Once in a Lifetime: Chicago

By: Katie Manning

January 8, 2013

Beyond hot dogs and Millennium Park, we’ve found that Chicago has plenty to make a trip extra special. Whether you’re after an action-packed city break or simply some time away to unwind, these experiences have left us begging for more – and maybe even a change of home town”¦


Chicago | Alinea

Alinea, Chicago © Alinea

Ranked as one of the best restaurant in the world, chef Grant Achatz’s consistently wows us with his inventive creations in molecular gastronomy and multi-course tasting menus. Bite sized dishes are often suspended by wires above your table, food might come resting on an inflated pillow and each course basically comes with an instruction manual for how to eat it. This is food theatre like we’ve never experienced”¦ 1723 N. Halsted Street, Lincoln Park, Chicago, +1 312 867 0110,

Fork and the Road Culinary Bike Tours

Once in a Lifetime Chicago_Fork and the RoadFork and the Road © Lawkeeper/iStock/Thinkstock

There’s nothing we love more than the chance to stuff our faces while working it off. Cycling through Chicago sampling its eclectic ethnic restaurants (taquieras, Greek diners, Asian markets and more) is one of our favourite ways to see this city from an insider’s perspective and avoid the guilt a food-heavy holiday might otherwise inspire. You have to be at least 18 to participate and journeys range from 14 to 18 miles in length. Various starting points,

Bike the Drive

Chicago Once in a Lifetime_Bike the Drive.jpgBike the Drive Chicago © Seth Anderson/Flickr

For us, few things are cooler than joining thousands of bikers along 30 miles of Lake Shore Drive shut down to cars for five hours every Memorial Day weekend. It’s our idea of experiencing Chicago in a truly unique way. You get to enjoy the striking skyline and the shimmering water of Lake Michigan as you ride, but remember to sign up before hand and, oh, set your alarm clocks – the event begins at 5.30am”¦ Lake Shore Drive (starting point: Columbus Drive and Jackson Drive), Downtown, Chicago,

The Ledge at Skydeck Chicago in the Willis Tower

Chicago Once in a Lifetime_SkydeckSears Willis Tower, The Ledge © Jamie McCaffrey/Flickr

We guarantee you’ll lose your breath as you step off the 1,353-foot-tall Willis Tower into the glass-enclosed Ledge – a 4.3 foot outcrop you can walk out on and feel suspended in mid-air. We recommending getting your photo taken for a truly unique souvenir – it’ll really confuse friends back home”¦! It’s open 365 days a year but we suggest calling +1 312 875 9803 to set up an intimate catered breakfast before it opens to the public. 233 S. Wacker Drive, Downtown, Chicago, +1 877 759 3325,


Katie Manning

Katie is an author for the Virgin Atlantic blog. Despite her urban London residency, Katie can often be found exploring far-flung corners of the globe in search of exciting new experiences and stories. A self-confessed night-owl, she makes it her mission to search out the best cocktail bars and live music venues on each and every expedition. Follow Katie @kt_saramanning

Categories: Our Places