This past weekend I finally had the pleasure of visiting and staying in Toronto. I had been to Toronto Pearson International Airport (YYZ) before, but never had the opportunity to visit the city. I decided to book with American Airlines due to the very low prices and because it will most likely be my last opportunity to visit the Admirals Club located at YYZ airport due to the recent enhancements to the Citi Prestige card.

Chicago O’hare to Toronto Pearson International (CRJ 900)

When booking I decided to book the last flight of the day due to the low price and the ability to standby on earlier flights if necessary thanks to my AAdvantage Platinum status. On Thursday afternoon, I received an email from American Airlines that my complimentary upgrade had cleared for my scheduled flight. I decided to wait for the flight to enjoy the added comfort and free alcohol of Business class.

After arriving at the airport via Chicago’s CTA Blue Line on Thursday evening I was greeted by one of the worst security lines I have ever seen in ORD’s Terminal 3. For a while American had frequently changed security line locations, but it appears the airlines has found a setup that works for them and it’s terrible for TSA PreCheck passengers. The lines were so terrible, I decided to go through the security checkpoint for “normals.” Not surprisingly, I cleared security before may people who entered the TSA PreCheck line at the same time I entered the non PreCheck line.

Next, I proceeded to the Admirals Club located between the H & K gates. The lounge is currently under construction and the crowds were overwhelming. In general, visiting any airlines lounge early evening on a Thursday or Friday will yield large crowds due to the timing of International departures, but the loss of space because of construction made the club especially crowded.

After about an hour I walked to the gate to board my flight to Toronto. I was very pleased to be serviced an alcoholic pre-departure beverage in First. Pre-Departure Beverages are often hit or miss, but the crew on my flight was on top of everything from boarding to deplaning. Once in Toronto I requested an Uber, which was a mistake (more on that later), and was on my way into the city.


I won’t go into too much detail about my trip, but I was lucky enough to stay at the Thompson Toronto Hotel which features a 360 degree rooftop bar/deck which overlooks the CN Tower and Toronto’s downtown.

Oddly enough, Toronto decided to shut down the Gardiner Expressway for Fall Maintenance on the weekend of our visit which made traffic into and out of the city especially terrible. The city is quite walkable and public transportation is extremely easy to use. We also took a day to drive to Niagara Falls and Niagara on the Lake which was an amazing experience. More to come on the weekend in Toronto soon.

Toronto to Chicago (CRJ 900)

After spending $60.00 on a cab from the airport to downtown Toronto I decided to try a different route to get back to the airport. I took an Uber from our hotel to Union Station and took the UP (Union Station / Pearson) Express from Union Station to Toronto Pearson International’s Terminal 1. In total, the cost was about $8.00 for the Uber and $12.00 for the UP ride. The whole trip took well under an hour and was much more enjoyable than sitting in traffic. If I ever am fortunate to visit Toronto again, I will definitely take the UP into the city rather than paying for a cab.

American Airlines would not let me receive a mobile Boarding Pass for my flight back to Chicago and when I checked in at the airport it was very clear why. When my boarding pass was finally printed at an automated kiosk I quickly noticed the dreaded “SSSS” on either corner of my boarding pass. SSSS means you have been randomly selected for an “enhanced” screening at the airport. Overall the experience was painless and before I knew it I had cleared US customs. When traveling from Toronto (YYZ) or other major Canadian airports to the United States you will often clear customs prior to departure which means when you land at your destination it is as though you flew domestic. It adds a few minutes to your departure, but makes the arrival much more enjoyable.

My flight back to Chicago was again on a Bombardier CRJ 900. I have written about my love of regional jets previously and this flight was no exception. I personally enjoy the ability to gate valet bags to simply pick them up on the jetway at your destination. I also love the 2 by 2 seating arrangement in economy and 1 by 2 in first. Middle seats are never fun and it is nice knowing there is not really a terrible seat on the plane in case you cannot select a seat for whatever reason. I also tend to enjoy the added “turbulence” of flying on a smaller plane. I like knowing that I’m flying though the air at hundreds of miles per hour! I just with the CRJ had the same large windows found on the EMB family of regional jets.

After a long weekend, I was in need of a pre-departure beverage (I had again been upgraded), but was told by the flight attendant alcoholic beverages cannot be distributed prior to take off due to customs regulations. I quickly forgot, fell asleep, and woke up in Chicago.

Final Thoughts

I made a mistake paying for a cab into Toronto. The UP train is extremely clean, cheap, and comfortable. Once at Toronto’s Union Station it is very easy to get anywhere in the city via Uber or Taxi.

I was also very happy with my service from T-Mobile One during my time in the city. I had unlimited calling, texting, and data for the duration of my stay and had impeccable service throughout.

Unfortunately, I did not make it to the YYZ Admirals Club due to the 4 S’s which appeared on my boarding pass.