Oak Street Beach & The Mag Mile

Today was our last full day here in the Windy City. The temperature, like the humidity, had actually gone down by quite a lot today, which was a relief, but it was still lovely and pleasant. So, we thought we would start by walking up the road to Oak Street Beach, which is only

Oak Street Beach

about a fifteen-minute stroll from the hotel. There were already plenty of people out enjoying the beach when we got there, although I wasn't too sure how warm the water itself was in the lake! Looking back from the beach into the city, most of the tops of the tall buildings were covered in cloud at the moment, which seemed to be swirling around them quite dramatically.

Mag Mile Mooch

To Early For The Beach Bar

After sitting in the beach area for about forty-five minutes, we walked down a little bit further along the lakefront but couldn't really be bothered going into the bar right there on the beach – shame that was, it looked quite nice. So, we cut back under the motorway and got back onto the top end of the Magnificent Mile, where we went for a coffee. Even though we'd been along this stretch of road before, we hadn't actually ventured inside the many shopping centres that line it.

The first one we decided to explore had security guards who looked exactly like Canadian Mounties in their uniforms, which was a bit unexpected! One thing that really bugged me about this particular place, though, was that if you tried to go in the main entrance, you either had to walk up a whole load of stairs or use the escalator, neither of which was any good for Jane at all.

Because of the lack of accessible entry, we had to come back out again and go around the corner into Macy's instead, just to use the lift in there to get inside. Once inside, it was quite good having a look in the Lego shop at all the amazing things they had made out of bricks.

The 900 mall

After that, it was time for another cup of coffee before we headed back out and crossed the road to another shopping mall called '900 Shops'. Don't be fooled by the name – there definitely aren't 900 shops in here; it's just called that because of its address. They even had a Christmas shop that's open all year round, which was a bit odd in September! This place was very upmarket though, which probably explains why there was hardly anybody else in it.

Fourth Presbyterian Church

From there, we went next door to the Fourth Presbyterian Church. It looks quite odd nestled in amongst all these towering tall buildings, almost looking small and tucked away from the outside. But once you step inside, it's surprisingly big and feels incredibly grand. I think it's one of the most impressive buildings in this whole area.

After spending some time looking around in the church, we walked for a bit, just looking at more of the very high-end shops – you know, the sort with literally just 'one handbag in the window'! We then got on the bus heading down the Mag Mile and over the Michigan Avenue Bridge to visit a couple of the more high-end gift shops.

'Bye-Bye Chicago' is one of the best ones along there; they have loads of unique things you don't normally see in other shops. However, as you'd expect, they definitely come at a price! I can't even remember exactly what I bought now, to be honest, but I know I've got them all safely in a box at home somewhere!

Chilling Around the River

After grabbing a sandwich from the shop, we caught the bus back over the bridge. Even though it was only just one stop, it took us right to where there was a pop-up market going on, which was handy. There are loads of places to sit around here and just soak up the atmosphere, and you get a wonderful view of the iconic Wrigley Building from this spot, which is where the chewing gum originally came from, apparently.

One Of Many Pocket Parks

WGN Radio also has its offices right here on the bottom floor corner of one of the buildings, so you can actually see right into the studio while they are on air broadcasting, which is quite interesting to see. There was one of the stalls at the pop-up market that was giving away free tote bags with a choice of different logos on them, so Jane patiently queued up to get one of those. After that, we just had a casual walk around the plaza area here for a bit.

Free Tote Bag

It was time for something else to eat now (always hungry!), so we got back on the bus and travelled up the road for about half a mile or so. We then cut through some side streets and went into McDonald's for a burger. They do this rather odd thing where they offer a cheeseburger meal, but you actually get two double cheeseburgers with it – I'm not sure why, but there you go!

Bus Ride Rage

From there, we cut through even more side streets until we came out onto North Clark Street and managed to catch the number 22 bus back towards the hotel. We almost missed it, but thankfully, the driver waited for us, which was good of her. Once onboard, there was this really annoying old bloke sitting near the front, talking incredibly loudly on his phone. To make it even worse, he sounded exactly like Elmer Fudd from the cartoons, which was just grating.

After we had gone a couple of stops, the driver then waited for a woman who was running for the bus with a kid in a pushchair. As soon as she got on board, as kids often do, the little one started crying really loudly. So now you had a screaming kid adding to the noise, and this bloke still shouting down his phone because the person on the other end clearly couldn't hear him anymore over the din.

He then, rather foolishly, started having an argument with the mother of the kid, actually telling her to "shut it up," which was definitely the wrong thing to say in that situation! She immediately started shouting back at him in a voice that sounded like Big Momma from the movie. To me anyway, some of the locals here sound like they could be from Texas when they talk, but you are in the Midwest, so you can probably imagine what it was like.

Personally, I'd much rather listen to a screaming kid any day than someone shouting down a phone like that. In the end, the bloke gave up on his phone call but certainly not on the argument. He actually said to her, "I hate screaming kids," and she instantly shot back, "So you hate my baby!" And thus it continued back and forth; they were still trading remarks and insults when we got off the bus further up the road. Honestly, after all that commotion, I was half-surprised that nobody ended up getting shot, as they do seem to be a bit trigger-happy around here!

