It’s a Friday night in Chicago and I’m sitting in a corner coffee shop, waiting for my Virgin Atlantic colleague to arrive for a 20 hour tour of the city. If I didn’t know better, I’d assume Chicago is called The Windy City because of this weather — a storm is heading our way. Through a large picture window, street lights are twinkling and attractive, collegiate young people crowd the busy sidewalk. As in most places that host an abundance of universities, there’s a natural buzz of excitement.
With its public bike sharing system, above ground L-train, parks, water access and above-average cleanliness, I’d rank Chicago among the top U.S. cities for quality of living. Locals warn me to hold judgement until after a winter visit — I’ll take that dare.

These are just a few things to check out:
- Sail on Lake Michigan during the Annual Air and Water Show
- Stroll among the unusual statues and landscape art in Millennium Park
- Wander into one of the traditional blues clubs for dancing and drinks
- Visit the John Hancock Observatory for a 360° view from 1000 ft. above Lake Michigan and Magnificent Mile
- Take Chicago River boat tour to see the unusual contrast of European-style architecture and sleek skyscrapers