vacation in chicago

Chicago: Six reasons to visit

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.

Little India

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.

Outdoor pursuits

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.

Retail therapy

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.

Sail away

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.

Plan your Chicago holiday

Words by Maureen Mclafferty, British Airways’ Chicago airport manager

Photography by Sawyer Bengtson on Unsplash

Dear Diary,

I’m enjoying my vacation more than I thought I would. Sam is running L-Corp beautifully, based on the lack of news I’ve seen; James is still doing fantastic work over at CatCo, and Kara is, well, to be honest, she’s the only thing I’ve thought about for the past three days. She’s just so… beautiful? And strong? She kinda reminds me of Supergirl, but they’re also really different.

Don’t get me wrong, Supergirl is amazing, and super (ha!) hot, but there’s something about Kara’s soft smile and her endless belief in me. She’s something else.

Anyways, I’ve been having a fantastic time in the Keyes! I got to swim with some dolphins yesterday. As soon as the people read the name on the reservation, they suddenly became very interested in making sure I had the best experience possible. I could start using a fake name, but as long as I can’t hear what they’re saying behind my back, the treatment isn’t bad. 

Since I’ve still officially left both of my companies, there really isn’t a point in me returning any time soon! I think I’ll go to Chicago next, I hear their beaches are really nice.