Wrigley Field & Navy Pier

Today was scheduled for a bit more walking, so naturally, the first order of business was to get some breakfast from our go-to place, good old Dunkin' Donuts, or 'Dunkies' as they're fondly known, just around the corner. This morning's fuel-up consisted of egg and bacon on an English muffin, plus some hash browns and, of course, a large coffee to kick things off.

Wrigley Field

Its Seemed Odd Standing Here

By 9:30, we were all set to catch the number 22 bus just a block away from the hotel, heading north away from the city towards Wrigley Field. It's about a thirty-minute ride on the bus to get up there. We'd both started getting into baseball in the previous year and follow a few teams like the Washington Nationals, San Francisco Giants, and the Chicago Cubs. So, this felt like a brilliant chance to actually go and see the stadium in person – it's apparently the oldest one in the USA – and hopefully snag some game tickets for later in the week. Today wasn't actually a game day, which made it the ideal time to go and get the tickets, as we figured it would be nice and quiet.

It looks Small From The Outside

Wrigley Field opened in 1914, and its famous ivy-covered walls give it an old-world charm that is hard to beat. At the time of our visit, the stadium was undergoing a five-year, $740 million redevelopment project. In fact, the entire surrounding neighbourhood was eventually slated for revitalisation as well.

I believe the primary motivation for this is that most stadiums sit empty for about five months of the year. By incorporating more shops and restaurants into the surrounding area, the owners can generate revenue year-round through dining and special events like concerts. Unfortunately, Wrigley Field does not have a roof, and the winter weather in Chicago can be absolutely freezing.

I Often Watch Earthcam

Funnily enough, over the last year, we'd spent time watching EarthCam, which has a camera mounted on a shop across the road from the stadium. It's absolutely manic around Wrigley Field on game days when you watch the stream, so it felt really strange, and a bit surreal, to suddenly be standing right there in such an iconic spot that we'd watched so many times online.

I Wanted To Buy It All

The first thing we did was head straight into the big sports shop right opposite the stadium to see what goodies they had. I always love trying to find unique bits and pieces you can't get anywhere else, and this seemed as good a place as any to start rummaging. I probably ended up spending far too much money in there (about $75!), but honestly, I think it was all worth it. So, what did I blow my money on? I bagged myself a Wrigley Field hoodie that was half price at $35, a Cubs baseball, and some other bits and bobs like keyrings. There was honestly so much stuff in there you just wanted to buy it all and take it home with you!

While we were queuing up to pay, we had a slightly unexpected moment. The bloke in front of us reached into his back pocket to get his wallet, and he was casually carrying a gun. You immediately wonder if he's off-duty police, or then again, maybe not; it just really brought home that it seems like everyone over here is carrying one.

Got to Have My Coffee

With our bag of goodies in hand, we went across the road to the ticket office at the front of the stadium to buy our game tickets. They were $18 each, which felt pretty cheap considering the seats we got were on the lower level and not too far from the front. By then, it was about 10:30 am, so it was time for a pit stop. We headed over to McDonald's on the other side of the road for a coffee – at $2 (£1.20) for a very large one, you really can't grumble! We ended up sitting in there for about half an hour or so, just watching the world go by. 

Same Stuff, Twice The Price

Before leaving, we had a quick look in the official Cubs sports shop next door as well. It was much more expensive in there, but they did have some really nice items. We only bought a couple of bits though, given the prices.

Feeling refreshed, it was time to move on and make our way towards the lakefront walk. As luck would have it, just as we were ready to go, the bus we needed seemed to be due any minute.

Navy Pier

After leaving Wrigley Field, it was only a few stops on the 152 bus to Lake Shore Drive, which is basically the main road that runs right alongside Lake Michigan. From there, we walked round the corner to catch the 146 bus down to East Street Beach, cutting under the motorway to get there.

Lake Michigan Beach Bar

This beach is actually part of the huge Lake Michigan waterfront trail, which runs for about 40 miles, but our plan was thankfully only to walk from here to Navy Pier, which is just about a mile away. With the lovely weather we were having, the beach was fairly busy, though I imagine the water still wasn't very warm – it rarely is at the best of times! Sadly, the pub right there on the sand wasn't open yet either, so we just kept walking for about an hour along the lakefront until we finally arrived at Navy Pier.

