.
This Scandinavian Airlines deal was found by Cheapflights users on 5/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:15 pm
ORD
- FNC
2 stops37h 50m
Scandinavian Airlines
Tue 11/103:55 pm
FNC
- ORD
2 stops54h 50m
Scandinavian Airlines
Deal found 5/28![Scandinavian Airlines logo]()
$684
This Scandinavian Airlines deal was found by Cheapflights users on 5/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:15 pm
ORD
- FNC
2 stops37h 50m
Scandinavian Airlines
Sat 11/73:35 pm
FNC
- ORD
2 stops31h 10m
Scandinavian Airlines
Deal found 5/28![Scandinavian Airlines logo]()
$714
This Gotogate deal was found by Cheapflights users on 5/28. 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.
Wed 11/47:00 pm
ORD
- FNC
1 stop21h 55m
TAP AIR PORTUGAL
Tue 11/106:10 pm
FNC
- ORD
1 stop27h 20m
TAP AIR PORTUGAL
Deal found 5/28![TAP AIR PORTUGAL logo]()
$735
This Justfly.com deal was found by Cheapflights users on 5/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 pm
ORD
- FNC
1 stop19h 15m
TAP AIR PORTUGAL
Tue 11/104:10 am
FNC
- ORD
1 stop17h 20m
TAP AIR PORTUGAL
Deal found 5/28![TAP AIR PORTUGAL logo]()
$751
This oojo deal was found by Cheapflights users on 5/27. 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 8/196:00 pm
ORD
- FNC
1 stop11h 40m
TAP AIR PORTUGAL
Tue 8/259:55 pm
FNC
- ORD
1 stop22h 50m
TAP AIR PORTUGAL
Deal found 5/27![TAP AIR PORTUGAL logo]()
$755
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Wed 11/47:00 pm
ORD
- FNC
1 stop12h 30m
TAP AIR PORTUGAL
Sun 11/87:50 am
FNC
- ORD
1 stop13h 40m
TAP AIR PORTUGAL
Deal found 5/28![TAP AIR PORTUGAL logo]()
$776
This Scandinavian Airlines deal was found by Cheapflights users on 5/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:15 pm
ORD
- FNC
2 stops61h 30m
Scandinavian Airlines
Tue 11/103:00 pm
FNC
- ORD
1 stop31h 45m
Scandinavian Airlines
Deal found 5/28![Scandinavian Airlines logo]()
$797
This Cheapflightsfares deal was found by Cheapflights users on 5/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 pm
ORD
- FNC
1 stop11h 40m
TAP AIR PORTUGAL
Wed 7/299:55 pm
FNC
- ORD
1 stop20h 45m
TAP AIR PORTUGAL
Deal found 5/28![TAP AIR PORTUGAL logo]()
$799
This Cheapflightsfares deal was found by Cheapflights users on 5/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 pm
ORD
- FNC
1 stop21h 05m
TAP AIR PORTUGAL
Fri 8/214:05 am
FNC
- ORD
1 stop17h 55m
TAP AIR PORTUGAL
Deal found 5/25![TAP AIR PORTUGAL logo]()
$818
This Scandinavian Airlines deal was found by Cheapflights users on 5/28. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:00 am
ORD
- FNC
2 stops25h 10m
Scandinavian Airlines
Tue 11/103:55 pm
FNC
- ORD
2 stops54h 50m
Scandinavian Airlines
Deal found 5/28![Scandinavian Airlines logo]()
$821
This British Airways deal was found by Cheapflights users on 5/28. 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.
Tue 11/35:10 pm
ORD
- FNC
1 stop15h 10m
British Airways
Thu 11/125:00 pm
FNC
- ORD
1 stop26h 50m
British Airways
Deal found 5/28![British Airways logo]()
$826
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 May 29, 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 May 29, 2026.
This British Airways deal was found by Cheapflights users on 5/27. 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.
Wed 11/185:10 pm
ORD
- FNC
1 stop17h 00m
British Airways
Thu 11/265:00 pm
FNC
- ORD
2 stops32h 20m
British Airways
Deal found 5/27![British Airways logo]()
$834
This KLM deal was found by Cheapflights users on 5/28. 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.
Thu 11/51:30 pm
ORD
- FNC
2 stops21h 40m
KLM
Wed 11/1110:25 am
FNC
- ORD
2 stops17h 09m
KLM
Deal found 5/28![KLM logo]()
$949
This TAP AIR PORTUGAL deal was found by Cheapflights users on 5/28. 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.
