Chicago by Air, Land & Sea

  Flying overhead, rattling the windows of the John Hancock Observatory, parachuting to the ground and splashing through the water!  Chicago’s most exciting event, the Air & Water Show is just around the corner!  Will you be one of the almost 2 million people crowding the city’s lakefront to try and catch a glimpse of some of the best military and civilian pilots in the U.S.?  If watching high fliers like the U.S. Air Force Thunderbirds and U.S. Navy Parachute Team Leap Frogs inspires you to see Chicago from a different angle, we’ve got some suggestions.  Here are our favorite ways to see Chicago by Air, Land and Sea!


   You’ll be at the top of Chicago…literally, when you step onto the Ledge at the Willis Tower Skydeck!  The eighth tallest building in the world puts you more than 1,300 feet above the city!  And if you’re really daring, step out onto the glass bottom balcony to see Chicago from a whole new perspective!

If you want to get really high above Chicago, check out Chicago Aerial Tours and you can soar above the lakefront and skyline in a private airplane or helicopter tour.  We recommend the breathtaking night tour to see Chicago a glow in the evening!


If you would rather keep your feet on the ground, we don’t blame you.  Chicago was named as one of the most walkable cities in the country.  There are endless tours that can be customized to your own personal tastes and preferences.  Our favorite walking tour is the Chicago Greeter program…and happens to be free!  There are more than 200 enthusiastic guides ready to share their passion and  knowledge with you.  

Perhaps you’d rather zoom through downtown Chicago on two wheels?  Sure there are plenty of bike rentals available.  But how often can you rent a segway?  These two wheelers will help you glide past some of Chicago’s top attractions.  Two of the more popular segway outfitters are Absolutely Chicago Segway  and City Segway Tours.


Chicago sits on the shores of beautiful Lake Michigan and all summer long visitors can watch the many sailboats dotting the coast.  But you don’t have to be a boat owner to get out on the water.  Enjoy a ride on Windy, a traditional Tall Ship!  Daily sailing adventures leave from Navy Pier and make for a great family excursion. 

If you’re a do-it-yourself kind of traveler, who wants a great workout, you can rent a kayak from Kayak Chicago and paddle your way down the Chicago River!  You’ll be amazed when you enter into the ‘Canyon of Chicago’ as tall skyscrapers surround you on all sides.  Or enjoy an evening fireworks paddle to catch the twice weekly show from the cockpit of a kayak!


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