Road Trip Diaries, Day 1: On the Way to Chicago, and Staying in an Inverted Spyglass

Welcome to our road trip diary! This first entry will just cover our drive from Arlington, VA to Chicago; later entries will cover our journey on old Route 66.

Saturday, July 23 – Day 1 of our big road trip found us up early to hit the road for an 11+ hour drive from Arlington to Chicago. We had rented our car the day before. Enterprise didn’t have a standard available, so they upgraded us to an SUV for free – a silver Toyota RAV4. It was comfy enough, roomy, and promised to be able to handle the rough roads of old Route 66 well. The sound system left something to be desired. Oh well, we had a ride! On Saturday morning, after a breakfast of McDonald’s, we were off! I love the first few moments when you hit the road for a vacation and the anticipation is at its height.

Our travels took us through Virginia, Maryland, Pennsylvania, Ohio, and Indiana – a new state for me, but not Eric – before finally reaching Illinois and Chicago. Eric is a pro at long drives (literally), and I had done all of the research and planning for the vacation, so that set us up as driver and navigator, respectively. I figured we’d switch at some point, but we never did!

We racked up plenty of tolls along the way as we took the fastest route of the Pennsylvania and Ohio Turnpikes, and the Indiana Toll Road. I had been down the PA Turnpike several times before and enjoyed seeing the cows, pastures, and mountains once again. At one point we could see a big herd of cows laying in a grove of trees to stay cool. At another, we saw a Pokemon Go player shuffling creepily through a wide open field, smartphone in hand … or maybe it was a zombie. We drove past the wind turbines of Johnstown. But my favorite part of the PA Turnpike is probably going through the Allegheny Mountain Tunnel.image

The Turnpike travel plazas are great, as you don’t have to exit and pay the toll just to get gas or use the restroom. The one we stopped at (North Somerset) was crowded – though not all that bad for a summer Saturday. I was expecting it to be way worse than it was. We picked up pretzel dogs from Auntie Anne’s and a couple of drinks and moved on.

The Ohio Turnpike’s travel plazas were much bigger and nicer (sorry PA) although the scenery was mostly just mile after mile of flat land and farmland. At Erie Islands plaza, we picked up Einstein Bagels for an early dinner, and then Eric found a crane game with an orange dino skeleton that would pick up your prizes for you. I won two things – a goofy wind-up turtle, and a triceratops figure with bright red painted eyes that looked kind of demonic. Eric left the former on the machine for a lucky child to find, and I kept the latter for myself … he was too creepy not to take home for future Halloween decorations.

By the time we reached Indiana, I was getting really punchy and doing this thing I do where I crack up for no reason. We saw more cows and calves running around. We started getting pelted with rain. It was mile after mile of cornfields until we got to the Gary area, but it was very pretty. Originally a country girl myself, I found it relaxing. Also, by this point we’d seen a couple of other interesting vehicles on the road – a car with a Route 66 license plate, plus these guys …


This antique car first popped up as early as PA … by Indiana we were still driving alongside it at times!


Check out this awesome Mayberry Sheriff’s Car! Look in the window and you’ll see it’s Barney Fife’s …I loved The Andy Griffith Show as a kid.

At long last, we reached Chicago! The traffic heading into the city was very slow, but no worse than DC’s. The skyline was gorgeous and made the long drive much easier. The sight of the Willis Tower (formerly the Sears Tower) looming over everything is especially stunning. There was no way to really capture how incredible it was with my camera. We soon learned from walking around the city that Chicagoans are very proud of their architecture, and they have every reason to be. Unique, well-preserved historic buildings are everywhere and they are beautiful.


The Chicago Skyway Toll Bridge

We noticed a super skinny skyscraper as we headed into the heart of Chicago’s Loop area, and it turned out that was our hotel, the River Hotel. We  dropped off the car with the friendly and extremely helpful valet (and left him a good tip). The price to park valet seems extremely high in Chicago, but the alternative was for us to fumble around in a cramped parking garage ourselves and then haul all our bags … and the garage by itself, no valet, was still very expensive. We checked in at the front desk so late that they actually didn’t have any rooms left in the River Hotel itself, so we got upgraded to the Club Quarters hotel in the same building – and grabbed the very last room. They had oversold and that meant everyone after us would have to be walked over to neighboring hotels.

If you’re wondering how two hotels share the same building, it’s kind of a unique story (at least, it’s the first time I’ve ever encountered this). Our hotel is part of a building known to Chicagoans as “The Inverted Spyglass” – a nickname for the historic Mather Tower (later known as Lincoln Tower). The building was nearly torn down a few decades ago, and in fact, the original four-story cupola was removed. (It’s since been replaced with a new one.) The River Hotel has the rooms all the way up to Floor 10. Club Quarters, which provides hotel rooms for corporate members, has rooms in the octagonal part of the tower starting at floor 11. We were on floor 23. The octagonal tower is very skinny, so our room was small, but very nice for what it was. At the rate we were paying – a downright bargain in the heart of Chicago, right on the River and easy walking distance from Millennium Park – we were not complaining. Our bed wasn’t super comfortable, but it was good enough. The bathroom was tiny, but everything worked, the shower was deliciously hot, the amenities were nice, and most importantly, it was very clean. The room came with a small stash of library books, and there were reusable water bottles out in the hallway with a chilled water station. (I’m also remembering now that they offer free aromatherapy sleep kits and I meant to request one and completely forgot!) The view out of our window faced some great looking skyscrapers. Finally, the downstairs lobby was beautiful. Great attention to detail was paid when renovating this building – it was clear there were originally six elevators, now reduced to four, but the two old elevator spaces in the lobby were cleverly re-purposed as a brochure cabinet and a business center. The gorgeous old elevator dials were left alone even though they no longer worked! A warm and inviting lounge was around the corner with water, coffee, and comfortable chairs. There was also an Italian restaurant downstairs. For Day 2 we had plans to get up early, and we were exhausted from our drive, so instead of eating there, we pretty much just took a shower and crashed.

Day 1 Linkage: 

The view from our hotel window

The view from our hotel window


One response to “Road Trip Diaries, Day 1: On the Way to Chicago, and Staying in an Inverted Spyglass

  1. What a great trip, and it’s only the first day! I do love me some Auntie Anne’s pretzels!

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