The Windy City

Introduction and Planning

Late last year I was chatting with my friend Will about his recent move from London to Chicago. He was saying how much he loved the city and how great the view from his apartment was.

Around the same time BA were running a premium class travel sale and with World Traveller Plus tickets available for a pretty reasonable price so I was very tempted to book and upgrade to Club World (25,000 miles for the return).
I had planned to visit in February but Will warned me about the snow that ended up being over 4 feet deep! April seemed like a more sensible plan and so we looked into the dates.
After thinking about the trip for a while I thought how great it would be to travel in First Class on the outbound leg. I priced up a trip in Club World with an outbound upgrade (25,000 miles for the leg) and while it was quite a bit more expensive I figured that the upgrade was worth it. I also considered upgrading the return but I found that this wasn’t possible as the return flight that I wanted was a 3-class with no First section.
With everything booked I once again turned my mind to how to get to Heathrow. After my positive experience with the Terminal 5 business car park (see my Munich Trip Report) I decided to try their short-stay offering. £77 for 4 days parking is quite steep but it is just yards from the terminal and is covered from the weather.
LHR – ORD, British Airways 295, First Class
I left home at around 7am and made it to Heathrow around 8:30am. I was able to park really close to the South Entrance and so it was just a short walk to the First check-in area.
At the entrance desk I was asked at what time my flight departed. I replied that it was 11:45 and to my shock I discovered that all flights past 11:30 were to be cancelled! As we now know the cloud of volcanic dust from Eyjafjallajokull had closed UK airspace. I was directed to the Club World check-in desks and after a quick call to Will (waking him at 3am) I was rebooked for the following day.
The next day all flights were still grounded. At 06:30 I called the BA Gold line and rebooked for two weeks later.
LHR – ORD, British Airways 295, First Class, second attempt
Annoyingly my expensive parking space from my previous attempt to travel cost me £77 for around 15 minutes. Fortunately it looked like my insurance would cover this cost so I re-booked another short-stay parking space.
I also noticed that my new return flight was a 4 class 777 and so knowing that there was at least one 777 flying with the new First cabin I cashed in a further 25,000 miles and upgraded my return flight.
There was a short queue to check in, while I waited I chatted to the receptionist who said that most of the problems caused by the ash had been resolved and that customers had been very understanding.
After check-in in I headed for the security line which, (as always) was no faster than the ordinary line.
Once past security I turned right and into the Concorde room for breakfast. The service was very prompt and attentive and I had a very tasty full English breakfast.
I then booked a massage at the Spa before heading to the shops to buy a gift for my hosts.
By the time I returned to the lounge I noticed that my flight had been assigned a gate – the dreaded A10 bus gate. I can appreciate that bussing will happen until the C terminal opens but it always puts a dampener on the First Class experience.
Fortunately the drive was short and I was soon up the steps and into the nose of the 747 that would be my home for the next 8 hours.
The on-board service was fine (if not spectacular) and I enjoyed a 3 course lunch over “Up in the Air“. After that I slept for a couple of hours, waking up in time for the afternoon tea service. Apparently this is now in association with The Dorchester but I couldn’t see any tangible difference to the usual service.
One other change to F was the in-flight amenity kit. This new design from Anya Hindmarch comes in a semi-ridged case and I think it’s a big improvement over the old boxes.
On landing at Chicago I was feeling a bit dehydrated and so I took a bottle of water with me. This turned out to be a very wise decision as the immigration line was VERY long and the air-conditioning was not up to the job. After queuing for 90 minutes I was eventually through to baggage claim.
The terminal transit train was easy to find and I made my way to terminal 2 to find the CTA train into the city. I purchased a 3-day pass for a very reasonable $14 and boarded the train.
The train stopped about 10 times before I reached Clark/Lake where I disembarked and headed to ground level to meet Will.
Chicago Highlights
We had a packed few days that I’ll condense into the highlights.
  • The first night we went for an excellent dinner at Thai/Sushi bar ‘Ma and I‘.
  • We then took a walking tour including the ‚ÄòThe Bean‚Äô, the ‚ÄòJay Pritzker Pavillion‚Äô and the ‚ÄòTribune Tower‚Äô (which includes stone from a huge variety of famous buildings including the Pyramids, Notra Dame and Westminster Abbey).


