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 Even post-security, where VAT is no longer applicable, prices remain sky-high.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.