Travel + Leisure readers voted Chicago as the nation's “Best Skyline”. It is quite stunning if we do say so ourselves. And not to brag, but we look pretty good from every angle—up in the sky from one of our skyscrapers or down below from a river boat cruise or walking tour. Everywhere you look there’s a treasure trove of architectural wonders like The Wrigley Building, the Cadillac-Palace Theater and The Jeweler’s Building.
For a bird’s eye view of the city at 1,300 feet, step out onto The Ledge, a suspended glass box from the Willis Tower, at Skydeck Chicago. Or zoom up 1,000 feet for a 360-degree view of four states from the John Hancock Observatory—voted Chicago’s best view by TripAdvisor and the Chicago Tribune.
You can also take in the sites while sipping on a cocktail. Views from The Signature Room on the 95th floor of the John Hancock Center and Sixteen at Trump International Hotel & Tower are impressive.
There are many ways to see Chicago. Find a tour that meets your style. Here are a few to get you started. Walk the city with Chicago Detours, Chicago Savvy Tours, Joyce Walks Chicago and the Chicago Architecture Foundation, which is also known for its bus and boat tours. Or look through your lens with Chicago Photo Safaris teaching you how to capture terrific shots while seeing the city.
Or get a zoom with a view on a Segway sightseeing tour by Absolutely Segway, City Segway Tours, Segway Experience of Chicago and Steve's Segway Tours. Biking tours will also cover a lot of ground. Consider Bike and Roll and Bobby’s Bike Hike.
For those who like to explore on their own, consider a Metrowalkz Self-Guided Walking Tour or the Chicago Trolley & Double Decker Co. Hop On Hop Off Tour that covers miles of city attractions.
The Wright Stuff
No other place in the world has better examples of Frank Lloyd Wright’s Prairie style designs than Chicagoland. Visit the Frank Lloyd Wright Home and Studio in nearby Oak Park. Daily tours allow you to explore Wright's home and studio as well as the Historic District where they’re located.
Then when you are in the city, head to the University of Chicago’s campus in the beautiful Hyde Park neighborhood to see Frank Lloyd Wright’s Robie House, considered one of the most important buildings in American architecture.
Then see the Glessner House, a national historic landmark in Chicago’s South Loop, where a young Wright got his inspiration. The Glessner House was designed by American architect Henry Hobson Richardson and was a radical departure from the traditional Victorian architecture of its era.