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A Walking (And Boating And Hopping) Tour Of Downtown Chicago.

Well, I hate to break it to you, but it seems as though I’ve fallen into that trap that people who are moving tell you they’ll never fall into but inevitably always do — that trap where I find myself sucked into the internet for eleventy-seven hours a day perusing sites like Zillow and Trulia and and virtually walking Google Maps streets and oohing and aahhing or cringing and shuddering at the possible neighborhoods where we might one day be living, even though I know — I know — I shouldn’t even peek until we have a contract on our house here.

My time should be spent marketing and networking and sprucing and selling — not flirting with a future that’s shaky at best.

But it’s so hard, you know, when you’re ready for change and the Present keeps insisting that you just. be. here.


In a crafty attempt to divert my brain (I’ll show you, brain), we’re going to take a quick peek back into the not-so-distant past. A past that, when it was the future, seemed chaotic and impossible. When the plan was to drive from North Carolina to Miami, pack up my sister’s belongings, and drive back to North Carolina. There, my sister would dog-sit for a week while Justin and I flew to San Francisco, drive to Oregon, and fly back home, at which point my sister and I would caravan to Chicago and move her things into her new apartment, spend a few days hanging out, and I would drive home and pass out for a week from sheer exhaustion.

And things pretty much went according to plan, except for one thing I didn’t anticipate.

I didn’t anticipate falling in love.


It happened.

I didn’t expect it, but I fell head-over-heels in love with the city of Chicago.


Here was my description the first time around, in case you missed it:

Friends, meet Chicago.

She’s an impeccably dressed city of approximately 2.7 million people, making her the third most populous city in the United States behind — you guessed it — New York and L.A. She’s 180-years-old, but let me tell you — she looks good for her age. Fresh and vibrant, she exudes none of that yellow L.A. smog or scent of N.Y. urine, and she probably has one hell of a plastic surgeon because visually, from every angle and even up close, she’s really quite stunning. Of course — my sister and I didn’t go trouncing around the South Side, mind you, where I’m sure we might’ve gotten a glimpse of some pimples or wrinkles or maybe a Ruger 9mm semiautomatic, but we weren’t about to go looking for these things.

As you can tell, she’s pretty special. And while I only had a couple of very short days to explore her treasures, I managed to put together a simple (and certainly not all-inclusive) list of obvious things you should see and/or do if you have a chance to visit this spectacular city:

EXPERIENCE A Culinary Tour.

Like I’ve said before, I firmly believe that a well-executed foodie tour is one of the absolute best ways to discover a new city. I already wrote about our culinary adventure of choice through Chicago’s China Town, and it’s an experience I’ll never forget.

Steamed barbecue pork buns.
Steamed barbecue pork buns.

EXPLORE Old and New China Town.

Chicago’s China Town was such a cool thing to see. We explored much of it during our food tour, and I know I’ll go back next time for more.


Old China Town.

New Chinatown

New China Town

RIDE the Water Taxi.


It turned out that our visit to China Town, which is located near the southern part of Chicago, was a perfect launching point for exploring the rest of the city because it’s the last stop for the water taxi! The taxi stop is inside Ping Tom Memorial Park, which is a beautiful place to explore while you wait with a spectacular view of the city skyline.


View from Ping Tom Memorial Park.


Umm… Chinese checkers?


What? Just burning off some dim sum.


We certainly know how to kill time.

I was told by many that I should take the architectural river tour of Chicago, but since that wasn’t in the budget this time around, I found taking the water taxi ($7 for an all-day pass) was the next best alternative. We parked for the day in a lot near China Town ($14 for the day?), and used the water taxi after our tour to head into the heart of the city.


On a nice day, grab a seat in the front of the taxi for some amazing city views.


Did I mention this city is beautiful?


WALK Michigan Avenue.

Look. They don’t call it “The Magnificent Mile” for nothin’. That’s the northern part of Michigan Ave., where high-end boutiques and eateries abound.


But you can’t neglect the southern end of this street, which runs along Grant Park, in front of the Art Institute of Chicago, and up to Millennium Park.


VISIT Millennium Park.


Just do it.

GAZE at the Bean.






…and feel sorry for the person responsible for keeping it clean.

TRAVERSE the Art Institute Bridge.

From there, you get great views of the city and a peek at Lake Michigan.


CONSUME Chicago Style Pizza.

I will just say this. I had no idea what “Chicago Style” pizza was before I went to Chicago.

No idea.

But then we got this pizza — no, pie — no, pizza — with a crust, at least an inch of filling, another crust, and some sauce.


And like… it was so incredibly good that we were able to forgive the restaurant for forgetting all of our meat.


This pizza was supposed to be filled with sausagey goodness. Fail. But still delicious.

I still crave these to this day.

DRINK Chicago Beer. Or Just Drink.

Stopping for a beverage on Michigan Avenue was a great way to rest our weary feet.


This is Irish beer. Not Chicago beer. Pronounced “Smiddick’s,” it’s one of my fave’s.

So that was our whirlwind tour of Chicago. This list, like I said, is not all-inclusive. I’m sure I missed a lot. Like Navy Pier and The Loop at night and actual meat in my pizza.

But that really only means one thing.


It means I have to go again.


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LiLi Sheree

Looooooove this! I am planning a trip in October with my friend. Hopefully it won’t be too cold and I can get out and see the sights that I have yet to see in past visits. This showed me all I’ve been missing out on!


So fun!! Dress warm so you can take the water taxi – it’s such a great city to just walk around and explore! :)


Chicago looks awesome and it looks like you had a great time :-) Thanks for sharing all the gorgeous buildings and beautiful sights – I definitely want to visit someday!


We did, and you should! I seriously think I could live in that city. I just need a lot more money and for it to move a latitude line or two further south. ;)

Colleen Brynn

Seriously, how great is Chicago! Every time I’m there, I’m just so pleased.
I love the beer and pizza… soooo good.


“Pleased” is such a great way to describe how I felt when I was there. Just… happy. That city has such a great vibe!


What a great city!! I could live there from April – September but when winter hits, I’d have to head to Bangkok. Great pics!


Exactly. I’m not sure I could handle their winters! But for the vibe of the place, I’d probably be willing to give it a shot.

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