Lake Michigan Waterfront walk

We started the day by catching the Red Line train downtown to the lower part of The Loop, and then we hopped on the same bus we'd used before that heads towards the aquarium area. This time, instead of turning into Grant Park, we decided to take a walk along the shore of Lake Michigan. It turned out there was a triathlon underway, so there were hundreds of runners filling up the usual upper pathways.

Lake Michigan Wander

Lake Michigan & The City

The paths right along the lake are actually sloped. This is a clever design so that when water splashes up onto them on windy days, it just flows back into the lake. However, it's not so great when you're trying to push a wheelchair, as you're constantly being pulled downhill towards the water's edge! Trying to counteract that pull made it really difficult to push in a straight line, which was exactly why I'd planned on sticking to the upper pathways in the first place. Although this spot is normally quite peaceful and open, having the triathlon on definitely made the area noticeably much busier.

Jihn Hancock Building In The Clouds

Despite the unexpected challenges with the path, it was still lovely just to stroll along by the lake. You get a fantastic view of the city buildings from down there, and it was quite cool watching the clouds drift between the tall buildings in the city – one minute you'd see them clearly, and the next they'd disappeared right into a cloud! The sun was out though, and it had become another hot day. After walking for about an hour and a half, we came across a kiosk selling hot pies and coffee. We stopped there and had a couple of chicken pies and a drink whilst watching the various boats out on Lake Michigan.

Millennium Park Meander

After grabbing something to eat, we headed across towards the very north end of Millennium Park. That involved crossing a pretty daunting ten-lane road, which is definitely not the easiest thing to get across in the short amount of time you're given at the crossing, but thankfully, we made it without getting squashed! This particular part of the park is quite new, only having been completed in the last few years.

The Hot Curly BP Bridge

One of the main features here is the BP Bridge, which impressively spans over another eight-lane road. This bridge is entirely made out of stainless steel, and it shines incredibly brightly on a sunny day like today – though it does mean it gets pretty hot to the touch as well! It's not a straight bridge at all; it sort of curls around and doubles back on itself before actually crossing the road, and then does the same wiggly bit on the other side to bring you back into another section of the park.

The Harris Theatre

From the bridge area, you come across the Harris Theatre, which is a large outdoor auditorium. I initially guessed it must hold around 1,000 seats, but I later found out it actually holds 1,500 people. Given how harsh the winters are here, you can just imagine that it doesn't get a whole lot of use during certain times of the year, although they do have an indoor part on the opposite side of the building, I think. Just a short walk further on from there, and you're essentially right there on Michigan Avenue, with all those glorious shops!

Before hitting the shops or anything though, we stopped to look at an open-air photography display that was set up on the edge of the park. They had enlarged people's photos to a massive size and put them on these big billboards that you could walk all around. All the pictures had been taken within the park itself by either locals or visitors, and it was nice to see that none of them had been damaged despite being out in the open for a few months.

Chicago River Walk

Right then, it was back onto the Mag Mile we went, heading north once more. We stopped off at CVS for a couple of cold drinks, as the temperature was really starting to climb again now. It was actually quite nice sitting in this small plaza we found nearby, even though it was right next to a busy road, just chilling out in the warm weather for a bit. Just up the road from here, you come back onto the Chicago River. We decided to drop down onto the opposite side of the river to the other day and seek out the McCormick Bridgehouse Museum. Handily, it's free on a Sunday, plus I hadn't been able to find it the other day because I'd been on the wrong side of the road!

Bridge Lifting Gear

It's only a small museum, as you'd expect, but it's built inside one of the actual bridge lifting houses, in one of the bridges that they still raise once or twice a week. You can even go right through to see where the huge lifting gears are that raises the bridge and peer at all the massive cogs that make it work. They even sell special tickets to come down here specifically to see them all turning while the bridge is being lifted, but today wasn't one of those days for a bridge lift, unfortunately. Some of these lifting bridges also carry trains, so you can just imagine the amount of chaos it causes with both the road traffic and the trains whenever they do lift them!

