Mag Mile, River walk & Millennium Park

Well, for some completely baffling reason, we were both wide awake at 6 a.m. Not even a hint of sleepiness — which frankly felt a bit rude on holiday! Instead of lying there wondering what was wrong with us, we jumped in the shower and headed straight out for a cheese grill from Dunkin’ Donuts. It’s only around the corner from the hotel, so we were there in minutes. Even at that hour, the temperature was already hovering around 25°C — a clear sign today was going to be a scorcher.

Behold, The Cheese Grill

The cheese grill has honestly become one of our absolute favourite breakfast treats in the U.S., ever since we first tried one in San Francisco earlier in the year. Seriously addictive stuff. This particular Dunkin’ had only a few seats inside, but thankfully not many people seemed keen to eat in, so we easily bagged a table. We ordered one of their breakfast deals: cheese grill, hash browns (because obviously), and a large coffee — all for $5 each. I was gobsmacked by how much food you get for so little money here. Then again, that’s America for you: stingy portions simply don’t exist.

Mag Mile

WaterTower Palace

By the time we left Dunkies it was still only about 8:30 a.m. Feeling surprisingly sprightly after our cheesy breakfast, we headed across the road to catch the number 22 bus downtown. We got off at East Chicago Avenue, walked around the corner, and hopped on the number 66 for a short ride onto Michigan Avenue — better known as the Magnificent Mile, or simply the Mag Mile.

This is the city’s main shopping hub, while The Loop is more the business centre with fewer shops. The first thing we noticed? Absolutely everything was shut. It was only 9 a.m., and clearly retail therapy doesn’t start until 10 here. With the shops firmly locked, we wandered up the road and found a little coffee shop tucked away down a side street. We ducked in for a drink to kill some time and escape the already rising temperature.

By the time we emerged, it was gone 10:30, so we strolled back down the Mag Mile towards The Loop.

Strolling The Mag Mile

My initial mission for the day was to pop into Best Buy to pick up a cheap pay-as-you-go mobile phone with some credit. My UK phone should have worked fine, but let’s just say EE aren’t exactly renowned for wizardry when it comes to roaming abroad. My plan was to get a data bundle sorted so we could use the Citymapper app properly, hoping it would help us navigate without constantly waiting for buses.

However, despite multiple attempts to buy this data bundle, the payment screen flatly refused to complete the final step. Calls and texts worked perfectly — just not the crucial data. Over in Best Buy, the cheap phones were reasonably priced, but all tied into rolling one-month contracts paid by direct debit. That knocked the idea firmly on the head.

Still, all was not lost. As in any big city, there are loads of places offering free Wi-Fi. Even if you have to stand outside pretending you’re definitely not stealing their internet, it works. In the end, that’s exactly how we managed to use the bus app for our entire stay. Not elegant, but effective.

Chocolate Heaven

We took our time soaking in the sights until we reached the Water Tower Palace — one of the few buildings to survive the Great Chicago Fire. It once pumped fresh water, but now serves as a museum for temporary exhibitions. Nothing particularly exciting was on display, but conveniently, just behind it was the Ghirardelli chocolate shop. Naturally, we had to dive in for a look (and maybe a taste or two).

These big chocolate shops are usually brilliant for finding unique goodies, though this time we only bought a couple of tins. But the unforgettable moment came on the way out. They were handing out free samples of a new product: sea salt chocolate. At first bite, it tasted like normal chocolate. Then, just as you’d walked far enough away to avoid spitting it out on their doorstep, the salt hit. Honestly, it was one of the most horrible things we’ve ever tasted. Whose bright idea was it to dump half the ocean into chocolate?

Chochy Shop

Luckily, salvation was just across the road at the Hershey’s shop. Their samples were infinitely better and helped erase the salty trauma. We spent about forty minutes mooching around, enjoying the unbeatable smell of chocolate filling the air.

From there, we wandered back down the Mag Mile, finally able to browse the shops properly. The posh handbag stores amused us most — each one displaying a single bag that probably cost thousands. We also spotted life-size model horses dotted along the street, apparently replicas of past police horses. The plan was to auction them off at the end of summer, so by now there are probably plenty of plastic horses adorning lawns, silently judging passers-by.

