The Loop

Well, this morning started off a bit differently to how we'd planned! Jane popped up to the shop early and decided to buy a scratch card for the lottery while she was there – and only went and won $1000 on it! Talk about a surprise! So, suddenly, the urgent priority for the morning became figuring out how to collect those winnings before we did anything else. Time to get our hands on the cash! "Show me the money!" seemed like the appropriate motto for the start of the day.

Winning Ticket

Inside The Thompson Center
Fedral Building

It turns out the lottery here is run by the state, and to get your mitts on larger winnings like that, you have to go to the federal building in The Loop to cash it in. It's actually a bit of a mixed-use place inside, with shops on the ground floor and offices for various companies around the sides. The middle part is this huge open space where you can look right up about fifteen floors to the very top, with glass-fronted, or 'scenic', elevators running up a big column on the far side. Like pretty much all federal buildings these days, you have to make sure you have photographic ID with you and go through metal detectors because of all the shootings that have happened in the past and general terrorist threats.

I decided to hang about downstairs in the lobby rather than go through the metal detector and get frisked, but Jane had no choice and had to go through. It seemed like she was in there for absolutely ages, though I suppose it was only about thirty minutes or so in reality, until she finally came back down with the cheque. What we hadn't realised beforehand was that you have to pay tax on your winnings here, and that tax rate is about 30%. So, what had started off as a nice round $1000 quickly turned into just $701 after the deduction.

$700 After Tax

But wait, they still weren't quite finished with us yet! Because it was given as a cheque rather than cash, we then had to actually cash it somewhere, and they charged us another $12 just to do that! So, after all the unexpected deductions and fees, they finally gave us what was left of the winnings.

The money was all handed over in crisp $100 notes. They don't even seem to like changing $50 notes in shops here, so we knew immediately that trying to get rid of $100 ones was going to be some fun and games! We ended up having to go and get it changed at the bank eventually, just to get some smaller denominations we could actually use.

Still, despite the tax, the fees, and the hassle with the big notes, we were obviously a lot better off than when we'd woken up that morning, which was the main thing. And the best part was, of course, that lunch was now officially going to be on Jane today!

The Loop

Calder's Flamingo

By the time we came out of the federal building, it was indeed lunchtime – on Jane naturally, given her earlier stroke of luck! So, we started walking down towards the centre of The Loop and decided to drop into Wendy's for a bite. It's a bit similar to McDonald's, and we ended up having cheesy fries and a large coffee there. After fuelling up, we walked just a short distance to this huge piece of artwork in a plaza called Calder's Flamingo. Honestly, I'm not entirely sure where the 'flamingo' part comes into it, as it looked way more like a giant, forty-foot-tall spider to me. But then again, I suppose that's just modern art for you, isn't it?

One Of many plaza's in The Area

While we were in the area, it seemed like a good opportunity to pop into the US post office that was right next to the sculpture that looked like a big spider. Their post offices are quite a lot like ours back home, but everything seems supersized – they have way more counters, but there still seems to be hardly anyone actually serving, so you always end up waiting a while just to buy some international stamps for postcards. However, they do differ from the UK in a couple of slightly surprising ways. For one, the security guards inside are carrying guns, which is a bit jarring. But on the plus side, they also have tables with free Sellotape and boxes you can use to wrap your items if you need to – you certainly don't get that back home!

The funniest thing though, was that even though it was August, they still had international Christmas stamps on sale! These were the exact same ones we'd seen and bought in San Francisco right at the beginning of the year, and they even had "2013" printed on them. I can only assume they weren't exactly flying off the shelves for the US mail service!

Federal Reserve Money Museum

From the post office, it was only a short walk to the Federal Reserve Money Museum. As the name suggests, this place is all about money, and it's located in another federal building, sigh. That meant, just like earlier, you needed photo ID and had to go through a metal detector to get in. There definitely seemed to be a bit of a theme going on today involving money and metal detectors, didn't there!

Looking (at) A Million Dollars

We both genuinely really enjoyed it in here. Even though it's not a huge place, it does a brilliant job of showing you the history of how modern US money came about and how they actually make the notes and coins. There are some fantastic displays, including one where you can have your photo taken by a security-style camera standing next to a briefcase with a glass top that contains a cool million dollars – and they even print the picture off for you for free! They also have a massive glass cube right in the middle of the floor, absolutely stuffed with a million dollars in one-dollar bills, and it’s huge! As a little souvenir, they even give you $500... but it's been shredded and put into little bags for you. 'The Fed' shreds are free!

