Travel-blog: Chi-Town – August 5th – August 7th, 2015

Chicago Skyline from the Shedd Aquarium

On one of our first of many long walks together, my girlfriend, Nicole, mentioned that she makes a bucket list every summer. And after helping her check a few things off it late that summer, I decided that it was a pretty cool idea. So, come May 2015, I thought, hey, why don’t we make a bucket list together this year. She loved the idea. And I can now tell you making a summer bucket list a great way to make each summer worthwhile, make living in your home town much more interesting, or less boring, and create lasting memories that won’t blend in with all of the other everyday summer fun.

Although, there was a feeling of apprehension when I casually threw out the idea of a trip to Chicago during our bucket list brainstorm session. I had been to Chicago three times before: once for a baseball tournament, once for a hockey tournament, and once in 2014 for the music festival Lollapalooza. (Actually, I scored the tournament-winning goal during over time in the hockey tournament.) But, my jaw dropped when Nicole said, “I’ve never been there before.  We had to go.

The two of us tend to choose our purchases carefully, so the day we finalized the purchase was bitter sweet. A couple hundred bucks for train tickets and a hotel room left our bank accounts in the blink of an eye and a click of a mouse. But, as the adventure moved closer, our spirits rose, and when the day of our departure came we could hardly sleep. Just look at us on the AmTrak at 5:00 am…

Destination: Chicago, IL
Destination: Union Station, Chicago, IL

Yeah, we were those annoying people – too happy to be alive at dawn. And after six hours, a few stops, one time zone and some small talk with a family of Canadian Mennonites, we arrived at Union Station in Chicago, Illinois.  First stop, the Congress Plaza Hotel.

The Congress Hotel sits on Michigan Avenue, right outside of Grant Park, the location for Lollapalooza, only a short walk from what is known as the “magnificent mile.” The hotel was opened in 1893, and, for downtown Chicago, a stay-in is pretty reasonably priced – our room was only $160/night. No, it’s not a five star hotel, but, if you’re ballin’ on a budget, it’s an affordable way to stay in downtown Chicago. The architecture and interior design is beautiful. To see pictures and take a video tour, click here. Also, it was also only a couple of blocks away from Union Station, so we didn’t have to cab-it after getting off the train.

We caught our breath after checking in to our room, then headed south, to the Shedd Aquarium. As we moved through the park, listening to city buses accelerate and cars honk, observing all of the skyscrapers on Michigan Avenue, and catching glances of the boats in Monroe Harbor, it felt surreal to finally be in the place that, only a few months before, was a simple idea.

After our visit to Shedd Aquarium, we walked north next to the harbor. While playing chicken with a few geese, we gazed out at the blue waters and openness of Lake Michigan. Sail boats lining the harbor followed the water’s subtle movement up and down, held in place by anchors tied to floating buoys. At this location, surrounded by the green trees of the park, the cool harbor water of Lake Michigan, and the soft summer breeze, even the city air smelled fresh.

Heading to our next attraction, Skydeck Chicago, we stopped for a quick photo-op at the Buckingham Fountain on the north side of Grant Park, not too far from our hotel. We kept our pace up with the rest of the city-folk, moving quickly across the cross-walks and dodging the cars fighting for space in traffic. Entering Willis Tower on Jackson Boulevard, we took the elevator to the first Skydeck line. Using our CityPASS, we jumped the line to the next elevator, packing ourselves into the small cavity like sardines. Thirteen hundred feet, and 103 floors up, we had arrived at The Ledge of the Skydeck – the tallest building in the western hemisphere.

We approached one of the glass boxes that jutted out over the city. Gravity pulled at us. Nicole looked at me, “Let’s just get this over with…” I smiled and chuckled, trying to reassure her that it was completely safe. But, as she tried to make friends with the lady next to us, her male friend told the two of us a story about the glass supposedly cracking when a group of men stepped out onto The Ledge.

I yelled at him lightly. “C’mon, man, you’re gonna make her back out of it!”

It was our turn. I put my hand on Nicole as we stepped out. She looked right down, and reached for something to hold onto.

Oh my God!” Nicole cried.

Saying that you could see for miles was an understatement; the view was mesmerizing. The feeling in my stomach reminded me of being half way down the first drop of a roller coaster, and a sensation similar to vertigo made me want to sit down. I looked over to check on Nicole, and she said, “Okay, let’s take the picture!”

The view was so incredible I actually talked Nicole into taking a few more pictures.


But enough of the site-seeing. Let’s Eat!

