I decided to start our trip by overnighting in Chicago. I did not know what the weather would be like in March and didn’t want to risk any delays when flying out on the same day as our Cathay flight.

Our flight from YYZ to ORD was at 8:50pm. We reached the airport at 7pm as we knew that checking in for US flights would be a gong show. Terminal 1 is an absolute mess now which is completely dominated by Air Canada and Star Alliance. All flights for the US had to be checked in at the far left end of the check-in hall. The line for bag drop was long but moved quickly. After the bag drop line came the security line which was RIDICULOUSLY long. THANK YOU Amex Platinum card for the line bypass and we got through in 10 minutes. As we finished security, I overheard one of the security personnel saying that there was a gentleman behind me who required secondary screening – ouch. Passed through customs which took another 10 minutes and we were finally airside. Headed over to the Plaza Premium lounge which we have already been to before – nothing has changed.

After having a small meal, we got bored and left to walk to our gate. Flight was not full and began on time. Next to us was a Rouge plane bound for some beachy destination and beyond that was an AC jet with the new livery – I have to admit that seeing it in person was nice compared to seeing it on an advertisement. The design may be boring but it’s clean and crisp.

We landed in Chicago without issues and taxi-ed to a very quiet Terminal 2. Bags came out pretty quickly and we followed the signs to the free hotel shuttle stand. Waited around 10 minutes for the Sheraton O’Hare shuttle and another 10 minutes after that to get to the hotel. Had to wait 10 minutes for check in as there were 3 gentlemen ahead of me who were being helped and the agent was having a difficult time understanding them. Another agent came out and quickly helped me – I was asked if I wanted 250 points or a free beverage – beer me please! 

Got into our room, snapped pics and then walked over to the Mickey D’s across the steet. Can I tell you how good the Jalapeno McChicken was? DAMN GOOD – I wanted moar jalapenos. We hit the sack around midnight – wanted to be well rested for the 1st First class flight the next day.

Looking down right outside our room door.

Woke up the next morning to this view from our room!

Some nifty cargo jets loading and unloading.

I have to admit that this was a really nice room for an airport hotel. Compare it to the upcoming pictures of the hotel near the Hong Kong and it’s a massive difference.

Next up – Cathay Pacific First Class ORD to HKG!