Chicago in 24 hours

  • Oli Chapman
On the shores of Lake Michigan in the heart of the Midwest States, lies Chicago, the ‘Windy City’.
As America’s third most populated city and as one of the most important business centres in the world, a rise in gentrification and urban regeneration over the past decade has seen Chicago become a diverse mixture of Manhattan and Shoreditch.
My aim? To see several layers of Chicago, recognise its history, culture and global notoriety, whilst trying to cram it into 24 hours. So, here are the must-sees in the Windy City.
The 606
The 606 is a former railway line, which in 2015 was opened as an elevated parkway and greenspace, that runs through some of Chicago’s most popular areas: Logan Square, Humboldt Park, Bucktown and Wicker Park.
A more suburban sister of New York’s famous ‘High Line’, the 606 is a perfect way to see some of the most vibrant areas of Chicago, while spotting great views of the Chicago Loop.
Wicker Park
As one of Chicago’s most popular areas, Wicker Park is a hub for clothes, records, bars and restaurants in Chicago. It’s an area that has received benefits from gentrification while maintaining its identity, creating a perfect mixture of new and old.
Make sure to check out Chicago’s exclusive Devil Dawgs, the Chicago chain that is home to some of the best hot dogs in the Midwest, give in to sin and indulge.
Garfield Park Conservtory
The Garfield Park Conservatory which was established in the last 19thcentury, is Chicago’s answer to a botanical garden and works as, “landscape art under glass”. With an extensive water lily garden (an ode to Claude Monet), desert and tropical plant collections, along with a 12-acre gardens that are open in the summer, the Garfield Park Conservatory is an excellent example of the diverse option of activities and sights to see in Chicago.
The Loop
The Chicago Loop refers to the main centre of the city and is the area that is most well-known. Predominant sites of the loop include the Willis Tower, which was formerly the tallest building in the world (1973-1998), Anish Kapoor’s Cloud Gate (also known as ‘The Bean’ because, well… it looks like a bean) and the Chicago Theatre, one of the most iconic theatres in the United States.
Pablo Picasso’s unnamed sculpture in Daley Plaza, which was given to Chicago as a gift from Picasso, is an icon of modern art located in the heart of the city and is worth seeking out; as is Alexander Calder’s Flamingo sculpture only 10 minutes away.
Navy Pier
Chicago’s number one tourist attraction is something to definitely see as it captures some of Chicago’s best elements along with some beautiful views. Sticking out into Lake Michigan and with views not only of the city but over to Indiana, Michigan and Wisconsin, the Pier is full of attractions, amusements, host to regular exhibitions and is constantly popular.
It’s the Midwest’s answer to Brighton Pier and Coney Island mashed into one!
More from Oli @chapman_oli


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