1. If possible, stay in a hotel that is close to public transportation. This will make exploring this gorgeous, easily-accessible city even easier.
1a. Do not discount a hotel simply because it does not have a bar. Friendly staff, comfortable beds, free breakfast buffet, and a waffle maker nearly make up for this lack.
1b. In terms of riding the "L," REALLY stay clear of the doors. They can eat you.
1c. The gong sound you hear on the train is not some nearby church bell tolling the time. That lovely sound is the "L" indicating that the doors are about to eat you.
2. If you have a chance to see
Sex and the City 2, don't.
2a. Even the two glasses of Prosecco you order at the fancy movie theatre will not make the movie any less offensive or depressingly unamusing.
3. If you notice a waitress sneaking around the alleyway after you’ve just ordered two beers at an outdoor bar, she may, in fact, be spontaneously quitting. Don’t worry though, another waitress is sure to be with you shortly.
4. Be warned: The crispy red snapper they serve at Sushi Samba Rio comes with a face.
5. Walking through Millennium Park and by the water is an ideal activity for any sunny day.
5a. Remember to wear sensible shoes.
5b. Don’t be afraid to ask other tourists to photograph you and your friends. But also, don’t wait around for twenty minutes, searching for the EXACT right person to take your picture. Any schmoe will do.
6. See a play at the Steppenwolf Theatre.
7. Sometimes, when you THINK the perfect snack would be either a Chicago-style hotdog or a slice of deep-dish pizza, the ACTUAL perfect snack is Chicago-mix popcorn from Garrett's: cheddar popcorn and caramel popcorn made separately and mixed into cheesy, sweet perfection.
7a. Eat in the park, if possible. While playing I Spy, if you can manage it.
8. The rooftop bar at The Wit Hotel is a scene. Enter at your own risk. However, drinks and snacks there are excellent.
8a. Avoid groups of sleazy, European men, unless they offer to share their champagne with you. In which case, have at it.
9. A late night supper at Park Grille is a superb way to end a really long, hot, eventful day. I recommend you order the crab cake and the house salad.
10. Sharing buffalo wings and a vegi deep-dish pizza is a good way to feel better about yourself after having a fat day while shopping. Especially if you’ve been looking for a birthday party dress and everything you tried on made you feel gross.
11. The Architectural Boat Tour is worth the price and will provide you with a deeper appreciation of the buildings that have surrounded you all weekend. And free cookies.
12. Be aware: The Sears Tower is now called the Willis Tower.
12a. Go to the Sky Deck. It’s super fun and educational.
12b. Standing 103 floors above Chicago actually makes you feel high. As in, not sober.
13. The walk to Tamarind on Wabash Avenue is sketchy. Take a cab.
13a. And keep the "L" tracks over you as a guide, otherwise you'll be confused as to how you ended up on this street instead of that one.
14. Take the bus to the Museum of Science and Industry. Not only will you be excited that you’re using public transportation so expertly but you will get a nice tour of the outskirts of the city.
14a. Here, you can enjoy such exciting exhibits as touring the U505 submarine, or seeing the development of a human fetus week by week, or attend a special lecture called “Poop Happens,” or watch as a 13-foot heart matches your very own pulse.
14b. Try not to go on a day the President is visiting or when it’s spontaneously pouring.
14c. And, by all means, check your departing flight status
before you get back on the bus to return to the city. You can spend a whole day there, and it’s more fun than sitting in an airport for five hours.
15. Remember, the remedy for avoiding a nasty hangover often involves a long walk back to the hotel.
15a. Be sure to buy SmartWater and/or Vitamin Water on the way to stave off dehydration. Sometimes Pretzel M&Ms are appropriate as well.
15b. The mimosa bar and hangover helper (virtually nachos covered in eggs) at Sweetwater on Michigan Avenue also help.
Safe travels!
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