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#YouDoNew - Chicago

I'm apparently on a travel kick lately, and I'm totally alright with that.

I love to go to new places and experience new things, but prior to last month's adventures in Collingwood (recounted in two parts) I hadn't left the area in almost two years. So now I'm making up for lost time as quickly as possible, apparently. I had previously driven through/around Chicago as a kid going on vacation with my parents, and again a few years ago when I drove out to Banff, but had never actually spent any time there. I still hardly have I guess, but I'm getting ahead of myself.

So a couple weeks back my boyfriend's grandma tells me how she has to go to Chicago for some paperwork signing, because that's how the world works, and that Phil would be taking her as the drive was a bit much to do on her own. She asked if I would come so he wouldn't have to do all that driving on his own. They're set to go during my days off, and I like going places, so of course I'm all in.

It's about 5.5 hours to downtown Chicago from their home in Mount Clemens, so we leave really early in the morning - 5 a.m. or some other hour that I haven't been awake for in years.

We're taking Phil's Jeep Liberty, so I settle down on the folded-down seats in the back to get a little more sleep while we drive.

I end up passed right out before we make it to the highway and don't wake up again until Gary, Indiana.

Being the awesome Grandma that she is, there was a cooler of caffeinated drinks and non-caffeinated sandwiches in the back with me, so I spent the remaining hour of our drive doing my makeup and enjoying some eats that I didn't have to make myself (which means they were of course fantastic).

As we're driving into the city via the Skyway I'm getting an awesome view of the city and lake, and am thoroughly enjoying checking out the neat-looking sports stadiums and buildings we pass on the way.

We get downtown and find parking with very little trouble, and also get to take a quick peek at some wild old cars parked in the same garage.

Then Phil and I accompany his grandma to her appointment in the John Hancock Building, make arrangements to meet her when she's done, and head out to find something to do. We start with a quick wander around the Water Tower Place mall where we get more caffeine and spend some time in a neat Dr Seuss art gallery.

We've got a limited amount of time to do something - it's about 10:30 a.m. at this point, Grandma's appointment is at 11, and we're not expecting it to take long.

We discuss our options, and I'm really into the idea of checking out the observation deck at The John Hancock Building, known as Chicago 360. I figure it'll be just the right amount of time, we're in the same building as her, and if I've got enough time to do one thing in a city I'm visiting for the first time, what better thing to do than take a look at all of it in one go? Luckily 10:30 on a Wednesday isn't a busy time for this attraction, and there's no line whatsoever to wait in. Score. Less than ten minutes after making the decision to go we're on the 94th floor of a hundred-floor skyscraper, gazing out over Lake Michigan. And it's a hell of a view. Each wall of the large square room is solid windows, offering a complete view of the city. We were lucky enough for it to be a sunny and clear day, so visibility was great and I was certainly getting my wish of seeing all of Chicago at a glance.

We marvelled at the rooftop pools, tried to look down people's shirts, and watched some rain fall far out over the lake. I snapped a few photos and then we got the call to go back downstairs.

We grabbed lunch at M Burger before trying to check out the navy pier, but ultimately decided against it as we were hoping to leave by 1:30 to beat traffic, and would have ended up paying $28 for thirty minutes of parking.

Instead, we take a drive along the shore to get a look at the water and the city's architecture before turning around and heading back to Michigan. During this quick jaunt along the lake I planned my next trip to the city, where I would take a train, stay at an Airbnb, ride the publicly-available bikes to get around, and visit places like the Museum of Contemporary Art, The Navy Pier, and The Museum of Science and Industry, all while finally trying some of that famous Chicago-style pizza.

The ride home was fairly uneventful. I let Phil drive us out of the city, and then took over the rest of the trip from there. He was less of a backseat driver than I expected, and mostly worked on his laptop. Grandma sat in the front and napped, and I enjoyed my audio book (right now I'm on the last part of Ken Follett's Century Trilogy, and it's awesome).

By the time we got home we had been gone for about fifteen hours, with the majority of that time being spent in the car. It was a long day and a huge tease. I can't wait to visit Chicago again, and to hopefully see more of it from ground-level.

So to rate this week's new activities:

Chicago: 9/10 - seems like an awesome place, but the parking and driving situations aren't ideal. Welcome to large cities, I suppose. Chicago in 2 hours: 5/10 - not awful, if you find the right thing(s) to do, but definitely leaves you wanting more.

Chicago 360: 9/10 - fairly priced admission, probably a lot less fun when the lines are huge.

Driving 11 hours round-trip for a 3 hour stop: 2/10 - not so bad when you can sleep for most of it, but also not the best way to visit places, especially places you haven't been to before.

#YouDoNew - Week 9 - September 4 to 10

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