Reddit mentions: The best midwest us travel guides

Cost of living in Chicago is not bad at all. If you're considering a 1BR apartment for $1,000 then the cost of food here will not be a concern to you. Keep in mind that if you decide to live downtown you might get hit with a higher sales tax than other parts of the city.

I would suggest living outside of downtown as most of Chicago does. I would suggest if you're looking for an area that is safe, affordable, and accessible then head north towards Lakeview / Roscoe Village.

The best tool I've ever found to finding apartments is PadMapper. If you expand the toolbar in the bottom left corner you'll find ways to sort things based on price, bedrooms, etc. They also have a crime overlay that you can toggle on and off. You could also do some research on a part of town through Everyblock. Although I will admit it will make you paranoid.

In regards to a car, I don't personally have one nor have I found it necessary to have one with me at all times. Chicago is a very accessible city via public transit with things like "the EL" which is short for Elevated Train. Its pretty good to get you from north to south and the busses here are good for east & west. You could also look into services like iGo or Zipcar for short car rentals. They're great for things like big purchases or IKEA runs. Not to mention that Chicago is pancake flat with over 150 miles of dedicated bike lanes in the city.

I would also suggest a book like this for learning about specific areas.

If you have any more specific questions, let me know.

Yes, the One Tank Trip books & videos still an excellent resource, readily available via local public libraries or bookstore. Protip: Many other major cities also had a locally produced One Tank Trip series, available via local library, local bookstore or Amazon, they continue to be quite useful for vacations and such.

There is all kinds of little weird places to visit and great places to eat.

I recommend:

http://www.amazon.com/Mississippi-Off-Beaten-Path-7th/dp/0762750472

You can find stuff like it on the web too:

http://www.virtualtourist.com/travel/North_America/United_States_of_America/Mississippi/Off_the_Beaten_Path-Mississippi-TG-C-1.html

Here's the book I was talking about: [http://www.amazon.com/Weird-Illinois-Troy-Taylor/dp/B0045JK6N8]

Also found this page that looks like it has a lot of info for free: [http://www.prairieghosts.com/hauntil.html]

Just looking these up makes me want to explore.

This book might have some ideas for you. It's not 5-hours-away kind of stuff, but maybe you could string a few of them together and enjoy some back roads between them.

Ran across this book at a barber shop today. Although 2016 publication date, it seemed to be still current --- except for some of the off beat entertainment. It lists some standard tour book stuff, but mostly it fits your definition of less known.

https://www.amazon.com/100-Things-Chicago-Before-You/dp/168106023X

You could try the book Weird Illinois by Troy Taylor. His website also has a list of places http://www.prairieghosts.com/hauntil.html

State is 0 on the East-West.

Everything is well numbered in the city (except a few angled streets). If you look closely on the street signs they have not only the street name but also the street number.

You might want to get a Turner Street Guide

I was raised to only navigate the city using a Turner Street Guide. I have virtually no idea where lots of named streets are... but I can get anywhere with just numbers.

Get a book called, 50 hikes in Ohio. It's excellent. Also for poison ivy pack a tube of hydrocortizone cream (2%) and put it on as soon as you start to feel a persistent itch. Poison Ivy is everwhere.

https://www.amazon.com/50-Hikes-Ohio-Backpacks-Throughout/dp/0881504017?ie=UTF8&*Version*=1&*entries*=0