The Windy City: Part II

In Stories, Tales by Ariel0 Comments

Check out The Windy City Part I

I would like to start off by noting that Chicago is one of my favourite cities in the world – and my absolute favourite American city. I’ve been to quite a few major cities in the USA through my roadtrips: Las Vegas, Las Angeles, San Diego, San Francisco, Washington, DC., Orlando… but the best by far is Chicago (though I admit I’ve never been to New York… that might trump it). There’s something about this city that I just fell in love with the moment I entered… even though we were there in the middle of a heat wave (and we know how much I like hot weather)!

Maybe it’s the incredible architecture, maybe the picturesque location on the Lake, maybe it’s the melding of the old and the new, whatever it is, it makes Chicago great…



On our second day in Chicago we headed into the city centre and proceeded to try to find parking. Now I’m not saying that parking was hard to find or that there is a shortage of parking… but it’s expensive. I’d like to preface this by saying that it was expensive to our “small” city expectations – those of you in larger metropolitan areas might think nothing of paying $40-50 USD to park all day downtown. For us, it hurt. We eventually found parking by Macy’s which was $30 if you got your parking validated at the store – you didn’t have to buy anything, you just had to go in… because they knew you could never leave that store without going in…

I have to say I love Macy’s. My dad has no patience for shopping so on our previous road trip through the US we hadn’t stopped at a lot of stores… but this time he wasn’t with us and Chicago was our first major metropolitan stop on our trip and this was the first time I had ever gone to Macy’s.

What started our shopping problem was that I had to find a washroom… they were downstairs in a back corner by the housewares. While my mom and my brother were waiting for me they looked around and realized that Macy’s had some really nice stuff… and a really good sale happening. But we were travelling… we couldn’t possibly buy dishes in Chicago and drag them all the way down to Florida, right? Well, one of the perks about road trips (one that my oh, so clever brother was quick to point out) is that you have your own vehicle and no restrictions except space – and we were travelling with 3 people in a mini-van. Suffice it to say mom bought a whole new set of dishes, my friend’s wedding shower gifts and a few other odds and ends…

After the unwitting distraction that was Macy’s we headed down to the main street in downtown Chicago – Michigan Avenue, also known as The Magnificent Mile. This is where you find a lot of the magnificent architecture that makes Chicago stand out from the crowd. The older building such as the Tribune Tower and the Wrigley Building mixed in with the new skyscrapers like the Trump International Hotel and Tower. It makes for an absolutely stunning cityscape.






We spent a lot of our day simply wandering around, poking in shops. We visited the famous Bean, properly known as

Cloud Gate. There were a ton of people and it was hard to get a proper view or picture but it is definitely something you have to do if you’re in Chicago.


The one “touristy” thing we chose to do was take a boat tour of the river. Setting sail from just east of the DuSable Bridge at the crossing of Michigan Ave and East Upper Wacker Drive there are many options for your exploration of the city of Chicago by water. If there is one thing you do when visiting this city, I recommend getting in a boat and exploring it by water.


Starting point for your boat tour

We chose the partial architecture tour / partial Lake tour. This tour had just enough info on the spectacular architecture of Chicago plus it went out on Michigan Lake for an awesome view of the city. Once again, I recommend doing things near dusk – we got to view the city in the daylight but by the time we were coming in from the middle of the Lake the sun was setting and all the city lights were coming on. It was beautiful. After travelling onto the Lake we came back into the city proper and went up the river all the while being given interesting tidbits about the buildings around us (none of which I can remember to tell you…). It was just enough info for those of us not super interested in architecture to keep us engaged without being bored. My parents have since returned to Chicago and have taken the Architecture Tour which goes into much more detail for those interested. However, it does not go out onto the Lake but it does go farther up the river.


Leaving the Chicago River to enter Lake Michigan




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After that it was evening and we were exhausted from all the walking and sightseeing we’d done – the good kind of exhausted. I can’t even tell you what we ate or where else exactly we went but I know we had a marvelous time. So back we headed to our car and our hotel for our last night in Chicago.

The next morning we packed everything up and headed into the city once again. We’d decided we wanted to do one last “touristy” thing before we had to leave and decided on the Shedd Aquarium. This was relaxing, though quite busy as it was July 4th and a long weekend Monday. It was the perfect thing to do that morning/early afternoon before we had to leave the city and the State and head to Washington, DC!