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The Whiny Hiker’s Guide to the Big City: Visiting Chicago

The Whiny Hiker’s Guide to the Big City:  Visiting Chicago

My list of DOs, DON’Ts and Well Actuallys…..

The last time I found myself visiting Chicago, it was around 1980. I was riding in the backseat of my mom and dad’s 1977ish Chevy Chevette with a sister one side, a brother on the other and a littler brother that rode part of the way lying on top of the luggage in the hatchback. Apparently, seventies parents weren’t concerned with car seats, safety or comfort for that matter. (I don’t even know if baby/toddler car seats were a thing way back then.)

I remember these big trips that we took which often was a business trip mixed with a little vacation. Now that I’m a parent and after traveling a lot with my own boys, I know how hard it is to travel with youngsters and how hard it must have been traveling with four small children all within 7 years of age. I’m not sure how much of a vacation it was but we still had a lot of fun.

Our humble chariot
Photo: Pinterest

But I remember that day my dad drove us into the big city and seeing the Chicago skyline for the first time. At that time in my life, the biggest city I had been to was Nashville probably. It was a big deal to little country bumpkins from little ol’ East Tennessee to see those skyscrapers. I remember staying at the Drake and going to the beach on Lake Michigan. We left a humid and hot Tennessee that summer and found a windy, cool spot on the beach on Lake Michigan. The water was so cold that my mom wouldn’t get in. I can also remember a trip to the top of the then Sears Tower. That must have been another hair raising experience for my parents. It was probably a lot like wrangling cats. It’s probably why my daddy’s hair turned gray at about 30. But whatever happened during our visit to the Windy City, we all have fond memories of those experiences. I’m sure my parents have put away the memories of how difficult it was to load up a passel of kids, the cost of sheltering and feeding them, not to mention how tough that 9 hour drive would’ve been in a Chevette! I think my mother put a chiropractor on retainer after that trip.

So now we all just remember the fun stuff and cherish that we had good times together. My younger brother may not have all those warm fuzzy memories. He may have suffered a little carbon monoxide poisoning from riding in that hatchback for 9 hours. Don’t worry about him, we probably let him ride in the floorboard some too. He was alright!

Because I do have fond memories of visiting Chicago from my youth, I jumped at the chance to go back there recently. The Sheriff had never been and there were some super cheap plane tickets to be had so we had a plan! We even talked our youngest son into going with his old folks on a short jaunt to the Windy City.

Now you can glean a plethora of information from Pinterest about must dos, things you can’t miss, top ten mistakes you make and other posts travel bloggers write-all great information. Read it, take it to heart and write it all down. We took a lot of that information and set out to find out what shenanigans we could get ourselves into.

First things first about Chicago-you will walk! The absolute one “must do” or “must have” is at least one pair of really good shoes. DO bring two pairs of really comfy walking shoes if you have room. I’m going to say it again for those in the back. You will be walking a lot! You will want to walk. Trust me! DON’T be like us and think you need a car. You don’t unless you like to pay for your rental car, toll pass and $50-60 per day to park. Parking is a lucrative business in Chicago and you will pay handsomely to park. And when you do park your car, chances are you won’t be able to go in and out and the lot may not even be next to where you are staying. There is an app! Spot Hero will help you find cheaper parking but you probably won’t be able to move your car as you wish. So maybe just skip the rental car and catch the train to your destination. WELL ACTUALLY, you might want to get a car for a day trip or two because there are some awesome places that you can skip off to. I’ll tell you about a couple of those places too. If you do want to rent a car, most of the downtown hotels will have a concierge to set that up and there were several rental places downtown to serve your needs.

Now this next part is going to be a shocker. We started our sight seeing at Millennium Park and Art Institute of Chicago. I know, I know, you don’t think of us as the artsy type. You’re right, but we can enjoy the historical aspects of famous painter, sculptors and beautiful pieces even if we don’t know exactly what we are looking at. Millennium Park is the home of The Bean which is actually not its correct name. The correct name is Cloud Gate and obviously it is a must DO. You have to post a reverse selfie from the Bean on Instagram. All the cool kids are doing it.

Inside the Institute, you can meander through beautiful sculptures and art from all over the world. You can see famous originals such as the American Gothic. DO take a fully charged phone to take lots of pictures. I walked through a lot of the museum before I realized I could take pictures. And then my phone died before I got to the Picasso’s. DON’T fret if you don’t find all the “featured” paintings from the museum guide. Some of them are in galleries in other buildings or not arranged in with other paintings of the same artist. For example, the Georgia O’Keefe Sky Above the Clouds painting is on wall outside the gallery where the rest of the collection is displayed. However, you aren’t likely to miss that one because it’s HUGE. DO listen very closely if you ask one of the employees for directions. I got a little confused when the directions included “you will walk through gallery 243 and pass a painting on the wall…”. Seriously, Mr Art Guard Employee?? I need you to be a little more specific. DON’T give up, though, on finding the featured Picasso painting, The Old Guitarist. There’s a great backstory there. I won’t spoil it but do look for the hidden faces.

