Monday 30th October
The final day of the road trip portion of the trip. We started out in two of America’s great cities and we end it in a third. A long overdue visit to Chicago to update and refresh our City Guide for this amazing City. We were however still just shy of 300 miles from the City, and had a huge drive through the midwest, across the state of Indiana, along the shores of Lake Michigan finally arriving in Chicago.
We had a Really nice hotel booked and were looking forward to returning our car and transitioning back into the civilized world rather than life on the road. It had been a tough trip, but ultimately very rewarding as we traveled to some parts of the country we had not visited before.

Hitting the Road.
We had decided to take the direct route today. We could have taken the longer route up into Michigan, which would have avoided the Tolls, but this would have added over an hour to the trip and we decided to just cough up and go direct.
This means picking up the I-90, just outside of Sandusky, and following it the whole way to Chicago. And we did stick to the I-90 until less than half a mile from the City Center. As far as directions go it could not be easier, however we still managed to get lost!

There really is not much to say about the drive. We had a bag full of snacks, and a playlist of road trip songs and we just hit the road and plowed through, about the only distraction being American driver’s appalling lack of lane discipline, and their innate desire to never be overtaken or use cruise control.
The only real thing of note, apart from a brief stop at a service station for some lunch (Popeyes Chicken was about the only option), was the weather. It started out a bit dull and cloudy and brightened up to glorious blue skies by the time we got to Chicago, however, the temperature had plummeted. We had gone from 90°f (32°C) in Upstate to New York, and now the needle was barely nudging 40°f (4°c) at midday! And the few Rain Sqaulls we passed through before the skies cleared were decidedly white and Snowy!




After a long uneventful slog, the unmistakable skyline of Chicago started to creep into view…After finally hitting the interstate offramp, after 290 miles of pancake flat straight-line driving, we instantly got lost!
The issue really was the insane underground road network that runs under the City. Unmistakable from The Dark Night Film, Wacker Drive is innately confusing to the uninitiated. The problem is, that you are relying totally on signs. There are no visual cues, as you are underground, and the Navigation System simply gives up with no signal. So we didn’t really know where we were going or what exit we needed so were basically driving blind. After 7+ days on the open road, it was a bit of a system shock.
In the end, we just got the hell out of the underground system where we could at least see where we were going. This worked fine, except we were now crippled by traffic. However, after crawling along for a few hundred meters we were finally in the center, overlooking the river, and hunted out the Hotel quite easily. However, this was just a drop-off stop to unload the luggage as we still had to return the hire car. No point in paying city center parking charges when we would not use the car for the next few days before flying out.

So after dropping off the car, we headed out again, this time along Lakeshore Drive to Northhalstead where the rental center was located. We dropped off our little Mitsubishi Outlander, which had been a flawless road companion and headed over to Wrigley Field to hop on the L and back into the city center.
The Pendry Chicago

We emerged from the L station into a frigid and cold Chicago afternoon. While it was cold the air was clear and crisp and the skies were blue and beautiful, the sun was low in the sky but we still had a white until sunset. So we headed to the hotel to check in properly.
We had booked the Pendry Chicago as a bit of a treat. This is a luxury 5-star Hotel in a fantastic location and housed in the iconic Carbide & Carbon Building. We booked this through our AMEX card using the Fine Hotels and Resorts system so we got lots of free perks with the booking. A free breakfast every day, room upgrade, welcome cocktail, and $100 resort credit. Honestly, it wasn’t even that expensive at around $200 a night, so quite a bargain with all the extras.



Unfortunately, we did not get our room upgrade. This was disappointing, but the receptionist explained why, treated us with dignity and respect, and did her best to get us the best room she could in the category we booked. We mention this mainly in contrast to the horrible experience in the Cosmopolitan in Las Vegas where we were lied to and treated as second-class guests because we had dared to book through a system we were entitled to. They never did get that we were not annoyed about not getting the free upgrade, but instead the lack of respect, fairness, and dignity. Anyway, enough of that, and more on the Pendry.
The Stunning exterior is just the start as the communal areas, the lobby, the bar, etc were all beautiful and they were staffed with friendly, polite yet professional staff. Heading upstairs our room was fantastically appointed. It was pretty small, but the bed was divine, and all the fixtures and fittings were high quality. The bathroom was adorned with copious Marble and Stone and had really luxurious feel.
We resisted the urge to melt into the massive comfy bed and instead headed out to explore the City and get the best of the stunning winter light that was bathing the City.
River Walk