Wed 11/41:00 pm
ORD
- FNC
2 stops18h 30m
TAP AIR PORTUGAL
Thu 11/126:10 pm
FNC
- ORD
1 stop27h 20m
TAP AIR PORTUGAL
Deal found 5/28![TAP AIR PORTUGAL logo]()
$1,011
This Mytrip deal was found by Cheapflights users on 5/27. 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 8/197:25 pm
ORD
- FNC
3 stops24h 05m
Multiple Airlines
Tue 8/252:15 pm
FNC
- ORD
2 stops35h 37m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$1,036
This Iberia deal was found by Cheapflights users on 5/28. 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 11/146:00 pm
ORD
- FNC
1 stop13h 30m
Iberia
Wed 11/182:10 pm
FNC
- ORD
1 stop30h 45m
Iberia
Deal found 5/28![Iberia logo]()
$1,086
This Scandinavian Airlines deal was found by Cheapflights users on 5/24. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:00 am
ORD
- FNC
2 stops26h 35m
Scandinavian Airlines
Sat 11/283:35 pm
FNC
- ORD
2 stops31h 10m
Scandinavian Airlines
Deal found 5/24![Scandinavian Airlines logo]()
$1,092
This KLM deal was found by Cheapflights users on 5/26. 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 10/195:20 pm
ORD
- FNC
2 stops34h 15m
KLM
Fri 10/306:00 pm
FNC
- ORD
1 stop26h 25m
KLM
Deal found 5/26![KLM logo]()
$951
This KLM deal was found by Cheapflights users on 5/25. 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 7/65:57 pm
ORD
- FNC
2 stops33h 38m
KLM
Wed 7/2210:25 am
FNC
- ORD
2 stops18h 14m
KLM
Deal found 5/25![KLM logo]()
$987
This Mytrip deal was found by Cheapflights users on 5/28. 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.
Sat 7/187:25 pm
ORD
- FNC
2 stops23h 30m
Multiple Airlines
Sat 7/2510:00 pm
FNC
- ORD
3 stops28h 16m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,109
This Mytrip deal was found by Cheapflights users on 5/28. 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 6/239:50 am
ORD
- FNC
2 stops28h 25m
Multiple Airlines
Tue 7/147:35 pm
FNC
- ORD
2 stops30h 17m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,147
Last-minute flights from Chicago to MadeiraDiscover last-minute flight deals from Chicago to Madeira. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Madeira. Data last updated May 29, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/24. 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.
Sun 5/312:20 pm
ORD
- FNC
1 stop36h 50m
Multiple Airlines
Sat 6/67:00 pm
FNC
- ORD
1 stop23h 00m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,236
This Justfly.com deal was found by Cheapflights users on 5/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:20 pm
ORD
- FNC
1 stop36h 50m
Multiple Airlines
Sun 6/74:55 pm
FNC
- ORD
1 stop24h 05m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,245
This Cheapflightsfares deal was found by Cheapflights users on 5/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:39 pm
ORD
- FNC
2 stops26h 31m
TAP AIR PORTUGAL
Wed 6/179:55 pm
FNC
- ORD
1 stop20h 45m
TAP AIR PORTUGAL
Deal found 5/25![TAP AIR PORTUGAL logo]()
$1,009
This Mytrip deal was found by Cheapflights users on 5/28. 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 6/221:59 am
ORD
- FNC
3 stops36h 16m
Multiple Airlines
Tue 7/149:55 pm
FNC
- ORD
2 stops25h 02m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$1,128
This Kiwi.com deal was found by Cheapflights users on 5/26. 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.
Sun 6/289:00 pm
ORD
- FNC
1 stop22h 15m
Multiple Airlines
Mon 7/67:30 am
FNC
- ORD
2 stops36h 55m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$1,193
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Sun 6/289:00 pm
ORD
- FNC
1 stop22h 15m
Multiple Airlines
Sun 7/58:40 am
FNC
- ORD
2 stops35h 45m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$1,231
This KLM deal was found by Cheapflights users on 5/26. 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 6/294:50 pm
ORD
- FNC
1 stop34h 45m
KLM
Mon 7/610:00 am
FNC
- ORD
1 stop34h 15m
KLM
Deal found 5/26![KLM logo]()
$1,219
This Mytrip deal was found by Cheapflights users on 5/25. 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 6/2911:05 am
ORD
- FNC
3 stops26h 10m
Multiple Airlines
Sun 7/59:35 pm
FNC
- ORD
3 stops30h 30m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$1,259
This KLM deal was found by Cheapflights users on 5/26. 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 6/294:50 pm
ORD
- FNC
1 stop34h 45m
KLM
Sun 7/56:35 pm
FNC
- ORD
1 stop25h 55m
KLM
Deal found 5/26![KLM logo]()
$1,289
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 May 29, 2026.