Picasso’s The Old Guitarist
We survived!

Willis Tower (Formerly Sears Tower) is definitely on all the must DO lists and rightfully so. I’m not sure any trip to Chicago would be complete without a 60 second elevator ride to Floor 103. It is one of the most terrifyingly terrific experiences to be had. DO stand in line for the Ledge. Albeit unbelievably scary, it is well worth your time. When else will you feel as if you have defied gravity by hovering 1353 feet over the big city below? DON’T take your super smart, millennial, engineering student of a son. You are likely to be freaked out by his analysis of the structural integrity of what supports that ledge of glass you are about to step onto. WELL ACTUALLY, do take him. He is going to take care if you when your old so he will probably hold your hand if you’re scared.

**Something you may not know when you visit the Willis Tower. The staff at Willis Tower are friends of Law Enforcement, meaning they may let LEO’s and their families in at no charge. We were offered the perk but had already purchased our tickets as a bundle at the Art Institute. If you are Law Enforcement and traveling with your family, check with security before you go.

The Navy Pier is one of those places some people say leave off your must do list. I would definitely encourage a trip to Navy Pier but again be prepared to pay for parking unless you learn to navigate the L or want to walk a long way. DO eat at Giordano’s. You can get your deep dish pizza here and won’t have to fight the crowds that gather at some of the other locations. DON’T feel obligated to eat the deep dish pizza because their thin crust pizza is amazing and not so thin at all. DO be prepared to wait 45 minutes while your deep dish is being prepared.

Navy Pier also has several other attractions such as a giant Ferris Wheel along with some other amusement park type rides. You can walk out onto the pier and get a glimpse of Great Lake Michigan. It’s a beautiful view and a relaxing experience.

DO research the different neighborhoods. Each neighborhood seems to have its own unique personality. You might want to pick where you stay based on what the neighborhood has to offer. We stayed in the South Loop neighborhood which seemed to be a centralized location to walk or catch the train Once you’ve walked all over the city, it’s a great place to hang out. You’ll find delicious places to eat such as Hax Burgers, Gordo’s Ice Cream Bars and you can get an excellent Chicago Dog at Rudy’s.

Now for the side trips. Side trips are usually part of our traveling. I always like to add different states to my list of hikes while doing the 52 Hike Challenge. It gives you a sense of adventure plus you get to know places you may not have been before. So I’m always scheming to find how close we are to neighboring states when we travel. If we can fit one in, then I can add another state to our list.

There are a couple (I’m sure there are so much more than a couple) of very interesting places within an hour’s drive of Chicago. We took off one day to Milwaukee. It was a very nice change of pace from the busy big city plus there’s cheese! The Smartest Boy in the World was in heaven sampling Wisconsin cheeses at the Wisconsin Cheese Mart on 3rd street. You can even buy cheese that is packaged and ready for travel. If you buy over a certain amount, and we did, you get a nice little cheese cooler to make sure your cheese makes all the way back home.

Milwaukee is also set on both sides of a river so it is a nice walk along the river watching the boats navigate the city and their bridges. A must DO on my next trip is a boat ride along the river to view the beautiful skyline. And when in Milwaukee, DON’T forget the Bronze Fonz!

Another great side trip is the Indiana Dunes State Park in Chesterton, Indiana. You will find giant sand dunes, a great view of Lake Michigan and the beach. Any place with the beach is alright with me. DO check local information before you go because swimming is not allowed after a certain time of the year. WELL ACTUALLY, that water was really cold….

I could just go on and on about this trip and these side trips we took. There is so much more to do and to be done. We will definitely being going back. And as much as we love visiting the big cities, we are always happy to get back to our neck of the woods to catch our breath before our next outing. Visiting Chicago is going on our list of favorites. Check out my Instagram and Facebook pages with more pictures from our trip. There are some super cute pictures of my traveling buddies and you can see how great my son doing with his chemo.

Share with me some of your best places to eat, things to do and must sees in Chicago or your favorite big city. I may want to add it to my bucket list!

Follow the Whiny Hiker and her crew on Instagram, Facebook and Twitter (my Twitter is not that interesting, just sayin’) to stay up to date on shenanigans, ghost stories, ridiculousness and family fun. Also stay tuned for Whiny Hiker stuff-we’ve got some stickers and other things coming down the line.

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