The museum is spread over five floors, and each floor is only tiny, but it gives you a fascinating history of how the Chicago River came to be and how they famously raised the entire city more than thirty feet above it back in the day. It's quite strange seeing roads that are completely underneath buildings – it's like a whole underground city down there! Most of it seems to be used for deliveries and loading for the shops and offices above, and it doesn't look like the sort of place you'd particularly want to be at night, to be honest.

Michigan Av Lifting Bridge

One of the most amazing things they explained is how they managed to reverse the flow of the river. It used to flow into Lake Michigan, but they reversed it using a lock system in a huge effort to clean up the lake, which is actually where all the drinking water for the city comes from. When you reach the very top floor, you're about twenty-five feet above street level and get a cracking view looking along the river and Michigan Avenue. Unfortunately, Jane couldn't manage the stairs all the way up, so she stayed down at the bottom. They do have computers down there that give you a virtual tour of all the upper floors though, which is a really good idea, as it's not like they could possibly squeeze a lift into that tiny space anywhere!

Sadly Not An Accessible Museum

I think we spent about an hour in there altogether, and then we had a walk along the south side of the river. Sadly, there don't seem to be any pubs on that side, which was a bit of a disappointment! You could, however, hire these four-wheeled pedal bikes, but we decided to give that a miss when we saw how much they were charging for just four hours. So, we ended up backtracking the way we had come and climbing back up to the main road.

Lots Of buses On The Mag Mile

By now, we were both really starting to suffer in the heat again, and it was getting on for about 5 pm, so we decided to call it a day and head back. Not that the shops shut here on a Sunday evening or any other day for that matter, they seem to be open constantly! We hopped onto one of the many buses that would take us back up towards the very top of the Mag Mile and then it was just a short walk through the side streets back to the hotel. In hindsight, it probably would have been a better idea to get the train, as the traffic was an absolute nightmare on the bus route, but that would have meant having to walk about four blocks from the station, and that was definitely not something we wanted to do in the city in that heat.

It was honestly lovely to get back into the hotel room with the air conditioning blasting and immediately have a shower, because everything seemed to have well and truly stuck to me by then!

Dinner Plans

By about 7:30 pm, we were both absolutely starving, so we decided to walk round to Mr. Gyro's, a place that apparently does a fantastic range of burgers at really low prices. It looks a bit of a dump from the outside, I have to say, but with so many takeaways crowded around here, you figure it must be good to survive. And I must say, this turned out to be one of the best burgers I'd had in a long time! They had a deal on for two burger meals for the low price of only $12, which was definitely well worth it.

Just before we went there, we'd actually nipped into Plum Market on the way past to grab some bananas. We honestly couldn't believe it when we found out they tax you 3 cents on fruit, but not on the takeaway junk food we were about to buy! So much for trying to encourage people to eat healthily, eh? Nobody seems to be able to work out how the tax system works here at all; I reckon the mayor just makes it up as he goes along, depending on how skint they are that week.

Anyway, back to the food – thankfully, we made sure we got two sets of knives and forks this time so we could both properly dig in! Not sure how we only ended up with one set last time, but they literally hand them out at the checkout with almost anything you buy, even if it's just a yoghurt, if they don't see you've already got some, you'll have them now. Most of the time now, we just wash and save them, as they're normally good quality disposable stuff they give you.

At least we had a desk to eat from back in the hotel room, although we only had one chair. The solution? I used Jane's wheelchair to sit in while she took the proper chair. Very comfy indeed it was, actually!

Evening Stroll

So, by now, I was starting to run low on beer again and figured it was a good time to pop out to the shop. Plus, I really wanted to check if the Ventra card had actually worked properly when we topped it up earlier with another seven days of travel. 

