Short Visit...Tall Buildings: 36 Hours in Chicago

Updated: Jun 18, 2019

Chicago...The Windy City.

Chicago...The City of Second Superlatives (used to be 2nd largest, 2nd tallest building, etc.).

Chicago...36 Hours wasn't nearly long enough.


When I saw Chicago on the schedule I wasn't that excited. It wasn't a sense of dread, more a meh. I'd only passed through the periphery of Chicago once before. I'd never seen the buildings up close; never strolled the riverwalk, spent time in any of the museums, or taken in a sporting event. Chicago just wasn't on my radar as a great crew rest location or place to visit.


I surveyed the crew before we picked a hotel. A short stay is usually a fight between the forces of good and evil. A good crew rest angel sits on one shoulder and suggests you stay near the airport. You can bed down the jet, get to the hotel quickly, and enjoy a beverage at the hotel bar before turning in if you are lucky. On the other shoulder, the crew rest devil implores you to suck up the commute to get downtown and see what the city really has to offer regardless of crew rest length. At 36 hours we could easily give the angel both ears. The ayes had it and we decamped to the Fairfield Inn & Suites in downtown Chicago. The hotel is located about 1 block from the river walk.

Chicago Midway, it's like the only WWII era airport that kept all of the runways.

We landed early afternoon at Chicago Midway. Southwest was busy doing Southwest things...moving people at 420 knots in the air and 40 mph on the ground. It was quite impressive and orderly getting into the field. I was impressed by the precision (fly 180 knots...fly 160 knots...you may scratch your nose...) and the throughput. Bedding down the jet didn't take that long. A relatively short 30-min Uber ride later we were climbing out of the car at the Fairfield Inn & Suites downtown Chicago. I picked the hotel a.) because it was well under our max nightly rate and b.) because it was close to the Chicago Riverwalk and the shore of Lake Michigan. A quick change into running clothes and I was making miles from the Riverwalk to the Museum District. If I'd known how close I was to Soldier Field I'd have turned right instead of left after the bend at the aquarium. It's always worth it to see the gladiator arenas of our day up close.



The path along Lake Michigan is great! I'll make a right turn after the aquarium to loop Soldier Field next time.

On my way back from the run I took note of the various cruises available on the Chicago River. Being a huge fan of architecture, I decided to embark on the tours offered by the Chicago Architecture Center the next morning. They even offered a special "photography" departure at 9:00 a.m. Sold! I got back to the lobby, showered and ran into our Flight Attendant as she was returning from shopping for our flight the next day. We grabbed an excellent dinner at Beatrix together before I headed back and hit the sack.

I was up at 8:15 a.m. the next morning for a quick bite and walk over to catch the photography cruise. The river offers the best view of the buildings. It's wide enough to give you a proper angle and the boat spins 360 degrees at a couple of intersections so you can take in all the views. I can't say enough about the volunteers from the Chicago Architecture Center. They state up front that they are volunteers and don't accept tips. That's a tall order, because these unpaid historians really pour their brains and passion out on the guests. The 90 minute tour flew by as I tried to absorb the fire hose of info aimed at us. We were also lucky enough to be out on a Saturday morning in the spring. Sailboats from inland mooring points were transiting to Lake Michigan. The city schedules bridge openings in sequence to allow the tall masts of the sailboats to pass. I won't go into great detail on this gallery (WIX is not optimized for that), but don't hesitate to ask if you have questions.


36 hours wasn't enough. I could easily spend a week in Chicago on the architecture alone. I'm already looking forward to the next trip. If you have a chance to take in the city, I highly recommend a run along the lake and a architecture cruise on the river. It'll be just enough to whet your appetite for a second visit to the city of second superlatives!


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