Chicago, IL, USA to Madeira Island from $318: 3 ways by bus, train, flight or car

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Madeira Island with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company

various

Plane

Average Duration

12h  59m

Estimated price

$318-1211

Recommended

Select

Open full-size map

Distance: 6191 km

Duration: 12h 59m

See more options

Filters

Sort by

 

Company

Amtrak and various

Plane

Average Duration

17h  25m

Estimated price

$382-1047

Select

Company

various

Plane

Average Duration

13h  48m

Estimated price

$418-1111

Select

Browse car rentalsExplore flights

Traveling From Chicago to Madeira Island

You’ll find a striking contrast between the urban energy of Chicago and the tranquil landscapes of Madeira Island, where lush mountains meet the vibrant ocean.

Best Neighbourhoods in Madeira Island

Madeira Island boasts diverse neighborhoods, each offering distinct experiences for visitors.

Funchal

• Bustling capital with rich cultural attractions.

• Excellent dining options featuring local cuisine.

Câmara de Lobos

• Picturesque fishing village known for stunning landscapes.

• Famous for its vibrant poncha bars.

Machico

• Historic town with beautiful sandy beaches.

• Offers a charming blend of nature and heritage.

Best Times To Visit Madeira Island's Attractions

Planning your visit to Madeira's attractions can enhance your experience and avoid crowds.

Laurisilva Forest

Visit early mornings or weekdays to enjoy peaceful hikes and breathtaking views.

Pico do Arieiro

Late afternoon provides stunning sunset views with fewer tourists on the trails.

Funchal Market

Mornings on weekdays are less crowded, offering a more relaxed shopping experience.

Madeira Island Weather: What to Expect Year-Round

Madeira Island boasts a mild subtropical climate, making it a pleasant destination throughout the year. The best times to visit are from April to June and September to October, as these months offer comfortable temperatures and fewer tourists, enhancing your overall travel experience.

Dining Recommendation

For a true taste of Madeira, try the local dish 'espada com banana' at Restaurante O Polar, where succulent black scabbardfish pairs wonderfully with the sweetness of banana. Unlike Chicago's bustling dining scene, this restaurant offers a laid-back atmosphere with stunning island views, allowing you to savor bold flavors crafted from fresh, local ingredients.