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 Celebrating His Lack of Skill 04:05 The News of a Lifetime 03:03 The World's Oldest Profession 03:42 It Begins With a Simple Step 02:20 Red Light District Tour 02:45 The Funny Side of Sam Brown 01:24 Portland's Urban Bike Loop 02:19 Animal Myth Busted: Diamondback Rattlesnake 02:11 Shane O Visits Ballard Locks 02:53 Tiny Bear Cubs 01:09 Atlanta's Must-See Spots 03:03 Play With a Real Bulldozer 02:45 We Recommend Disappearing Places 16 Photos The World's Best River Cruises 11 Photos Top 10 Natural Wonders 10 Photos Waterfall Wonders 16 Photos Seven Wonders of Winter 7 Photos How to Ski Crowd-Free in Colorado 10 Photos