Trip Flip: Chicago Pictures

Bert surprises 2 friends with an all-expenses-paid dream adventure to the Windy City.

Filed under:
+ Enlarge Photo
Shrink Photo
Red Witch
Start Over

Gallery Link:

View All

A view of the Chicago skyline behind the Red Witch. Located on Navy Pier, the Red Witch is Chicago’s tallest -- and only -- wooden ship.

Loading...

Please forgive us, this gallery is really popular.

We sent a note to our support staff about the glitch you just experienced. Please click the button below to reload your content.

You May Also Like

Trip Flip: Grand Canyon Road Trip Pictures

Bert takes one lucky family on an all-expense-paid dream RV road trip to the Grand Canyon.

Trip Flip: Sydney Pictures

Two lucky vacationers prepare for an adventure Down Under with host Bert Kreischer. Their journey includes rappelling down waterfalls, hanging with koalas and kangaroos and much more.

Trip Flip: Puerto Rico Pictures

After agreeing to let Bert take the reigns and plan an amazing, all-expenses-paid trip to Puerto Rico, adventurers Chris and Whitney receive 2 tickets to paradise.

We Recommend

Most Popular

Puerto Rico Pictures

After agreeing to let Bert take the reigns and plan an amazing, ...

Costa Rica Pictures

Bert takes 1 lucky Idaho-based couple on an amazing tropical adventure ...

Swimming With Sharks Pictures

Bert takes 2 lucky vacationers on the adventure of a lifetime to ...

We'll Always Have Paris Photos

Bert takes newlyweds Craig and Heather Bacon to France for an ultimate ...

Florida Keys Pictures

Bert plans a 3-day adventure to the Florida Keys for 1 lucky couple ...

More Travel Inspirations

American Outdoor Adventure Sweeps
American Outdoor Adventure Sweeps

Enter for a chance to win an adventure getaway, plus $25k!

Food.com Holiday
Food.com's 50+ Top Holiday Food Gifts

Give them what they really want!

HGTV Dream Home
HGTV Dream Home 2015

Take a tour of the home we’ll be giving away. Look inside HGTV Dream Home 2015 now!