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Chicago

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Big-shouldered, lakefront and delicious

How to get to Chicago → Plan 48 hours →

DestinationsUSA › Chicago

Architecture, deep-dish and a gorgeous lakefront — Chicago is a quick nonstop from Pearson and one of America's most walkable big cities.

Getting there

How to reach Chicago

Fly nonstop from Toronto Pearson in about 1h30. It's an easy long-weekend city.

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Getting around

Once you're there

The 'L' trains and buses cover the city; the Loop and Magnificent Mile are walkable; and the lakefront trail is made for cycling.

Don't miss

The best of Chicago

Millennium Park & Cloud Gate

'The Bean' and the city's front-yard park.

The Art Institute

One of the great museums, right downtown.

Architecture river cruise

The best way to read the skyline.

Deep-dish & the West Loop

Chicago's famous pizza and its buzzing food scene.

Chicago in pictures

Chicago

Chicago
Chicago
When to go

Timing your trip

Late spring through autumn is festival season; winters are cold and famously windy.

Do it on a budget

Smart-money tips

  • A CTA day pass beats single fares.
  • Millennium Park and the lakefront are free.
  • Look for free-admission days at the museums.

Ready for Chicago?

Compare the ways to get there, then build a day-by-day plan.

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FAQ

Chicago — common questions

How do I get to Chicago?

Fly nonstop from Toronto Pearson in about 1h30. It's an easy long-weekend city.

How do I get around Chicago?

The 'L' trains and buses cover the city; the Loop and Magnificent Mile are walkable; and the lakefront trail is made for cycling.

When is the best time to visit Chicago?

Late spring through autumn is festival season; winters are cold and famously windy.