Toronto to Chicago Flight Deals

The blues, deep-dish pizza, the Bears, Bulls, Cubs, Sox and Blackhawks; Hey, there's even an awesome city beach! Amazing public art, river architecture tours and rocking Grant Park summer music festivals are all signs you're in one of America's true great cities, the culture-rich melting pot, Chicago.

So cool it's a Broadway musical, Chicago is the hub of the Midwest and America's third largest city. On the shores of Lake Michigan, it is comprised of many neighbourhoods, almost all of which with massive parkland and an unmistakable flavour of their own. The downtown core is packed with landmarks and attractions that could easily fill a week's worth of touring so it's best to come with a plan.

The Windy City's towering skyline (including USA's tallest building in the Willis, formerly Sears Tower) is your first impression, a great introduction and its design and architecture is some of America's most dynamic and important. For an interesting perspective, hop on a guided river cruise tour to fully appreciate the various architecture styles, including early works of Frank Lloyd Wright and brilliant city planner Daniel Burnham.

With a gigantic Ferris wheel, an IMAX theatre, beer garden and a plethora of shops and restaurants, Navy Pier is Chicago's most visited attraction. Nearby, art-filled Millennium Park and the Frank Gehry silver-mirrored shell sculpture, represents the overall whimsical artistry of the city and its accessibility to the public. From the park, take a stroll on the pedestrian-only Nichols Bridgeway to the second largest art museum in the country, the world-class Art Institute of Chicago.

Hungry? Well, you're in the right place as Chicago loves to eat and the food scene here is some of the hottest in the country. Shaped by generations of worldwide immigrants, the city's food-loving culture makes it easy to find an authentic anything and everything, including of course, its own delicious signature bites like Chicago-style hot dogs and pizza.

The Second City comedy troupe got its start here and still performs today. Soulful South Side jazz and historic blues clubs pay tribute to the greats, many of which made their name here too. Art crawl or shop till you drop, Chicago is the quintessential American metropolis that should be tops on everyone's list of great American cities to see.

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Toronto to Chicago Depart: September 24, 2020
Return: October 1, 2020
$134 base + $86 taxes/fees