The Pedry is located right in the heart of the City and the natural place to head to for our initial exploration was the River Walk. The Chicago River runs right through the heart of the city and the River Walk offers some seriously stunning vistas and architectural views. So we headed to one of Chicago’s famous swing bridges and then down onto the river walk.
it was getting bitingly cold now, but the sun was doing just enough to keep the intense cold at bay but to be honest, we were ill-prepared for this level of cold.
As we strolled down the river the stunning concrete canyon of the city really took our breath away. The river ferries were chugging up and down the river as the sun began to fade and start coloring up the evening sky.
We got as far as the Lakefront Trail, offering views out over the Lake, the Navy pier, and back up the central canyon of the City. We had intentionally planned no activities for this afternoon as we didn’t want to have added time pressures on the drive-in, so we just took our time talking back up the other side of the river taking in the real splendidness of the City.


Back near the Hotel, we spotted a local hero from back home…namely Primark! This Irish clothes store is just starting to make its mark in America, but back in the UK we are all well aware of Primark and what it offers, super cheap but still decent clothing options. This seemed like the PERFECT place to stock up on some winter essentials, just in case the weather turned even more wintery (stay tuned as we have a big surprise in store!).
Note – For reference, the name is pronounced PRY-mark, not PREmark, just so you Americans no as you seem intent on butchering the name before it’s even got a foothold…
Chateaux Carbide
Now kitted out with $5 winter hats and gloves we headed back to the hotel to make use of some of our $100 credit. The first stop was the Lobby bar where we toasted our arrival with our free welcome drink. This was just a fruit soft drink but our Check-In agent told us to take the drink to the bar where they would spice it up. A shot each of Tequila and the slightly blad punch had a real kick.



We then headed upstairs to the hotel rooftop Cahtaux Carbide. This plush indoor/outdoor rooftop space offers dazzling views of the City below along with handcrafted cocktails specializing in Absinthe-based drinks, something we don’t often come across in the US!
The indoor portion of the bar was ok, but quite small and only really a glorified welcome area. This would be fine, but as we mentioned temps had dropped suddenly, and now, during the evening, it was really cold right down to the low 30’s (zero°C). This meant the outdoor area was bitterly cold.



The view was stunning, and the outdoor deck was really nice and well-equipped with cool selfie spots and set pieces. It looked out over the river and downtown Chicago and was basically wonderful, but damn was it cold. They had a few fire pits but these really didn’t scratch the surface. This meant our outdoor time was limited, we just took in the view, grabbed some nice selfies and photos of the city, and then scurried back in to warm up. We can just imagine how wonderful the space would be on a warm summer evening.
Deeppan Pizza – Lou Malnati’s
After a drink in the bar, we headed out into the City to get some dinner. In Chicago, there is always one thing on our minds, something that is scarcely found elsewhere and worth hitting the City for all on its win…Chicago Deep Dish Pizza. We had a few meals in the City but could not think of any reason to wait any longer. As we had such a beautiful hotel room we figured it was worth grabbing a takeaway pie and just chilling in our little slice of luxury with our little slice of Pizza.
Just across the Dusable Bridge in the Wrigley Building was the famous Lou Malnati’s Deep Dish Pizzeria. No One is 100% sure who invented the Deep Dish Chicago Style Pizza, but Rudy Malnati most certainly had the leading hand in popularizing it with the masses. Some say he invited it when working as a Chef at Pizzeria Uno, others have different ideas but it was certainly Rudy who took it to the Masses and his chain of restaurants Lou Malnatis’ (named after his son) is one of Chicago’s most popular jints.


We headed in and ordered a Large Malnati Chicago Classic™. This 6000Kcal monster was probably a bit much and it took a good 40 mins for them to bake. It made my arms ache slightly carrying it back to the room.
We took on this colossal feast between us despite it being designed for 4 and felt utterly stuffed. A real decadence as we took the evening off to try and digest the monster.
A big day awaited us tomorrow and we needed a nice bit of downtime to relax and take in the new setting. Tomorrow we unleash another City Pass as we take on the best Chicago has to offer. and we had a bit of a surprise in store for us as we ate breakfast the following morning.
Walking Total – 15,415 Steps – 8.2 Miles
Seeing as we spent most of the day in a car, we were quite surprised to rack up this many steps. Our hike up and down the Riverwalk was only around 3 miles, so where the other 5 came from we are not too sure…
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Day 14 – Chicago – Sightseeing in the Snow – Halloween Parade >>>
