CHICAGO

The Windy City

Chicago

Chicago description


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Chicago 2022 Day 1

Day 1 of our Chicago trip from December 2022!

Chicago 2022 Day 2

Our first full day in Chicago! We head into Macy’s for a little bit of shopping, and then make our way north for an amazing dinner at Marge’s followed by a great evening enjoying the lights at the Lincoln Park Zoo!

Chicago 2022 Day 3

We spend our day at Navy Pier!

Chicago 2022 Day 4

We drive home from Chicago, I talk about the fascinating town of Pullman, and then Jess and I reminisce about our time in Chicago!

Chicago 2014 Day 1

Chicago is one of America's greatest and most historical cities, and there's nothing like a great city right before the holidays!

Chicago 2019

Jessica and I take a last minute trip up to Chicago to meet two of our travel host idols - Rick Steves and Samantha Brown!

Chicago 2014 Day 2

On the second day of our trip to Chicago we were joined by Jessica’s parents and younger brother, Michael.

Chicago 2016

Jessica and I explore Chicago for a few days! We try a few amazing restaurants, including The Boarding House, Xoco, and Bistro Campagne. We also explore the Museum of Science and Industry, and Bloomingdales.



Tyler’s Tips

Where to Eat & Drink

Where to stay

Top Sights and Attractions

Outdoor Recreation


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Chicago Script

Transcribed script from the Chicago videos.