Just before we went to Mr. Gyro's for dinner, I'd ducked into a subway station nearby to add more credit to the Ventra cards. You're meant to do it by simply tapping the card on the machine and then selecting what you want on the screen. As soon as you put the $28 on, I thought it should work instantly, right? What I didn't realise is, unlike Oyster cards back home that store the credit directly onto the card straight away after you top up, here you have to wait a few minutes for the payment to spread out to the terminals and become valid. Naturally, that completely confused me, and I honestly thought I'd messed it up.

Anyhow, as I was out on my own anyway, I decided I'd just go one stop on the subway and then come straight back again just to test it out. Apart from having to touch the card on twice at first (which made me panic briefly!), it all worked fine. So, after that successful five-minute ride on the subway, I decided I'd walk up towards the Oak Street Beach area for a bit, even though it was dark by now.

Careful Where You Walk

This is the area where the famous Drake Hotel is all lit up at night, which looks great. But you soon realise that this is definitely not one of the safest areas to be walking around in after dark. There were just far too many shifty-looking people hanging about. Because of that, there was absolutely no chance I was going to risk using the underpass to get across to the beach side of the road. It really did feel quite unsettling, like there were eyes watching you that you couldn't quite see, or maybe even somebody waiting to pounce.

Because of how it felt, I quickly decided that discretion was definitely the better part of valour, and I shot off round some side streets to get back to where there were more people who, crucially, didn't look like they wanted to rob me! Thankfully, getting back to a more populated and safer-feeling area was only about a five-minute walk, or perhaps even a bit of a trot, from where I was.

By the time I'd navigated my way back and headed over to CVS for my beer for the evening, it was almost 9 pm, I think. I was back at the hotel for about 10 pm. Just enough time left to quickly write up the blog for the day and then head to bed. It had definitely been a long day, with a lot of walking in that hot weather, but looking back, it was worth every step.

Reflections On The Day: Slopes, Steel & Shifty Streets

Sunday was one of those days that looked simple on paper but turned out to be full of surprises — some lovely, some sweaty, and one or two that made the hairs on the back of your neck stand up. The walk along Lake Michigan was beautiful, even if the sloped paths tried their best to drag Jane straight into the water. Between the triathlon crowds, the heat, and the constant sideways pull of the wheelchair, it felt like we were doing some sort of endurance challenge of our own. Still, the views of the skyline, the drifting clouds, and the boats on the lake made it worth every awkward shove.

Crossing a ten‑lane road to reach Millennium Park felt like a real-life game of Frogger, but once we made it across, the BP Bridge and the newer parts of the park were a joy to wander through. The stainless-steel curves of the bridge gleaming in the sun, the outdoor theatre, the photography displays — it all had that classic Chicago mix of art, architecture, and a bit of showmanship.

The McCormick Bridgehouse Museum was a brilliant little find. There’s something oddly satisfying about seeing the guts of a working bridge — all those gears, cogs, and mechanisms that quietly keep the city moving. Learning how Chicago raised itself thirty feet and even reversed the flow of its river was one of those “only in Chicago” moments. It’s a city that doesn’t just solve problems; it rewrites the rules entirely.

By late afternoon, though, the heat was becoming unbearable. The bus ride back was slow, sticky, and full of people who looked just as melted as we felt. Getting back to the hotel and stepping into the air‑conditioning felt like entering heaven.

Dinner at Mr. Gyro’s was a revelation — proof that the best food often comes from places that look like they should have been condemned in the 90s. Two burger meals for $12 and absolutely delicious. Meanwhile, Plum Market taxed the bananas but not the junk food, which summed up American logic perfectly.

The evening stroll was… memorable. Testing the Ventra card was fine, but the walk near Oak Street Beach after dark was a reminder that even the nicest cities have corners you don’t linger in. The Drake Hotel looked gorgeous lit up, but the atmosphere around it was decidedly less charming. Trusting your instincts and making a tactical retreat was definitely the right call.

Back at the hotel, beer in hand and blog written, the day felt full and satisfying. It had been hot, busy, and occasionally tense, but also scenic, interesting, and full of those little moments that make a trip feel real. Sunday was Chicago in a nutshell: beautiful, unpredictable, and always keeping you on your toes.