The Windy City is often overshadowed by its coastal counterparts, but with steely skyscrapers, culturally diverse neighbourhoods and the great outdoors nearby, it’s time to take another look at America’s second city.
The Italian job
Photo by Thomas Schweighofer on Unsplash
About 30 minutes west of downtown Chicago you’ll find Il Poveretto Café. The Melrose Park neighbourhood is known for Italian restaurants and this is a favourite. The owner, Frankie, treats everyone like family. The Italian village salad is the perfect starter, but save space for spumoni cheesecake.
Strolling down Devon Avenue, you’d be forgiven for thinking you’re in India. Most come to dine, as there are plenty of superb Indian restaurants, including Annapurna, but don’t miss popping into the many sari shops - the colours are breathtaking.
Chicago is home to the 30km lakefront trail, a beautiful park space separating downtown Chicago from Lake Michigan. Dotted along the lakefront are 26 natural sand beaches where you can rent paddleboards, jet skis, and kayaks, or kick back with a nice cocktail at a beachside café. If biking’s more your thing, head out onto the city’s 320km of designated bicycle lanes – Chicago was recently named the most cycling-friendly city in America.
Tread the boards
Take a tour of the historic Chicago Theatre. Opened in 1921, it’s one of Chicago’s most iconic buildings, and the backstage wall is filled with autographs from showbusiness stars, including Frank Sinatra, Dean Martin and Dolly Parton.
Get your shopping fix on State Street, that great street, as the song goes, home to Macy’s, the second largest department store in the world. Then hop over the Chicago River to The Magnificent Mile. There you can enjoy jaw-dropping city skyline sights and be spoiled for choice with its 460 shops.
No trip to Chicago is complete without hopping on the Chicago Architecture Foundation River Cruise. It’s amazing - you’ll learn why the city’s buildings are built the way they are and why the river flows backwards, plus you’ll get the lowdown on the newest skyscrapers.