The Pedway will come in especially handy especially during winter, when the wind and the chill can make walking the Loop above ground a feat for the brave, or the numb. This network of tunnels covers about 40 city blocks and connects several hotels, like Swissotel and the Fairmont, to skyscrapers, stores and train stops. Artist Hui-Min Tsen is known for leading free Pedway tours; the 2-mile trudge takes 90 minutes.
Ride the River, Skip the Cab
For a unique vantage point of the city while getting from Point A to Point B, ride a water taxi along the Chicago River. This is a seasonal service, running a closed loop spring through autumn from Chinatown to Madison Avenue, but a special way to navigate the city and avoid street congestion. Chicago Water Taxi is operated by the famous Wendella Sightseeing Co., which, along with several other great boat and kayak companies, also provides wonderful architectural tours along the water.
See the Flatiron, Skip the Art Institute
The cultural weather at the Art Institute of Chicago is breathtaking. But the Flatiron Arts Building is a sight to behold, with 88,000 square feet of space in Wicker Park that allows artists and musicians to live in the very studios in which they create. This artists' colony, housed inside a building that is, itself, an architectural marvel, has been around since the 1980s. And artists regularly welcome visitors, like painter Hiromi Tanaka in Studio 205 and tile-maker Karen Gagich in Studio 339.
Watch from Hancock, Skip the Skydeck
There's no denying the drama that the views from the Willis Tower's Skydeck have to offer; you're on the 103rd floor of the world's third-tallest building, after all, and those glass boxes jet out more than 4 feet from the ledge. But you can avoid the crowds by checking out the sweeping visuals from the Observatory at the John Hancock Center across town; the 360-degree outlook from 1,000 feet up allows you to catch glimpses of four states and, every January through March, a 900-square-foot ice rink opens its doors.
Also at the Hancock: the Signature Room on the 95th floor, where you can catch the sights while sipping a stiff one. And speaking of views: consider the seven-minute ride on the Ferris Wheel at the Navy Pier, which sweeps you 150 feet above the ground over and over.