The End Of Navy Pier

Once we got onto the pier, there honestly wasn't quite as much there as we thought there might be, but it was still definitely worth the visit, and you get some fantastic views of the city skyline from a quarter of a mile out into the lake. By then, it was definitely time for some lunch, so we grabbed a hot dog from a shop down at the far end of the pier and then had a quick look inside the large ballroom before starting to make our way back up. The odd thing about Navy Pier is that a lot of it seems to be inside or actually on the roof, so we hopped in a lift to head up to the top floor where the rather imposing 150-foot-tall Ferris wheel is located.

Up Up And Away

Ferris Wheel Of Terror

Getting on this Ferris wheel was something I just had to do, so I forked out my $8 and went for it. Like most big wheels these days, it doesn't actually stop, so you just have to time it right and step onto the gondola as it swings past, then they close a gate behind you. All was going perfectly fine until I got about halfway up and suddenly realised just how incredibly high I was, and even then, I still had another fifty feet or so left to climb! Thankfully, I wasn't completely frozen with terror, so I could still manage to take plenty of photos, and the view over the city and the lake from up there was truly was amazing. You were only actually on the ride for about ten minutes in total, which, I have to say, felt like more than enough time for me!

Amazing Views To The City

From the top of the pier, we carried on walking and went into what looked like a really big conservatory, which is called the Crystal Gardens. Inside, it's set up like a small tropical garden. I imagine in the freezing cold Chicago winters, it must be absolutely lovely to sit in here amongst the

The Crystal Gardens

palm trees when it's lashing down with rain or snowing outside. After having a wander around and admiring all the plants and the little water jets spraying over the pathways, we left via the back doors and came out onto another enclosed indoor level higher up.

Gift Shop Galore

From there, we had to go down a flight of stairs to reach the lower level, where there were loads of

Navy Pier Lower Level with Gardens Above

different shops. I was totally in my element here with all the knickknack shops! You could even build your own bear and stuff it yourself, apparently, for a price. Since we'd already done a fair bit of walking by this point in the day, I was definitely glad to find a McDonald's, so we stopped in there for half an hour or so to have a coffee and just take the weight off our feet for a bit.

By now, it was starting to get late, so we decided it was time to head outside and catch the first of two buses back towards the hotel. The area where the buses leave from at Navy Pier felt more like a full-blown depot than just a terminus, as there seemed to be about twenty different routes starting from there! I think we only had to wait about ten minutes for the number 65 bus, which took us onto the Mag Mile. Then, I had the bright idea of trying a slightly different route back to the hotel, so we decided to wait for the 36 bus instead.

All Buses Go To Navy Pier It Would Seem

This turned out not to be the best plan of the day, as we ended up waiting about twenty-five minutes for it to actually turn up. I honestly should have checked the bus times online while I still had the free Wi-Fi in McDonald's earlier, but I completely forgot! Ah well, not to worry; we weren't in any particular rush anyway, so we eventually hopped on the 36 for the twenty-minute ride. As luck would have it, this bus route dropped us off literally right outside the door of Butch McGuire's pub, so we naturally had to pop in for a swift drink!

Evening Drink

Tall Cold Beer

We didn't bother sitting inside Butch McGuire's, as it was still really warm, and they had tables out the front on the pavement. So, we happily sat there with a big beer served in a long glass. This was my first time trying Lagunitas IPA, and honestly, by golly, it was lovely when it was freezing cold. However, you definitely can't drink too many of them because they're way too strong for me, especially when they arrive in a massive 24 fl. oz. glass – that's significantly more than a standard UK pint!

While we were sitting there, we saw a woman come out of the bar across the road and promptly fall over drunk in the street. By the looks of it, she'd definitely had one too many, I reckon! But, completely undeterred, she eventually managed to get back up and just went straight back into the bar again.

Today's Must Have Item

After our swift drink, it was time to pop into CVS to grab a few bits and bobs for settling down in front of the TV that evening. Naturally, first things first was sorting out the beer supplies, and then I grabbed some flaming hot Cheetos, which I quite like. With our provisions secured, it was back to the hotel for a well-earned rest. It felt like a long day for both of us, but it had been a really good one with loads to see, do, and eat, even if we did end up spending a bit more than we'd originally planned. All that was left then was to get the laptop on and write the blog entry for the day while sipping on some cold tins of Budweiser.