We had worked up quite an appetite over the course of the day. Other than snacking on the train, we hadn’t eaten since 4:00 am. I’ll never forget the look on Nicole’s mom’s face when she came down to let the dogs out, and saw me making eggs and bacon. “Seriously?” 

I just smiled and said, “Gooood morning!”

We stood outside the Willis Tower as I searched on my phone to find a place to eat. Strangely enough, a haggardly man with yellow, “summer teeth” came up to us, rambling that his wife was having a baby right now in the nursing home… Nicole tightened her grip on my arm as the man cam a little close for comfort. He was talking so fast I could barely make out what he was saying.

“I’m three dollars short on my debit card to cover the bill. Can I borrow yours? Can you help me out?”

I wish I could have helped the man out – only three dollars and my debit card wasn’t going to do it. If that was all he needed, I think the nursing home would have let it slide. “I’m sorry, man, I can’t help you,” I said.

The man gave me a hard look and stormed away. Two blocks later, we saw him cornering a man using a similar story. I hope someone knows how to help him.

We ate an Irish pub called Poag Mahone’s. The beer and food were excellent – all of their beef was 100% grass fed, too. Great service, great place. If you’re around The Loop, or at Willis Tower, hit up Poag Mahone’s on Wells St. for a burger and beer.

100% grass-fed
100% grass-fed

We passed the Chicago Stock Exchange and the Chicago Public Library on our walk back to the hotel – both are absolutely massive. I tried being romantic. Nicole shook her head at me – she does that often.

What a day…

Day 1 over.
Day 1 over.


The next morning, August 6th at 7:00 am, I woke up to the song “What I Got,” by Sublime. Nicole and I popped right out of bed. After a quick shower, we threw a few essentials into the backpack, and we were out the door by 8:00 am. Two couldn’t ask for a better morning to begin a day long trek. The sun was shining bright during the morning buzz, and we headed north on Michigan Ave. First and foremost, we need a little fuel, so we stopped at….

Highly recommended for breakfast.
Highly recommended for breakfast.

My Lollapalooza crew and I ate here every morning on our 2014 adventure. It’s that good.

After a light breakfast, and copious amounts of coffee, we continued north down the magnificent mile, in awe of the humbling skyscrapers. You just have to see this stretch of the city for yourself. This is where companies like Apple, Burberry, Chanel, Disney and Nike all own big-time real estate. However, these images from Creative Commons will give you a snapshot of  what you will see on a walk down Michigan Avenue:

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We continued on admiring Chicago, observing the buildings and listening to the hum of the city, feeling its humbling size. About six miles from where we began our journey, we came to a place I had longed to visit since I was a boy – the historical town of…


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This historical field has a captivating presence. I wish we would have been there on a game day, because there is an aliveness about Wrigley. I have to imagine it would be like College Game Day. So, if you were a ball player, or simply love the game, you have to make it to Wrigleyville. It will give you a new appreciation for America’s game.

After refreshing ourselves at Lucky’s Sandwich Co. we headed southeast, toward the Lincoln Park Zoo. We took our time heading toward the zoo, laughing, high-fiving, grabbing each others butts – yeah, were the people that do that annoying crap in public – DON’T JUDGE US!

Passing through Lake View, we came across a building that’s striking beauty stood out. Then, I looked a little closer, and saw something all too familiar. It was the Elks logo, ironically on a statue of an elk.

I had worked at an Elks Lodge  through high school and most of college. Unknowingly and unintentionally, Nicole and I had stumbled across the Elks National Memorial and Headquarters. If you are an Elk member and visit Chicago, are around the Lincoln Park area, or are just passing through Lake View, stop into this amazing building. It is absolutely stunning.

After catching some shade in Lincoln Park, and letting our feet air out in the cool grass, we had finally made it to the Lincoln Park Zoo. Another highly recommended attraction – especially if you have kids – as it is free. Enjoy some pictures of the animals – you know we enjoyed taking them.

The cuteness of the animals had taken its tole on us. We exited the zoo on the south side, tired, and knowing we had one more destination that day: The Navy PierWe cruised through the Gold Coast, our pace slowing. The late afternoon sun peered through the trees and landing on some of the exquisite homes and gardens. Some of the cars were worth more than houses I’d lived in. Onward, passed Northwestern University Medical School we rounded the corner and saw the Lakepoint Tower…..

……ONE         MORE             MILE……..