  • In the afternoon we enjoyed the very entertaining ‚ÄòUntouchables Gangster Tour‚Äô . This was a good fun and educational tour covering the various gangs, Al Capone and the Valentine‚Äôs Day Massacre.
  • For dinner we secured a table at the Purple Pig which serves an excellent selection of ‚ÄúCheese, Swine and Wine‚Äù. The sommelier recommended a Greek Viognier, we were sceptical but it turned out to be pretty decent.
  • That evening we headed out to a variety of bars including ‘The Violet Hour‚Äô which has a very non-descript facia (it looks like a wooden hoarding covering some construction work) and some interesting house-rules including ‚ÄòNo O-Bombs‚Äô (whatever that is), ‚ÄòNo Jager-bombs‚Äô (again, not sure on that one), ‚ÄòNo Budweiser, No Light Beer, No Grey Goose and No Cosmopolitans‚Äô (which all sounds fair enough).
  • The next day we checked out the ‚ÄòChicago Institute of Art‚Äô which included a Matisse exhibition (I‚Äôm not a big fan).
  • We then took in the very interesting Architectural Boat Tour which I’d class as ‘not to be missed’ given the huge variety of architecture that Chicago has to offer.
  • That evening I experienced a real Chicago Pizza at Giordanos, this was quite an experience. Each pizza takes about 45 minutes to cook and is an incredible 3 inches deep! We had a 12 inch pizza between 3 and there was plenty left over. Highly recommended!
  • On my last day we met one of Will‚Äôs friends for a tour of the excellent Shedd Aquarium the exhibits were excellent as was the 4D cinema. The live ‚ÄòFantasea‚Äô [sic] show was a bit disappointing as it erred on the side of fantasy rather than educational value.
  • It was a beautiful day so we wanted to get up one of the city‚Äôs towers. The main options are the Sears/Willis Tower (it was renamed in 2009) where the Skydeck costs $16 or the John Hancock Centre where the 95th floor observation deck which costs $20. However we discovered that there is a bar on the 96th floor of the John Hancock Centre which just asks that you buy a drink! Why you‚Äôd pay $20 to get into the observation deck I have no idea. We enjoyed a couple of beers and some snacks while enjoying the amazing views.
ORD-LHR, British Airways 296, First Class
As we headed back to Will’s apartment I found out that the volcanic dust cloud had closed airspace over Ireland and Scotland and so I became worried that my flight would be delayed.
Fortunately all was well and I was able to check in without any problems.
The lounge at O’Hare includes a First Class dining room where I enjoyed some excellent fish-cakes and a slice of cheese cake. Afterwards I headed to the lounge and was disappointed at the lack of a First Class section.
Only once the flight was called did I leave the lounge and discover a separate First lounge across the hall!
Priority boarding worked well and I was soon settling in 1A. Unfortunately the cabin hadn’t been updated to the new First but I was planning to sleep so it wasn’t a problem. I enjoyed a hot-chocolate and some biscuits before sleeping for 6 hours.
We landed perfectly on time and taxied up to…. Another remote gate! After another annoying bus ride I was quickly through immigration. My bag was through within about 10 minutes and I headed out and up the lift to the arrivals lounge.
Here I enjoyed another Concorde room breakfast (again, very tasty) before heading across the bridge to my car and then back home.

This was an excellent trip, I loved Chicago and would love to return. The city seems very clean and tidy, has some great architecture and being next to the lake it’s very picturesque.


I’d love to go back and spend some time on the lake. I’d also like to see it in the winter.
So if you’re planning a trip to the US and you’re not sure where to go I highly recommend considering a trip to the Windy City!