Reflections on the Day: Hoodies, Hot Dogs & High Ferris Wheels

Tuesday was a day of contrasts: iconic sports history, lakefront strolls, and a few unexpected laughs. Starting with Dunkies breakfast, we were well-fuelled for the trek north to Wrigley Field. Seeing the stadium in person after months of watching EarthCam streams felt surreal — like stepping into a postcard we’d stared at from afar. The sports shop across the road was a wallet’s worst nightmare, and I happily surrendered $75 for a hoodie, baseball, and assorted trinkets. The casual gun sighting in the queue was a reminder of cultural differences we’ll never quite get used to.

Tickets secured, coffee consumed, and Cubs merchandise bagged, we headed south again towards the lakefront. The walk from East Street Beach to Navy Pier was hot but scenic, with Lake Michigan shimmering beside us. The pier itself was less bustling than expected, but the skyline views more than made up for it. Lunch was a classic Chicago hot dog, followed by my slightly nerve-wracking ride on the 150-foot Ferris wheel. Ten minutes felt like plenty when you’re dangling above the city, but the photos were worth every shaky moment.

Crystal Gardens offered a tropical oasis in the middle of the city, a place I could imagine being a lifesaver in winter. The gift shops downstairs were a knickknack paradise — from build-your-own bears to endless souvenirs — though the McDonald’s coffee break was the real highlight for our tired feet.

The journey back was less smooth. My “bright idea” to try a different bus route left us waiting twenty-five minutes, proving once again that free Wi-Fi should be used for more than checking emails. At least fate rewarded us by dropping us outside Butch McGuire’s pub, where a cold Lagunitas IPA in a comically oversized glass hit the spot. Watching a woman stumble out of a bar, fall flat, and then march straight back inside was pure Chicago street theatre.

By evening, snacks and beer from CVS completed the day. Flaming hot Cheetos, tins of Budweiser, and a laptop session to blog it all out made for the perfect wind-down. Tuesday was long, hot, and full of walking, but it delivered everything we’d hoped for: iconic sights, quirky moments, and plenty of food and drink to keep us going.

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.

Arrived

Departure

Although our flight wasn’t scheduled for an exceptionally early departure, the requirement to check in three hours beforehand meant we left home around 6:00 a.m. for our 12:20 flight, arriving at Heathrow at about 7:30. United Airlines conveniently maintains a continuously open baggage check-in, so our immediate priority was to drop off the luggage before heading to the Wetherspoon’s at the far end of the terminal for breakfast. At that hour, the pub was pleasantly uncrowded, offering ample seating and the chance to enjoy our meal while overlooking one of the runways.

Breakfast came in at around £8 — considerably more expensive than the £3 equivalent at a local spoons. But inflated pricing seems to be the airport’s favourite pastime; they’re basically money-printing machines with boarding passes. Even post-security, where VAT is no longer applicable, prices remain sky-high. Considering our last airside breakfast cost nearly £10, opting for the pre-security option seemed comparatively reasonable, especially as it included a cup of tea.

Having eaten, we headed to the security checkpoint. Knowing queues can sometimes be painfully long, we prefer to tackle this process as soon as possible. Normally, it involves the ritual of a public groping from security staff, after which there’s little else to occupy your time on that side of the barrier.

We're 12:20 Flight

With roughly two and a half hours remaining before boarding started, we mooched around the shops, bought some sweets, and settled in for a drink at the pub. This is something I always look forward to, whatever the time of day — nothing like two or three beers before take-off to put you firmly in the chill-out zone.

Given the considerable distance to our departure gate — which usually feels like walking most of the way to Chicago — we began making our way there about forty-five minutes before boarding. This proved to be a wise decision, as the walk turned out to be roughly a mile. The trek underscored the necessity of Jane’s wheelchair; without it, the journey would have taken her nearly an hour on foot.

Assistance is available, but they tend to hold you hostage so they don’t have to hunt for you later. That would mean no pub time and nothing to do. How very dare they.