1 Milliom In $1 Bills

There were loads of other interactive bits too, like using magnifiers to examine notes up close and try to work out which ones were fake. These were all real examples, and some of the fake money was honestly virtually impossible to tell apart from the genuine stuff. I think we happily spent a couple of hours in here, and you really can't grumble when it's free! One thing I was particularly grateful for was noticing just in time that I didn't have my watch on anymore. I'd had to take it off to go through the metal detector, and things like that usually go through the X-ray machine in a separate tub. Somehow, it must have fallen out of my hat that I'd put it in and got stuck in the machine. When it finally 'spat it out', they brought it through, and I luckily spotted it right there on the clerk's desk inside. I would have been absolutely gutted if I'd lost my smartwatch after only having it for a couple of months!.

Looking For lunch In The Loop

By now, it was definitely time for lunch. On Jane, naturally! We were both pretty hungry but didn't actually have anywhere specific planned to stop. Thankfully, you're certainly not short of places to feed your face in Chicago, so we just started walking roughly towards our next planned stop, which was the Willis Tower. There were plenty of eateries around that area, but nothing really grabbed our attention until we stumbled across Luke's Italian Beef. It certainly wasn't fancy by any stretch of the imagination, but they seemed to have the sort of food we were in the mood for, so we decided to give it a go.

It turned out to be a brilliant choice! I went for something called a pot pie pizza, which is basically like a really deep-filled pizza, and it was absolutely lovely. Jane had the ravioli, and honestly, we'd never seen bits of meat wrapped up quite that big before! Chuck in a couple of drinks, and the whole lot came to less than $20, which is only about 13 quid – all courtesy of Jane, of course! These are exactly the kind of places we like to eat at; the food is excellent, even if the decor looks a bit old and worn out, which seems to put some people off. But when the food is this good, who needs anywhere fancy anyway? I also found it quite amusing that they served the food on these sturdy, almost 'prison-style' plastic plates – just like they probably have in San Quentin prison in California! (Not that I've ever spent any time in there, obviously. Ha!)

The Willis Tower

The Willis Tower

After a refreshing lunch, it was just a short walk to the Willis Tower. You might remember it as the Sears Tower, or perhaps you recognise it from its famous appearance in the movie Ferris Bueller's Day Off. While it is no longer the tallest building in the world, it still holds the record for the highest observation deck in the Northern Hemisphere. Sitting at 1,353 feet above the street, the view is incredible—to put that in perspective, you are standing a full quarter of a mile up in the air!

The tower consists of 110 floors and stands 1,450 feet tall. If you include the twin antennas on the roof, it reaches a massive 1,729 feet. The structure was built between 1970 and 1973, but its name was officially changed to the Willis Tower in 2009 after a new company took ownership of the building.

Today wasn't exactly blessed with crystal clear blue skies, so we knew the view from the top would probably only stretch out about thirty miles or so. In a way, though, it kind of worked out better. On a perfectly clear day, you can end up queuing forever just to get inside, but today there weren't too many people heading up, which was a nice bonus. As is standard with these sorts of major attractions, you had to go through a metal detector first, and then you make your way towards the elevators. While you're heading that way, they have displays detailing the history of the building and explaining how they actually went about constructing something quite this enormous. 

Interesting little fact: apparently, there are 900 toilets in the Willis Tower!

Obsevation Deck, Floor 103

Anyway, the lift ride up to the top is seriously fast, lasting just over a minute. You can really feel your ears pop as the air pressure changes on the way up. Most people, though, are glued to the screen above the door, which shows you how many floors you're zooming past and even highlights other famous buildings around the world you would have already gone past if you were travelling horizontally at that speed, like the Eiffel Tower. So, after just sixty seconds, you step out onto the 103rd floor, and wow – what an absolutely incredible view over the city!

Looking North Towards The Gold Coast

There are windows all the way around the observation deck, so you can see for miles even on an overcast day like the one we had. Handily, they also offer free Wi-Fi up there, as your phone definitely won't get reception at that height, meaning you can immediately send all your photos straight to Facebook or wherever else you fancy sharing them. One of the absolute best (and slightly terrifying!) parts is the Sky Ledge. 

