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Traveling Across America Days 7 and 8: The Windy City is…Really Windy

by Wesley Banks | Follow Him on Instagram Here

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Day 7 Quick Stats

The plan: Check out our full road trip plan here

Starting point: Milwaukee, Wisconsin
Ending point: Chicago, Illinois

Miles driven: 92 miles
Hours traveled : 11:00 a.m. to 2:45 p.m.

Miles walked: 19 miles
Hours traveled : 10:10 a.m. to 5:40 p.m.

Cool things along the way: Miller Park, Millennium Park, “The Bean,” Navy Pier, Giordano’s stuffed pizza, Michigan Ave., Lincoln Park Zoo, chocolate cupcake at Molly’s Cupcakes, chili cheese dog at Portillo’s, chocolate cake doughnut at Firecakes, Skydeck at Willis Tower, Chicago Skyline at sunrise, Soldier Field, United Center

One more stop before Chitown

After sleeping in a bit, we got up and headed to Miller Park on our way out of Milwaukee, where Story and I paid homage to Hank Aaron and Robin Yount.

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I’ve never seen so much traffic

I’ve worked in Miami and Seattle, and I’ve traveled through Los Angeles, San Francisco, and New York City. Yet, I’ve never seen a more congested and crazy area than downtown Chicago.

Stopping by a few famous places

By the time we got checked in and unpacked it was already late afternoon, but we made the most of it by walking to Millennium Park to see “The Bean.” (Note: that’s us waving in the pink and black jackets)

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We then headed north to the Navy Pier. Unfortunately most of the pier was closed off for construction, but we got to taste some of Chicago’s famous deep dish pizza at Giordano’s.

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We finished out the night with a stroll down Michigan Ave. (aka “The Magnificent Mile”), which was full of bright lights and endless people.

Hiking through The Windy City

I apologize to anyone who takes offense to this, but I very much do not understand how anyone could enjoy living in Chicago.

It’s not even winter, and yet it was in the 30s most of the day with winds gusting near 40 mph on occasion. Not too mention the lovely buildings that literally blot any hope of the sun.

As bad as it was, I have to admit that Chicago is by far the most scenic and cleanest of the large cities I’ve been in (i.e. Los Angeles, San Francisco, New York City).

As high as the sky

We started the day on a 100+ floor elevator ride to the Skydeck at Willis Tower where we got pretty spectacular views of the entire city.

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The food was amazing

Up next was a quick trek to Portillo’s for a famous Chicago hot dog, which was by far the best chill cheese dog I’ve ever had.

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My wife was dead set on visiting Molly’s cupcakes (former Cupcakes Wars winner), so we set off an hour long walk down Clark St. Just thankful to get out of the cold at that point the cupcakes were a bonus.

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The zoo was sad

We were contemplating a cab ride back to the city – the weather was that miserable – but we opted to walk back instead.

We walked through the Lincoln Park Zoo, and watched bears and wolves pace back and forth sadly in their enclosures. I couldn’t bring myself to take any pictures. I know there are many good reasons for zoos, but after seeing so many wonderful animals in Yellowstone and Grand Teton it was just difficult to see them caged here.

We did however make our way through the rest of the park, which I imagine was even more incredible in early Autumn.

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More food…

After a couple more hours of walking it was time to refuel, so we grabbed some donuts at Firecakes.

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Another half hour or so down Clark St. and we were glad to be back in our hotel room, warm and dry.

Sunrise and stadiums

A trip to Chicago wouldn’t be complete without an attempt to see the skyline at sunrise or sunset. The sunset didn’t work out due to weather, but it was more than worth it waiting for the sunrise at The Adler Planetarium.

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Growing up a Bulls fan

Growing up as Bulls fan, who could resist a picture next to Michael Jordan at the United Center?

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Dear Chicago, I enjoyed my time in your city, but it is unlikely I will ever return.

Other posts in the Traveling America series:

  • Day 0: I’m Traveling Across America (And One Day You Should Too!)
  • Day 1: Discovering Snake River and Eating Chick-fil-a
  • Day 2: Someone Turned Down the Shoshone Falls
  • Day 3: Face to Face With a Grizzly Bear
  • Day 4: Rediscovering the True Wild and the Old West
  • Day 5: Bad Weather and Beautiful Colors
  • Day 6: Every City Needs Waterfalls
  • Days 7 and 8: The Windy City is…Really Windy
  • Day 10: The Most Beautiful Scenery and the Most Disgusting Hotel
  • Days 11 and 12: New York Countryside and Massachusetts Coast
  • Day 13: New Haven and Old Friends
  • Day 14: The Land of the Free and Chocolatey
  • Day 15: Science, God, and Disappointment
  • Days 16, 17, and 18: The Blue Ridge Parkway (Still Amazing)

About Wesley Banks

Wesley Banks is an author, professional engineer, world traveler, and dog lover. His latest novel Faith In Every Footstep is now available. Be sure to check him out on Instagram.

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I’m a writer, engineer, world traveler, and dog lover. This blog is where I share the journey of my stories that eventually turn into books. To find out more about me, read my full bio or come chat with me on Instagram.

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