Lunchtime

We Were Joined For Lunch

By now, it was definitely lunchtime, and the plan was to hit up one of Chicago's supposedly best burger joints, called M-Burger on East Huron Street. Judging by the queue snaking out the door, it was clearly a popular spot – either that, or everyone in Chicago suddenly decided they needed a burger at the exact same time! I ended up spending about fifteen minutes just waiting to order, and then another twenty minutes stood around while they cooked the thing. But honestly? It was totally worth the wait. It's genuinely amazing how much food you get for your money over here. Plus, they had outside seating right there on the pavement, perfect for properly feeding your face while watching the world go by on what had turned into a seriously warm day.

Sidewalk Gardens Of Chicago

Feeling happily stuffed, it was time to move on and continue our wander down the Mag Mile. We took some time to admire all the incredible flowers they plant along the side of the road. They must spend an absolute fortune putting those in and keeping them watered – you barely see a single one out of place! And the best part? They don't seem to get wrecked or pulled up, which felt pretty impressive. After about an hour of strolling along at a relaxed pace, we eventually arrived at the Michigan Avenue Bridge, with the famous Chicago River stretching out below us.

Chicago River Walk

Chicago River Walk

Right by the bridge, they've been working on building this Riverwalk area for the last few years. It's not totally finished yet, but you can still walk a good portion of it, so we decided to drop down onto the northeast side to have a look. There are loads of places down there where you can just sit and relax, and you get some absolutely cracking views back towards the city skyline from down on the river level.

Cold Beer Time

By this point, we were both starting to feel a bit thirsty, and I'd spotted what looked like a promising pub right there on the riverbank called Lizzy McNeills Irish Bar. Naturally, we popped in for a beer. It was a surprisingly big place inside, but bizarrely, we were the only two people in there at about 2:30 pm. You'd think it would be a bit busier mid-afternoon, but the biggest surprise was actually the price – it only cost $6 (about £4) for a pint of Blue Moon beer and a coke! Apparently, they serve Blue Moon with a slice of orange, which seemed a bit odd and was definitely a first for me, but I have to admit, it did actually make it taste quite nice.

Centennial Water Arch

After about forty-five minutes spent recovering in the pub, we headed back out along the river towards the Centennial Water Arch. This thing is basically a cascading waterfall and fountain, with this massive jet of water that sprays right out from the riverbank and arches over the pathway and into the river. Apparently, it automatically stops spraying when the tour boats go past, presumably to avoid soaking everyone on deck! 

Water Arch & Police Boat Wash

A funny thing we saw, though, was when the police boat came cruising down the river – the officer clearly decided his boat needed a rinse and drove it right through the spray! There wasn't much further we could go along the Riverwalk from there because of the ongoing construction work, so we just walked back the way we came, climbed back up onto Michigan Avenue Bridge, and carried on heading south towards a place called Grant Park.

Grant Park

The Collection Of Parks

This place isn't just one park, really; it's more like a huge collection of parks all joined up, covering an absolutely massive area – something like two miles long and a mile wide. It even manages to span an eight-lane road and stretches all the way out to Lake Michigan on the far side. There's also a big open-air theatre tucked away in there, which must be great in the summer. But the absolute main thing everyone comes to see in this park is the sculpture called The Bean, officially known as Cloud Gate.

Jane And The Bean (AKA Cloud Gate)

It literally looks like a giant, highly polished stainless steel coffee bean dropped in the middle of the park. Because it's so shiny and has all these weird curved angles, you get some truly bizarre reflections, especially when you walk underneath it. Finding your own reflection when there are loads of other people around can be a real challenge, as your face appears in the most unexpected places!

Looking Into My Dreams, Awilda

Not far from The Bean, we also came across a sculpture of a massive head called Looking Into My Dreams, Awilda. I'll be honest, it looked exactly like the sort of thing that would give you nightmares; you kept half-expecting its eyes to suddenly pop open any minute!

Having decided a pub dinner was in order, we headed off the Mag Mile and down a few side streets to find Pippins Tavern. This place is honestly tucked away; it's one of those spots you'd never just stumble across, as there's not really anything else much around it. Still, the reviews I'd read online promised good food, so we figured it was worth seeking out. When we got inside, there were only a handful of other people in there, but for some inexplicable reason, the music was absolutely blasting! On the plus side though, they boasted over forty different beers on tap, and even had a waitress who brought the drinks right to your table, which felt quite fancy for what was clearly not a posh place at all.