Looking Down 1353 Feet

These are glass box pods that stick right out of the side of the building, letting you look straight down to the pavement all those hundreds of feet below you. It's a really strange sensation stepping out onto one, and I'm not exactly brilliant with heights, but if you try to look straight ahead as you walk out

Don't Look Down

and then look down, it's not quite as bad. After a minute or two, you do actually get used to it and stop really thinking about how high you are, just focusing on taking photos like everyone else! The funny thing is, young kids don't seem to even think twice about walking straight out onto it.

So, after probably taking way too many photos from every angle possible (and yes, using one of the world's highest toilets!), it was time to head back down to street level. By then, it was getting on for about 4 pm.

Snacks And Shopping

Once we emerged from the Willis Tower, we hopped on a bus, even though it was only for one stop, just to get back across the Chicago River. We then nipped into a McDonald's to try one of their ice creams, which they'd apparently just started doing and were really nice. I also needed a coffee by then, naturally!

Thankfully The Red Line Is Below Ground

From there, it was another short bus ride of just a couple more stops to get us onto the Red Line train before the rush hour really kicked in. Jane had remembered another sporting goods shop up near Wrigley Field that I'd completely forgotten about, even though we'd passed it on the bus a few days earlier. So, the train was a good option as the shop was handily located right near the station once you got off. As it turned out, the shop seemed to stock pretty much the same stuff as the first one we'd visited near the stadium, but it was actually slightly cheaper than normal. I think we just ended up buying a couple more keyrings in there. We then walked back to the station and caught the train back towards Clark & Division, where the hotel is.

"If you don't look, then you'll never know," as they say, and seeking out that shop was a case in point! The train journey back only takes about twenty minutes and starts off above ground, running about thirty feet up between houses and over roads before dipping underground for a few miles under the city. The station we got off at was underground, but it was one of the better ones we'd seen and thankfully had a lift to get you up to street level that seemed to be kept fairly clean.

So, that was another busy day pretty much over with. I decided to call it a night relatively early, mainly because my back was honestly starting to kill me! I suppose I'm just not really used to this much walking, or maybe I'm simply getting a bit too old for it all and need to pace myself a bit better. 

It was time for the usual nightly ritual of going to the shop and deciding what to have to eat, but since we'd stuffed ourselves for most of the day, we just wanted some snacks. We ended up with a sandwich from a shop and then just lay in bed watching a baseball game that was on TV. I think it was the Washington Nationals playing, who we follow. By the time the game finished, it was around 10:30 pm, and we were both well and truly done in now, so it was definitely time for some sleep.

Reflections on the Day: Show Me the Money & Sky-High Toilets

Wednesday was one of those days where Chicago threw us a curveball right from the start. Jane’s $1000 scratch card win turned breakfast into a mission to cash in, and suddenly we were navigating federal buildings, metal detectors, and tax deductions before we’d even had coffee. Watching that tidy sum shrink to $701 after tax and fees was a reminder that Uncle Sam always gets his cut. Still, walking out with crisp $100 bills felt surreal — even if spending them turned into its own comedy routine.

The Loop gave us a mix of modern art and bureaucracy. Calder’s Flamingo looked more like a giant spider than a bird, and the post office managed to be both oversized and under-staffed. Free Sellotape was a nice touch, but the sight of armed guards and Christmas stamps from 2013 was pure absurdity. The Federal Reserve Money Museum kept the theme going: million-dollar cubes, shredded cash souvenirs, and interactive exhibits that made spotting fakes harder than expected. It was quirky, educational, and free — the trifecta of a good travel stop.

Lunch at Luke’s Italian Beef was a highlight. Pot pie pizza and giant ravioli served on prison-style plates proved that great food doesn’t need fancy surroundings. Jane’s winnings covered the bill, making it taste even better.

The Willis Tower capped the day with adrenaline and awe. Shooting up 103 floors in sixty seconds was impressive enough, but stepping onto the glass Sky Ledge was another matter. Looking straight down at the pavement from 1,353 feet was terrifying and exhilarating in equal measure. Kids ran out without hesitation, while I focused on taking photos to distract myself from the height. And yes, using one of the world’s highest toilets was a novelty worth mentioning.

By evening, snacks and baseball back at the hotel were the perfect wind-down. My back reminded me that pacing is important, but the day had been packed with surprises, laughs, and iconic sights. From lottery wins to sky-high views, Wednesday proved that Chicago can deliver both chaos and wonder in equal measure.