Search for one-way flight options from Chicago to Madeira. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 7/2510:25 pm
ORD
- FNC
3 stops44h 50m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Wed 9/27:25 pm
ORD
- FNC
2 stops21h 40m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 7/187:25 pm
ORD
- FNC
2 stops23h 30m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$434
This Kiwi.com deal was found by Cheapflights users on 5/27. 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.
Sun 7/127:25 pm
ORD
- FNC
3 stops36h 40m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$461
This Expedia deal was found by Cheapflights users on 5/27. 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 7/154:55 pm
ORD
- FNC
1 stop13h 30m
Iberia
Deal found 5/27![Iberia logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 5/27. 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.
Thu 7/167:25 pm
ORD
- FNC
3 stops46h 15m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 7/119:57 pm
ORD
- FNC
3 stops55h 08m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$474
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 May 29, 2026.
Round-trip from | $684 (Scandinavian Airlines) |
|---|---|
One-way from | $379 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $1,095 |
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 29, 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
Wed 11/18
5:10 pm-4:10 pm
1 stop17h 00m
Funchal Madeira
Thu 11/26
5:00 pm-7:20 pm
2 stops32h 20m
$834
Quickest round-trip
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Thu 11/5
1:30 pm-5:10 pm
2 stops21h 40m
Funchal Madeira
Wed 11/11
10:25 am-9:34 pm
2 stops17h 09m
$949
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Mon 10/19
5:20 pm-9:35 am
2 stops34h 15m
Funchal Madeira
Fri 10/30
6:00 pm-3:25 pm
1 stop26h 25m
$951
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Mon 7/6
5:57 pm-9:35 am
2 stops33h 38m
Funchal Madeira
Wed 7/22
10:25 am-10:39 pm
2 stops18h 14m
$987
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Wed 11/4
1:00 pm-1:30 pm
2 stops18h 30m
Funchal Madeira
Thu 11/12
6:10 pm-3:30 pm
1 stop27h 20m
$1,011
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Wed 8/19
7:25 pm-1:30 am
3 stops24h 05m
Funchal Madeira
Tue 8/25
2:15 pm-7:52 pm
2 stops35h 37m
$1,036
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sat 11/14
6:00 pm-1:30 pm
1 stop13h 30m
Funchal Madeira
Wed 11/18
2:10 pm-2:55 pm
1 stop30h 45m
$1,086
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Fri 11/20
7:00 am-3:35 pm
2 stops26h 35m
Funchal Madeira
Sat 11/28
3:35 pm-4:45 pm
2 stops31h 10m
$1,092
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Sat 7/18
7:25 pm-12:55 am
2 stops23h 30m
Funchal Madeira
Sat 7/25
10:00 pm-8:16 pm
3 stops28h 16m
$1,109
ChicagoFunchal
ORD - FNC
ORDFNC
Chicago O'Hare Intl
Tue 6/23
9:50 am-8:15 pm
2 stops28h 25m
Funchal Madeira
Tue 7/14
7:35 pm-7:52 pm
2 stops30h 17m
$1,147
Showing 1-10 of 20 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, November is the cheapest month in which you can book a flight from Chicago to Madeira (average of $462). Flying from Chicago to Madeira in August is currently the most expensive (average of $704). 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 May 29, 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.
Entertainment
6.3
Food
6.2
Overall
7.2
Boarding
7.0
Comfort
7.1
Crew
7.8
Reviews
1 / 20
10.0
ExcellentMelanie,May 2026
ORD - LIS
Entertainment
6.3
Food
6.2
Overall
7.2
Boarding
7.0
Comfort
7.1
Crew
7.8
Reviews
1 / 20
10.0
ExcellentMelanie,May 2026
ORD - 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.
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 May 29, 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 May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$545 | Average$903 | FlexibilityNo cancel fee | On-timeN/A |