Flight

Flight UA 949

The recent refit of the aircraft had resulted in an exceptionally tight arrangement of seats. Even for someone as skinny as myself, manoeuvring into the allocated space was a challenge. Matters worsened when the passenger in front of Jane reclined her seat immediately after take-off, significantly reducing Jane’s already limited space.

Ironically, whenever Jane needed to get up, she would inadvertently pull firmly on the seatback in front, waking the Italian woman, only for the seat to snap back on release. While the woman clearly disliked this, she was the only passenger in cattle class to recline — a practice most avoid given the cramped conditions.

Aside from the seating arrangement, the flight was unremarkable, save for the predictably poor quality and unpleasant odour of the in-flight meal. The seatback entertainment screens were equally disappointing: small, dim, and largely useless. Fortunately, we had brought our own tablets. By downloading the United Airlines app before departure, we were able to stream the available entertainment directly to our devices, neatly bypassing the onboard screens. The only hitch was that we had to share a pair of headphones, as the airline-provided ones were incompatible with our tablets.

O’Hare International

This flight, unlike the marathon to San Francisco, was a relatively short nine-hour hop. Aside from a bout of turbulence, everything went smoothly, and we landed at Chicago O’Hare right on schedule at about 4:30 p.m.

Immigration now resembles a supermarket self-checkout. Travellers scan their own passports, take their own photos, and provide fingerprints before a slip of paper is printed — usually bearing a likeness so dodgy it could pass for a Bigfoot sighting. Ours certainly did. This slip is then presented at a manned desk for a quick verification before you’re allowed to proceed to baggage claim.

Once reunited with our luggage, we passed through customs and headed out to find the airport’s internal transport system. Inconveniently, it doesn’t directly connect with the CTA (Chicago Transit Authority) train line into the city centre — at least not from this terminal. We knew this in advance, but still…

Navigating the connection to the CTA proved to be the trickiest part of our arrival. Following a poorly signposted route, we embarked on what felt like a three-mile hike through car parks (maybe we took a wrong turn, hard to say), tunnels, and a series of lifts before finally reaching the CTA Blue Line station. This was the first of two trains we’d need to reach our hotel.

Given the CTA’s colourful history of operational mishaps, I’d invested a not-insignificant amount of brainpower in plotting our route. As it turned out, my meticulous planning was entirely justified. The airport’s train station was still plastered with “under repair” signs after a rather dramatic incident the previous year. A driver had apparently enjoyed a little too much shut-eye on approach, resulting in her train climbing the station stairs and escalator before parking itself neatly on the mezzanine level. One can only imagine the commuters’ surprise. Thankfully, it all happened in the wee hours, so the audience was minimal.

Mercifully, the potential for a human bowling tournament was avoided. Rumour had it the security camera footage was pure comedy gold. One anecdote described a transit police officer mid-conversation with a passenger, only for their chat to be cut short by the distant rumble and sudden vertical ascent of a rogue train. The footage reportedly captured both individuals bolting in opposite directions in perfect synchrony. Miraculously, despite the chaos, no one was hurt. You’ve got to admire that level of slapstick without casualties.

Travel To The Hotel

Next up: Ventra Cards. These give unlimited travel on all CTA buses and trains for a week. They’re bought from machines at the station and work much like Oyster Cards back home — tap once for buses and L trains, or tap in and out on Metra commuter rail, which charges by distance.

A seven-day unlimited pass costs $28, plus a one-time $5 fee for the card itself. The good news is that the $5 is credited back for future use.

Side note: the L trains and subway are essentially the same thing. The “L” stands for “elevated,” referring to the raised tracks they mostly run on, though the Red and Blue Lines dive underground through parts of the city.

After a bit of faffing about — and some help from a lovely woman at the barrier — we got our cards sorted. If you’ve read previous journals, you’ll know ticket “vendy-bots” are part of a global conspiracy to make our lives difficult. Once armed with the card, though, it’s simple: tap the reader, barrier opens, off you go.

Over the next couple of weeks, I realised paying cash actually costs more. No wonder I only saw two people use cash on a bus during our entire stay. Train tickets bought with cash also carry an extra 50¢ surcharge.

