Sometimes you wake up at four in the morning thinking you're going to San Francisco. And then sometimes you end up in Chicago.
The saddest part of the excursion is that I didn't get to see these monkeys:
The worst part was deciding to join up with another whim tripper who had a totally different take on a day in the city than me. Slow poke Snyder and her "jet lag"/"broken shoes"/"adjusting to a new city" reasons for making me split a $10 cab for a one mile trip down a well walkable city street were toast after a long hour or more. Sorry friend, I'm gonna walk the city on my own for a while, and no, you probably shouldn't have had that Cinnabun, candy, pretzel, chips, and soda on the plane. Enjoy your best ever very pepperoni pizza. I'm going to swank up with a vanilla bean creme brûlée 95 stories high at the Hancock Tower and see what this city is all about.
It seems most of Chicago's big name sites are within walking distance, and the ones that are not are at least visible from the sites that are (I.e. the massively and surprisingly far away Sears tower can be seen throughout the city and other parks and famous buildings from one of the several river and double-decker tour busses). I opted for the combo architectural river and lake tour (awesome and so worth $30 especially on a perfect weather day like I had) and lots of wandering.
I had one moment of panic on my day trip- about 7pm when my last-minute host (the son of a family friend) informed me that he'd be out on the town until some 3 am. Not wanting to drop $100 plus on a hotel, I started frantically scouring airbnb and couch surfing to find somewhere cheap and public transit accessible to stay the night. Not 20 minutes later, my MTC companion JoAnna texts me to report that she just landed at O'Hare, in town for her sister's graduation the next day, she saw my post on Facebook and did I need a place to stay. SAVED! I spent the evening with the Hunter girls in a trendy Chi-town neighborhood, ate amazing Mexican food, and slept on a safe, comfortable couch.
Good thing, since I spent most of the rest of the day at the airport, trying to get home.
My recommended itinerary for one day in Chicago:
Take the Blue Line into the city and get off at Clark and Lake.
Walk east on Lake and marvel at the public transit miracle that is the L
Head North on Michigan through the Miracle Mile of high end and window shop (I found my dream red lipstick at Saks and the sales lady offered to let me store my bag behind the counter).
Notice amazing buildings along the way: The Wrigley Building's Sky Bridge, the sand-castle looking Water Tower Building, and famous HQs for places like the Chicago Tribune and Donald Trump)
Book a ticket for a river tour for later in the day. I quite enjoyed Wendella's 90 minute river and lake tour but I'm sure they are all great.)
Head to John Hancock tower, not to the Observation Deck but the Signature Lounge. They have a small, reasonably-priced menu, free wifi and spectacular views on all sides. While you're there look up and book a ticket to something - anything. There are tons of shows, described in detail at theaterinchicago.com, for any taste. Concerts, Broadway, Blue Man Group and Cirque. If nothing else, ask someone for a recommendation for a good comedy club or jazz bar. I didn't do any of these things on my day in the city but it was not for lack of options or an overwhelming price range. Tickets to some shows started at $10.
Head back south and go on your river tour
Continue south to one of the many parks along the water. I ended up at whichever one houses The Bean, a giant, mirrored lump shaped like a bean.
Wander around the streets west of Michigan and find dinner. If you have time, take a bus north/west towards the Lakeview or xx neighborhoods, where it feels safe and where people actually live and the variety and quality of restaurants seem to reflect that. Just ask someone on the street which bus to take. Everyone seemed to know how to get around via public transit.