Last Evening Stroll

After that eventful bus journey, it was just a short walk back to the hotel to start packing some things up ready for the morning. By about 7 pm, though, we thought we'd head back out for a last walk around the shops just down the road near the hotel. This area was really starting to get properly busy by now. Not only was it Friday night, but it was also the start of the Labour Day weekend, with Labour Day itself being on the Monday, and thousands of people tend to head into cities like Chicago for it.

It's also, rather grimly, apparently when gun crime starts to pick up around here. I remember reading that at the same time last year, a shocking nineteen people were shot and killed in the city over that three-day Labour Day weekend. It's a pretty sobering thought when you're walking around.

Anyway, trying not to dwell on that, we dropped into Walgreen's for a last look around. And, as luck would have it, we found a couple of those classic USA flags that you always see everybody waving on TV. At just 99 cents each, we absolutely had to buy them! The slightly annoying thing was that we then had to walk all the way back up the street again specifically to buy a cardboard tube to put them in, just to make sure the sticks they're attached to wouldn't get broken or snapped on the flight home.

We then took a leisurely stroll back towards the hotel on what was still a warm and busy summer evening. The cicada bugs weren't making anywhere near as much noise now that it had almost gone dark, plus I think their noisy three-week cycle in the trees was starting to come to an end anyway.

All in all, I think this had been a really good holiday. We couldn't honestly have wished for better weather than we had had for the majority of it. It was time now to get back to the serious business of doing some more packing. It turned out we had bought more bits and pieces than we originally thought we had, plus the two hoodies that I got took up a fair bit of room in the bags. It was a bit of a squeeze getting it all in, to be honest!

We even ended up having to dump the bottle of shampoo and the soap that we had bought just to make space. On top of getting everything to fit, we also had to constantly think about how much weight was in each bag, because if you go over 24 kg, they charge you extra for it, and that certainly isn't cheap!

Reflections On The Day: Beaches, Bickering & the Bittersweet Last‑Day Shuffle

Friday had that unmistakable “last full day of the holiday” feeling — a mix of wanting to squeeze in just a bit more exploring, while also realising your legs, your bags, and your energy levels are all very much ready for home. The drop in temperature was a blessing, and Oak Street Beach was the perfect gentle start. There’s something magical about standing on warm sand with skyscrapers looming behind you, their tops swallowed by swirling cloud. Chicago does dramatic weather better than most cities.

The wander back onto the Magnificent Mile felt like a victory lap. You’d walked this stretch plenty of times, but dipping into the shopping centres gave it a fresh twist — even if the accessibility situation left a lot to be desired. The Mountie‑lookalike security guards were an unexpected bonus, and the Lego shop was a fun little detour. The “900 Shops” mall, with its year‑round Christmas store, was peak Chicago eccentricity. And the Fourth Presbyterian Church, tucked between glass towers like a Victorian time capsule, was a reminder that even in the most modern cities, history still finds a way to stand its ground.

The afternoon around the river had that lovely, relaxed last‑day vibe. A sandwich, a pop‑up market, a free tote bag, and the Wrigley Building gleaming across the water — simple pleasures, but exactly the kind that stick with you. Watching the WGN Radio studio through the window felt like peeking behind the curtain of American media, and the whole plaza had that easy, summery buzz.

Then came the bus ride. Of course it did. Chicago wasn’t going to let you leave without one last slice of public‑transport chaos. Between Elmer Fudd shouting down his phone, the crying toddler, and the mother who absolutely was not going to be told to “shut it up,” the whole thing descended into a full‑blown soap opera on wheels. You could practically hear the theme tune. It was chaotic, loud, and mildly terrifying — but also very, very Chicago. And the fact that nobody got shot felt like a small miracle.

The evening stroll was the perfect way to round things off. The city buzzing with Labour Day weekend energy, the slight edge of danger in the air, the last‑minute impulse buys at Walgreen’s, and the triumphant acquisition of two classic American flags — all very end‑of‑holiday behaviour. The cardboard‑tube mission was peak practicality, and the cicadas winding down for the season added a strangely poetic touch.

Back at the hotel, the reality of packing hit hard. Souvenirs multiply when you’re not looking, hoodies expand to twice their size, and suddenly you’re playing luggage Tetris while muttering about weight limits and airport fees. Dumping the shampoo and soap felt like a necessary sacrifice to the travel gods.

But underneath all that, there was a quiet satisfaction. You’d had brilliant weather, seen everything you wanted to see, eaten well, explored widely, and experienced the city far beyond the tourist façade. You’d wandered beaches, parks, neighbourhoods, and shopping districts; you’d seen art, architecture, baseball, fireworks, fountains, and the odd argument on public transport. You’d lived Chicago, not just visited it.

Friday wrapped the whole trip up perfectly — warm, lively, a bit chaotic, and full of character. A fitting end to a holiday that had been exactly the same.