Someone told me recently that hotdogs are the start of every great story. Now, I’m not sure of the accuracy of that statement, and this one doesn’t really begin with hotdogs…but there’s a hotdog in it. So it qualifies, right? Last week, I expressed my anguish at having missed out on a Seattle dog, so when I visited Chicago, Illinois, a few weeks later, I made sure to not make that detrimental mistake again! Okay, so this wasn’t my first time visiting Chicago, and it definitely wasn’t my first time eating a Chicago dog, but there are some food staples that you can’t miss in each city. Hotdogs just happen to be one of them…again.

A good portion of my extended family live in the Chicago area, so I have spent pretty much my entire life driving between this great city and my southern home in Atlanta. However, generally speaking, since my usual visits involve major holidays and lots of family time, my time playing tourist in downtown Chicago has been limited. One of my good friends growing up and I always talked about driving up to Illinois and playing tourist, but never really made the trip happen…until we both found ourselves with nothing to do but enjoy life back in May!

Did we plan this trip only a week in advance?


Was it worth it?

Let me paint a picture for ya. A young girl finds herself lost for a moment in life, not really sure what to do next. She just wants to skip town and find some adventure somewhere and maybe find herself along the way. She rendezvous with an old friend, only to realize that they are both in the same boat, so these two young friends, two fish in a wide ocean, venture off into the grand unknown to harness life by the…

Do I sound like a cliché yet??? The short (and less annoying) answer is yes. We had so much fun! We were working with a relatively short time frame and a relatively small budget, so we stayed with family and took the commuter rail into the city, for a few days of sightseeing and skylines.


Before our visit, we picked out a few big attractions, and prioritized our visit accordingly. And since we were staying outside the city with family (meaning an arduous train ride into the heart of Chicago each morning), we were forced to really hack away at the amount of sights we would be able to enjoy in our short two or three day stay. So, when we hopped on our first train somewhat later than planned due to a geographical error, we had a general plan for what our day would look like.

Skydeck at Willis Tower

Does it bother anyone else that Sears Tower is no longer Sears Tower? Just me? Cool. Willis Tower, the artist formerly known as Sears Tower, was once the tallest building in the world, standing at a whopping 108 stories tall. It was surpassed after 25 years of holding the title, and now follows New York City’s One World Trade Center as the second tallest building in America.

Our ultimate goal for this trip to Chicago was to indulge in all things touristy, and nothing made me feel more accomplished than departing from the train station, being partially blinded from my hair suddenly whipping around my face, and heading straight to Sears Willis Tower! They don’t call it the Windy City for nothing, people. The grandiose skyscraper will call out to you on the sidewalk, but be sure to use the entrance on Jackson Boulevard to get in line for Skydeck.

Are you looking for honest truths? I hope so, because here is one: you will wait in a ridiculous line for this observation deck. There is no getting around it. Buy your tickets online and you might cut 15-20 minutes off of your wait, but you will still wait. Buy the fast pass to go directly to the elevators, but guess what? There will be a line at the elevators. And a line at “The Ledge.” Skydeck tested our patience more than anything else we did in this city, but luckily it was our first adventure and our spirits were high! Before committing to the wait, there is a sign at the entrance showing estimated wait times. The sign guessed a 60-90 minute wait for us (and keep in mind that this was around 10am on a Monday—I can’t even imagine the wait on weekends!), but in reality we stood for about 45 minutes before reaching the elevator up. There is a security check along the way to the ticket counter, so even if you purchase your tickets in advance, you will still be subject to this. However, if your budget is grand and you are too good for lines (more power to you!), you can dish out the $50 for a Fast Pass, in which case your wait will be closer to ten minutes for just the elevator. The website recommends arriving prior to open in the mornings for the shortest waits.

When we reached the observation deck, we were greeted by beautiful views of the city on all sides! Skydeck is 323 feet higher up than its rival observatory at the Hancock Center, and also holds the popular glass boxes that extend out from the floor on one side. Known as “The Ledge,” these boxes have glass floors, which allow you to look down over a thousand feet to the ground while you hover above. If you are like me and this makes your heart race uncontrollably, know that The Ledge is equipped to hold five tons, and don’t look down until you’ve become comfortable in your little glass home! You can do it! We only waited in line for about 15 minutes to experience this.

The other three walls on the 103rd floor are all windows. I really enjoyed the maps that were stationed intermittently around the room that identified well-known buildings and landmarks within view. It was a great way to get to know the city at the beginning of our stay!

Chicago Pizza: Part One

Once we had become adequately acquainted with the view, we descended back to the street in search of our culinary mission numero uno: Chicago style pizza. Chicago deep dish pizza is more unique than any other style of pizza that I’ve tasted. Because of this, it’s much harder to find true deep dish pizza outside of the Chicago area than it might be to find, say, New York pizza outside of New York. Luckily, there are hundreds of reputable places in the city to find this tasty treat, and so we were able to literally walk across the street from Willis Tower and into a Giordano’s for lunch. And my travel buddy tasted her first Chicago Pizza!

I have heard that Chicago has a bustling food scene, but I have never really stuck around long enough to branch away from this staple. Sorry guys, I came for the pizza.

The Bean and Millennium Park

The post-lunch plan was to not have a plan. We walked down to the park area to Buckingham Fountain, which is a fantastic spot for people watching. The weather was so beautiful that we continued on foot to Cloud Gate, more popularly known as the Bean.

