Chicago Vacation Itinerary

All items subject to change on a whim.


1pm – Land in Chicago. Buy a map of downtown. Because smart phones are loserz, and maps are awesome. And wouldn’t it be adorable to write all over the map while I am using it, and then hang it on my wall as art when I get back? Yes, it would be.

1 to 3pm – Find a coffee shop. Read a book.

3pm – Check into hotel.

3:30 – 5:30 – MEANDER. IN CHICAGO.

6pm – Meet coworker for music in the park, and a picnic, in Chicago.



Upon waking (whenever you feel like it, but maybe not later than 9am)


Maybe do Frank Lloyd Wright tour. Maybe just walk around until you find something interesting.

Lunch – Eat a hot dog from a hot dog truck. It’s a rite of passage, even if you feel bad later.

3:15 – Architecture Boat Tour

Dinner – Eat deep dish pizza somewhere – maybe charm someone into letting you buy just one slice of theirs, because you are only one person, and do not want an entire pizza. Alternatively, eat one slice and give the rest to a homeless person. This is not about benevolence. It is about pizza.

8pm – Jazz Showcase



Morning hours – Explore the Art Institute.

Lunch – Find a salad food truck? Is that a thing? Yesterday, you ate a hot dog in the street and pizza with a homeless person. There has to be salad somewhere.

Afternoon – Sears Tower or John Hancock Tower. Because being high is neat? No, that’s not right. That’s about drugs. Because being high in the air is neat. That still doesn’t work. Because people like to be at the top of tall buildings. They say it’s neat.

6pm – Listen to live Blues music at Buddy Guy’s Legends

Who is Buddy Guy, and why would I want to go to his Blues club, you say?

Since we’re here.



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