Trains run every ten minutes, so there’s never a long wait. We hopped on one for the 45-minute ride into The Loop — Chicago’s city centre. Annoyingly, the station where we’d planned to change trains had no lift and far too many stairs, which wasn’t going to work with luggage. So we stayed on for one more stop, where a lift was available. Unfortunately, the lift smelled strongly of pee, as many seemed to double as public conveniences. We held our breath and pressed on.

From there, we switched to the Red Line heading for Clark & Division station. It was only a short walk to our hotel on North Dearborn Street. Thanks to Google Street View, I already knew the route and direction. About ten minutes later, we arrived. By now it was roughly 6 p.m. local time — six hours behind the UK — though oddly it didn’t feel like midnight at all.

Hotel & First Night

Not The Biggest TV Screen

The Hotel Indigo sits in Chicago’s Gold Coast area, a couple of miles north of the city centre. It felt like a charming neighbourhood, almost its own little town, with pubs, bars, shops, and supermarkets nearby. The hotel itself was tucked up a side street. I think it had fourteen floors, and we ended up on the twelfth. Normally you pay extra for a higher floor to avoid traffic noise, but this was just a standard room — perhaps we got lucky. The view wasn’t anything special, but the peace and quiet were welcome.

The room was lovely: a desk, a shower with excellent water pressure, and walls painted in quirky, colourful shades, just like the rest of the hotel. It gave the place a lively, cheerful feel. We were glad we’d picked it — it was actually one of the first options I’d found online.

Nice View of the Supermart Roof

By 7:30 p.m., we were ready to grab food and supplies. We strolled down to Walgreens on the corner. The evening was still warm — around 30°C — so progress was slow. We popped into Dunkin’ Donuts en route, but their ovens were off, so no luck there. Instead, we picked up sandwiches at Walgreens, then crossed to CVS for beer (since Walgreens doesn’t usually sell alcohol).

Back at the hotel, we tucked into our haul with a much-needed cold beer. Shame there wasn’t a fridge in the room, especially given the heat, but the air-conditioning was excellent — quiet and efficient. There was even a safe in the wardrobe. The only oddity was the lack of drawers, but that’s easy enough to live without for a couple of weeks.

By 9 p.m., I decided to start my blog and posted the first entry online for anyone who wanted to read it the next morning. It was my first time blogging “on the fly,” rather than relying on photos and notes after the trip. With that done, it was finally time to curl up in bed.

Reflections on Sunday: Bigfoot At Immigration

Looking back, Sunday was one of those marathon travel days that somehow managed to feel both exhausting and oddly satisfying. The early start at Heathrow reminded me that airports are less about travel and more about testing your patience — inflated breakfast prices, security rituals, and the long trek to the gate that felt like a warm-up for Chicago itself. Jane’s wheelchair proved invaluable right from the start; without it, that mile-long walk would have been a trial before the trial.

The flight itself was cramped, predictable, and faintly ridiculous. Airline seating seems designed to remind you that personal space is a luxury, and Jane’s battle with the reclining Italian woman was a comedy sketch in its own right. At least our tablets saved us from the indignity of squinting at those useless seatback screens. Sharing headphones wasn’t ideal, but it did add a touch of teamwork to the entertainment.

Arrival at O’Hare was a mix of modern efficiency and absurdity. The new immigration kiosks felt like self-checkouts gone rogue, producing mugshots that looked more like cryptid sightings than human likenesses. The trek to the CTA station was another endurance test — tunnels, lifts, car parks, and signage that seemed designed to confuse rather than guide. Accessibility was patchy at best, with lifts that doubled as public conveniences and stairs appearing at the worst possible moments. Still, the Ventra card system was a win: simple, affordable, and far more inclusive than many cities we’ve visited.

By the time we reached the hotel, the Gold Coast neighbourhood felt like a reward in itself. The Indigo was colourful, quirky, and mercifully quiet — a welcome contrast to the chaos of travel. The evening stroll for supplies was slow thanks to the heat, but it gave us our first taste of Chicago’s summer nights. Sandwiches, beer, and air-conditioning became the perfect end to a long day.

In hindsight, Sunday was less about sightseeing and more about survival — navigating airports, airlines, and transit systems with humour and resilience. It set the tone for the trip: challenges would come, but with planning, patience, and a bit of laughter, we’d find our way through.