The Bean was constructed by the very famous artist Anish Kapoor in 2006, and has been a Chicago icon ever since then. The gigantic public artwork is made from stainless steel and seamlessly reflects and distorts not only the city skyline, but also the image of the viewers around it. Because of this, it is a very popular photo op for visitors and is incredibly crowded. Always. Don’t let the hoards of people keep you away, though! Millennium Park is beautiful and well kept, and FREE. You can spend as much time trying to get the perfect shot of the Bean, but you may have to come to terms with the fact that everyone else is trying to accomplish the same goal as you. Embrace the crowds at Cloud Gate. As an art enthusiast, I like to think that the Bean helps to close the gap between art snobs and the rest of humanity.

So we played around at the Bean for a little while, walking underneath and taking plenty of photos and selfies. We got truly lucky with the weather that day and soaked up as much sun as possible! Our wanderings took us out of the park and toward Navy Pier, where we stopped briefly for a drink before catching an Uber to our evening activity.

Wrigley Field

The Cubs game was the only event for which we bought tickets in advance. I was really excited about this, because I had never visited Wrigley Field before! It’s in a cute little neighborhood called Wrigleyville, and our driver dropped us near Gate D. We didn’t spend much time outside the ballpark, except to purchase some shirts (my very first sports team shirt, you guys!). We met up with my aunt, a local and avid Cubs fan, at our seats. Our nosebleed seats were situated by first base and I didn’t feel like I needed binoculars in order to see the game. They were also covered, an added bonus since the evening became a little rainy as the sun went down.

Wrigley Field is the oldest ballpark in the national league, and the second oldest in America, after Fenway Park. It still holds onto that charm with the functioning hand-turned scoreboard, not to mention the ivy-covered outfield wall. Being in a residential neighborhood, there are buildings just outside outfield, which also host seating from which you can watch a game. Those seats were empty for our Monday night game, and old timers (here’s looking at you, Dad) will reminisce on a time before those buildings realized they could be pulling a profit and you could bring your own lawn chairs to watch games for free!

We had stadium food for dinner at the game, and took the bus back toward the parking lots afterward. There are not many parking decks or lots nearby, so buses are employed to shuttle fans back to the parking lots a few miles away. I believe that this lot on Rockwell Street is free. Since my aunt drove out to meet us at the game that evening, we hitched a ride back home with her that evening, rather than taking a train.



Due to our late night at the ballpark, we decided to catch a later train into the city on Tuesday, and arrived in downtown around noon. It was a much more blustery day with rain on the horizon, and so we embarked on an indoor adventure for the afternoon—my activity of choice, the art museum!

The Art Institute of Chicago

My home in the Southeast United States is known for a lot of things, but art museums is not one of them. The Art Institute of Chicago is a much higher quality museum than what I have access to at home, and I was really looking forward to checking out what it had to offer.

It did not disappoint.

There was no line for tickets when we arrived, which we purchased at the counter, and then paid the extra dollar necessary to check our bags. This museum is BIG and full of names and paintings that everyone can recognize.

We started on the top floor with Impressionism and slowly worked our way around, ending in the modern exhibit. The museum holds work by Monet, Van Gogh, Renoir, and Rodin, to name a few. It is also very well rounded and has exhibits devoted to art from all over the world, as well as exhibits dating back to ancient times all the way up to contemporary work. We stopped for a quick snack at the café on our way to contemporary exhibit. I was very inspired by the work of today’s artists, but my counterpart not so much.

We very quickly strolled through the first floor. Having spent so much time taking in everything on the second floor, we were somewhat worn out by the time we went downstairs. Even still, we spent a little under four hours at the museum…if that gives any indication to size. I personally wouldn’t try to plan to do too much else on the same day as the Chicago Art Institute of you really want to see the art. It takes a lot of time, but it’s totally worth it!

Chicago Pizza: Part Two

Back out on the streets of the city, the rain let up briefly while we meandered toward the parks again. However, it wasn’t long before dark clouds and heavy rain forced us back inside. This time, we landed at Lou Malnati’s for more pizza. We were meeting a friend who lived in the city for dinner later, so we ordered a pizza to go and shared a salad while we killed time and waited out the rain.

We took our pizza with us and walked to Vice District Brewing Company on S Michigan Ave, a BYOF tap room. Our party of two grew to three and we enjoyed our pizza over flights of beer.

Signature Lounge at the Hancock

After dinner, we stopped one more time at the Bean on our way to our final destination for the evening. It was much less crowded that evening than it had been the day before, but I don’t know if credit goes to the time of day or the weather. We didn’t stay long and kept on up Michigan Avenue toward the Hancock Center.

The Hancock Center holds Chicago’s other observatory, 360 Chicago. Just above the observatory, though, sits the Signature Room and Lounge on the 95th and 96th floors. We took the elevator up to the Lounge for after dinner drinks and were greeted with a stunning view of city lights. I checked out the drink menu ahead of time to prepare myself for the damage that this place might do to my wallet, to find that beer and wine were reasonably priced between $9-20. In comparison to the prices we paid and lines we waited in at Skydeck, $10 for a beer with a view was absolutely doable.

We were able to snag a small table next to the window, where we spent the rest of our evening. It was a really wonderful way to end our day in such a beautiful city.

We stayed as late as we could, catching the final train back out of the city to our home base that night.

Day Three

We had one more day before we had to come home, but we spent it outside of Chicago with family. Still wondering about hotdogs? We had Portillo’s for lunch in order to satisfy all Chicago food necessities! Our road trip was short and sweet, but a great (and relatively cheap, considering all of the tourism) getaway, and an opportunity to explore an area that already feels familiar.

You’re looking good, Chicago, as always. See ya soon.



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