One of the best places to see the Chicago skyline is from the 94th floor of the John Hancock Center. Aptly renamed the 360 Observation Deck, the platform provides does exactly what its name suggests: Views of Chicago in all directions.
Monday is the one day that tripods are allowed (9AM to 11PM). If you want long exposures, you need a tripod. Take your selfie, if you must. Most people never look at results after the initial chimp. And don't use flash to illuminate the skyline, as many do.
Best to position yourself in one place over a 2.5-hour period. The changes are gradual, but dramatic. Today, the Chicago skyline was partially cloudy: Mid morning there were high cumulus clouds and large blue patches. As the day progressed to late afternoon, the skyline turned dark gray in portions, with the sun lighting the city. I kept looking west, and I knew the city would be quite dramatic once the sun dipped below the cloud cover, particularly because the clouds were dissipating in the west. And that is exactly what happened. Flip a switch. Boom. And as the sun disappeared, so did the cloud cover, leaving a pink Grand Canyon sky. And a rainbow. And then solid turquoise.
As a resident and photographer, I buy the one-year pass, which costs $100. When the weather is interesting, I hop on the 146 bus, and in 15 minutes I am at the top. For tourists and those who aren't as obsessive, the admission price is $20.50 ($13.50 for children 3 to 11). The deck is open 9AM to 11PM 365 days a year. Those buying tickets online receive a 10% discount. If you have proof (government issued ID) that you live in Chicago (a 606** zip code), admission is 50% off for one adult (with up to 3 children).
Most skip it, but there is a terrific documentary running on the northeast side of the deck about the history of the John Hancock Center. It runs continuously on a 20 to 25 minute loop. On the northwest corner there is a small cafe (dubbed Architect's Corner), with a full bar, fast food, and gelato.
If you are looking for a meal and a view, visit the Signature Room. It has been about 20 years since I dined there. As I recall, the food was not bad, but as is often the case with restaurants at the top of tall buildings, it is overpriced for what you get if you don't take the view into account. The better deal is the Signature Lounge on the 96th floor, which offers drinks and light appetizers, but the same view. I forget the access point, but there is an internal staircase between the Signature Lounge and the Signature Room. If you are not interested in dining at the top of the building, you can dine at plaza level, where you will find a Cheesecake Factory (always crowded), a Starbucks, and a soon-to-be open Benihana.
Photographer's Note: Today's series is right out of Monet's "haystacks" bag of tricks. I would have had a fourth photograph but for the small children and large adults pounding on the radiators and rails where my tripod was resting. I would prefer to have it on the floor, but my lens skirt's suction cups would not attach to the windows. I am going to have to come up with a work-around. Vibrations are problem with all exposures, but particularly with 40 second exposures.
8:22PM: The Sun Dips Below the Clouds, Producing a Rainbow on the South Shore
7:53PM: The Sun is Still Largely Above the Clouds, Except for a Snippet that Illuminates Tower Tops
7.28PM: Rain Showers are Visible in the Distance