Cooling Off In Crown Fountain

So, we settled in with a couple of drinks and then decided it was time to order some food, opting for a couple of turkey burgers. They arrived looking great and were cooked perfectly, coming with fries, a bit of salad, and even a little bag of crisps on the side.

By the time we'd finished eating, we were absolutely completely stuffed! We asked for the bill, which only came to about $24 or £17 for everything, including the beer, so we ended up leaving $30 altogether with the tip. We were really glad we'd sought this place out; it turned out to be a great find.

Looking at the time, it was already 6 o'clock, and the day seemed to have just flown by. We were both starting to feel a bit "done in" and still probably not quite adjusted to the time difference, so we decided it was probably a good idea to begin heading back towards the hotel. It was only a straightforward ten- or fifteen-minute walk from the pub over to Clark Street, where we needed to catch the bus, and it was shaping up to be a lovely warm early evening.

Back To The Hotel

"L" Train In The Loop

Luckily, we didn't have to wait too long for the number 22 bus heading back. It was only about a twenty-minute ride from where we were, so we arrived back on Division Street, near the hotel, by around 6:45 pm. Our next mission was to pop into a shop to grab some beer and snacks for the evening ahead.

By this time of day, the area around the hotel really starts to come alive. There were loads of people out and about, heading to the various bars and restaurants nearby. It was quite funny seeing this absolutely massive queue outside a new Halal Guys sandwich shop that had only just opened; there must have been easily a hundred people waiting to get in, and the queue honestly didn't seem to shrink at all during the whole two weeks we were there! After getting our supplies, we had a slow stroll back to the hotel and spent the rest of the evening watching some TV and nibbling on the snacks we'd acquired. So, that was our first full day in Chicago done and dusted. We'd pretty much managed to do everything we'd planned, and you really couldn't have asked for better weather.

All that was left to do now was get today's blog entry done. I'd planned to do it on my tablet, but it turned out the laptop I'd brought with me was much better for it. I usually take my laptop on these trips but rarely use it, if ever, so this time I was particularly glad I had it with me. It made adding photos to the blog a bit easier some of the time too. Most of the pictures I was using were on my phone, but I could transfer them from my compact camera to the phone and then add them to the blog. It sounds way more complicated than it actually is! So, after spending a couple of hours sorting all that out, it was time to finally call it a day and get some sleep, ready for another full day tomorrow. By then, it was around eleven o'clock, and I was more than ready to sink into that big comfy bed we had.

Reflections on the Day: Burgers, Beans & Boat Showers

Monday was our first full day in Chicago, and it set the tone perfectly: busy, hot, and full of surprises. Starting wide awake at 6 a.m. felt a bit unfair for a holiday, but at least it gave us time to indulge in Dunkin’s cheese grills — proof that breakfast can be both cheap and dangerously addictive.

The Mag Mile was a mix of glamour and comedy. Shops that refused to open until 10 a.m. left us loitering like eager bargain hunters, and my failed attempt to buy a pay-as-you-go phone turned into a lesson in American contracts. In the end, we became professional Wi-Fi pirates, lurking outside cafés to steal enough signal to run Citymapper. Not elegant, but effective.

Chocolate was the day’s high and low point. Ghirardelli’s sea salt chocolate was so salty it felt like chewing the Atlantic, but Hershey’s saved the day with samples that restored faith in humanity. Add in posh handbag shops displaying a single item worth thousands and plastic police horses silently judging pedestrians, and the Mag Mile delivered plenty of entertainment.

Lunch at M-Burger was worth every minute of queuing, and the Riverwalk gave us skyline views and comedy gold. Watching a police boat deliberately drive through the Centennial Water Arch spray was pure slapstick — Chicago’s version of a car wash.

Grant Park brought us face-to-face with The Bean, a shiny monument to distorted reflections, and a nightmare-inducing giant head sculpture that looked ready to blink at any moment. Dinner at Pippins Tavern rounded things off with turkey burgers, blasting music, and forty beers on tap — proof that hidden gems are worth hunting down.

By evening, the Gold Coast was buzzing, queues stretched endlessly outside Halal Guys, and we were happily stocked with snacks and beer. Blogging the day’s adventures on the laptop felt like the perfect way to capture it all before collapsing into bed.

In hindsight, Monday was a day of indulgence and discovery: food, chocolate, skyline views, and a healthy dose of humour. Chicago had already proven itself to be a city of quirks, contrasts, and unexpected laughs — and we’d only just begun.