Most of the shadows in this life are caused by standing in one's own sunshine. ~Ralph Waldo Emerson
Question #92477 posted on 07/26/2019 9:54 p.m.

Dear 100 Hour Board,

So. Homeless week. This year I'm headed to my ancestral home to spend it with family. I decided to take the train, since I'm not really in a hurry and hey, flying is getting boring. Thus, I've got one layover in Chicago near Union Station from 2pm-8pm on a Friday, after sitting in a train for over 24 hours. I feel like I should get out and do something.

Any recommendations? Amtrak has a baggage storage place, so I should be fairly free to roam around. Also, any recommendations on the train riding experience itself are welcome.



Dear Falcon,

Last year I was in Chicago for a little less than a day, and you can actually cram a ton of stuff into not very much time there. To eat, I would recommend Portillos if you want fast food that's still very on-brand for Chicago (try their Chicago beef sandwich!), or Giordanno's if you want deep-dish pizza (or both if you want to eat two separate meals in Chicago!). 

As for things to do, the Bean (technically known as Skygate) is a classic Chicago experience, as is walking around Navy Pier. If you have time to wait in line, as well as some money for admissions, going up to the top of the Willis Tower and standing in a little glass box 1,450 feet up in the air is pretty cool. There are also a ton of walking tours you can do for various things.

Good luck on the train, and have a blast in Chicago!



Dear Eagle,

I was just in Chicago for my sister-in-law's second wedding! (That is, she married the same guy but it was their second ceremony, as the first was in India.) Here's some recommendations:

  • Millennium Park
  • Walking the Lake Michigan shoreline
  • Walking the Chicago Riverwalk
  • Getting deep dish pizza (though according to our local cousin deep dish pizza is way overrated, so ya know, you decide). Either way, hit up the food scene!
  • If you have enough time and money, there's some cool cruises that take you up and down the river. We saw a ton of architecture tours that looked pretty cool
  • The Magnificent Mile, full of shops and great shopping experiences
  • Buy a one day pass on the local transportation. I think it's $10, but public transportation in Chicago is pretty great and an easy way to get around

Unfortunately I have no tips for train riding besides what Google will tell you (walk around frequently, don't miss the beautiful nature outside, stay hydrated (maybe that last one was just for planes?)). Sounds like a great trip though; hope you have a ton of fun!

-guppy of doom


Dear Sam the Eagle,

I know very little about Chicago, but I know lots about riding Amtrak for long periods of time from here to the Midwest. Here's my advice:

  • Wear comfy clothes. Unless you want to cram yourself into one of the gross little bathrooms, you'll probably stay in the same clothes, so make sure you can sleep in them.
  • Speaking of the gross little bathrooms, disinfectant wipes would probably be a good call if you don't like germs. The toilets don't sit around with water in them, as the train is sloshing and would cause the toilets to spill. The toilets do flush, but the waste doesn't go underwater right away which means smells stick around in there. Yuck.
  • Bring good train snacks! Food is available on the train, but it's way expensive. Bring whatever you want! I like bringing sandwiches, fruit snacks, pretzels, crackers, stuff that doesn't smell super strongly. You can also bring all the drinks you so desire.
  • Okay, so, Amtrak trains technically have wifi on board, but don't count on having it! I think the router is near the front of the train, and trains are very long, so you may not even be in range of it. Bring plenty of entertainment: books, music, a tablet with movies downloaded, podcasts, etc. You will have access to power outlets (there's two next to each pair of seats), so things you'll have to charge are all good. Don't count on having cell service either, at least while you're going through most of Colorado as you're going right though a desolate part of the mountains.
  • Bring a sweatshirt. It gets cold on the train.
  • Each passenger car has a place to fill up water bottles! 
  • Prepare for delays. I've never been on a train trip that didn't arrive at the destination late. Don't arrange to have whoever pick you up at the exact time your ticket says you'll arrive or they'll be waiting forever. Call them when you get relatively close. 
  • Ideally, the train won't be too crowded and you'll have a pair of seats for yourself. Feel free to pick whatever seat once you get on, and you'll put this little label over your seats so the train conductors can see your destination. If you have a set of seats, feel free to stretch out. There's a foot rest you can put up and your seat leans back. One of the (few) benefits of riding the train is that space isn't really a big issue, so don't feel like you're cramping anyone else when you stretch out. You definitely aren't. If things are going to get crowded, the train conductors will let you know to move your stuff ahead of time.

I think that's it! That's all I can think of for right now, anyway. Good luck!

-Quixotic Kid