Exhausted, we wanted barbecue. The Purple Pig, that sounds like pulled pork and ribs. So, we trudged another mile. Our feet screamed, we were crabby and in dire need of an increase in blood sugar. Stairs to get there? Excellent. We enter. “A table for two, please.”

“Sure. Inside or outside.”

“Inside.” We needed some air conditioning.

“Right this way.”

We fell into our chairs as the host seated us. Two waters immediately found their way to the table, with a pitcher to fill them. Not that we needed it, because a table busser would top us off every time the glasses were less than 3/4 full. As we searched for the strength to read the menu, we noticed the curious names of dishes. What the…??

Turns out, we had walked into a winery that specialized in artistic culinary dishes, not barbecue. (Four letter words). I had let m’lady down; you see, we’re burger and steak kind of people – especially after a long day. After ordering our drinks, I took a stab at deciphering the menu. I saw beef chips, some sort of corn on the cob, and then something with cucumbers, peppers and feta cheese. The waiter brings back our drinks and approves of my choices. Atta boy, Tee, you may have saved the day, I thought as he walked away.

The beer and water were delicious. But, then, we started to see interesting dishes find their way to the tables next to us. What is that, green corn? Why is there a fried egg on that salad? Is that even a salad? I was in trouble. Nicole looked at me, worry mixed with suspicion. “Hey!” I said with a false confidence, “we’re trying something different this time. It’s about the experience.”

Nicole just laughed and shook her head.

Then, what I would call pork rinds were set in front of us. “Beef chips. Enjoy,” said the waiter as he walked away.

Mouths open, Nicole and I just looked at the dish, then at each other.”Where’s the beef?!” she said.

Boy, had I let her down.

Turns out, the single corn on the cob, split into three pieces and stacked on a plate, with some sort of green sauce was the best “dish” we ordered. And it was only $9!

We laughed it off, ate what we could and left, still fairly hungry. My wallet was a good deal lighter too.

“Wanna grab some McDonald’s?” I joked as we stumbled out of The Purple Pig.

Nic laughed, “It’s just, nothing was what we expected.”

But, at that point, we just wanted to take our shoes off and put our feet up. I put my arm around her and we finished our fifteen-plus mile day with smiles on our face….and a little bit of food in our bellies.

Friday Morning, August 7th, I was hearing “What I got,” by Sublime once again. Nicole was already in the shower. Our final day in Chi-town had arrived.

A skate park in Grant Park, near the famous Agora
A skate park in Grant Park, near the famous Agora

Two days after we had arrived and headed to Shedd Aquarium, Nicole and I took a similar route to the Field Museum. This time, feeling less rushed and more at home, we stopped and admired the statues, the famous Agora, and we even wondered at a pair of shoes that had lost their owner.

It was another bright, sun-shining morning. Our feet hurt, but we still had smiles on our faces. We came back through the park one last time after visiting the museum, which was awesome. I wish we didn’t have to get to the train so soon, we agreed, because we would have spent a whole day in the museum.

We said good-bye to The Bowman and The Spearman, who had greeted us when we arrived at the Congress Hotel, dropped off our bags at the train station and went to have one last meal, Chicago-style.

The place was Giordano’s, and it was the best pizza I have ever had. Seriously, just go eat at Giordano’s, your taset buds won’t be disappointed.

And for dinner, the best pizza I have ever had.
Final Meal, the best pizza I have ever had.

We walked to Union Station, bellies full, admiring the river and soaking in the last bit of Chicago we would experience this time. There was a man with an oxygen tank on the street corner playing the saxophone, and playing it well. What a city…

We could have easily spent five days in Chicago, and that probably would have saved our feet. Even though this trip came on quickly, and we didn’t get to spend but about 48 hours in this awesome place, it was a wonderful adventure. It has also given Nicole and I some confidence for our next adventure – The Carolinas, Smokey Mountains and Nashville.

If you have never been to Chicago, GO! Changing environments are good for you. Get out of your normal routine. Save a few bucks, plan a trip – ANYWHERE!  How many times have you re-watched that episode of How I Met Your Mother? If you do go to a big city, check to see if they have offer a CityPASS, as it will save you money, but, more importantly, time. We only used three of the five attraction passes and we still saved money.

Wherever you go for your adventures, take your time. Plan, and look at the menu before you sit down. Walk, and talk to people. Enjoying conversation with strangers is something I would like to get better at. Most importantly, keep your eyes open, because you never know what’s around the corner.


Keep your eyes open, because you never know what's around the corner.
Keep your eyes open, because you never know what’s around the corner.

*If you have any questions or comments about our trip, leave them in comment section below!*


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