Pinterest Facebook Twitter Email Tailor-Made Guys Weekend 02:47 Bert surprises 2 California residents with an all-expenses-paid trip to Chicago. From: , Trip Flip and Chicago Similar Topics: Outdoors and Adventure Travel's Best Related Videos The Windy City Rollers 02:36 Chicago Nonstop Tour 04:09 Voracious Teenage T. Rex 01:25 A Monster of a Man 03:10 America's First Serial Killer 03:21 The Lady and the Panda 02:52 The Mother of CSI 03:14 On the Wings of X Flight 01:48 More Videos First Nuclear Test in History 02:29 Did a Cow Cause Chicago Fire? 02:51 Captured U-Boat Helps Win WWII 02:37 A Man Ahead of His Time 02:20 The News of a Lifetime 03:03 Celebrating His Lack of Skill 04:05 It Begins With a Simple Step 02:20 The World's Oldest Profession 03:42 Red Light District Tour 02:45 The Funny Side of Sam Brown 01:24 Play With a Real Bulldozer 02:45 Animal Myth Busted: Diamondback Rattlesnake 02:11 Josh Gates' Hometown 03:46 Prospect Park Pets in Brooklyn 01:43 Shane O Visits Ballard Locks 02:53 Bobsledding Water Slide 02:23 We Recommend Top US Off-Road Destinations 9 Photos Chicago’s Music Clubs Chicago Pictures 11 Photos Chicago Weekend Guide Trip Flip Enjoying Chicago's Parks