Get this book first: Nightwatch: A Practical Guide to Viewing the Universe
It'll give you a comprehensive guide to buying a scope, based on what you intend to do with it, and what the pros and cons of each type of scope are. It's also a great reference once you have a scope. Truly one of the best backyard astronomer books out there.
A good general recommendation would be a newtonian reflector of the largest size your budget allows. Being able to transport it is also a factor. You'll probably want to get out of the city for a decent look through a scope.
For looking at deep sky objects (galaxies, nebula, basically anything not the moon or a planet) aperture is everything. The size of main mirror or lens. Light gathering is the rule, not magnification.
Avoid spherical mirrors (you want parabolic). Cheaper telescopes even by good manufacturers can have the cheaper spherical mirrors.
You can have good luck on the used market. Lots of folks sell their older scopes to upgrade. Most folks in the hobby are very helpful.
You can spend as much or as little as you want. A good pair of binoculars are great for looking at the night sky.
If you're really interested, get the book.
The book NightWatch was and still is a wonderful guide to the night sky.
Do you know how to use one? It’s not as easy as point and look.
NightWatch is a great book to read prior to your first scope. Most people will recommend a good set of binoculars until you get familiar with the dark sky. Also, a “star wheel” is a cheap investment, assuming you know how to use one (if not, it takes 15 min to learn), to aid you with your binoculars/scope as you begin.
Food for though- a lot of astronomy is not done in the visible light range, so looking through the traditional telescope is not what today’s astronomers typically do. It occupies a small portion of their profession.
If you're looking for a book I got NightWatch a few years ago and I've been pretty happy with it as a crash course in astronomy. It's not the most detailed book you'll get, but it's a great introduction. There are a few chapters that go into some (quick) science on everything from the Sun to the planets to deep space objects, a chapter on choosing a telescope, and one with a brief overview of astrophotography. It also has some basic charts for each season and then maybe 18 or 20 more detailed charts focused on the constellations and interesting DSOs to be found near them.
Due to being broke and too wimpy to stand out in the cold this winter I haven't taken the next steps of getting a telescope or more detailed sky atlas but I'd certainly recommend at least stopping at the library to find the book if not buying it.
I'd start by learning the constellations. Knowing your way around the sky makes it much easier to find what you're looking for. A book like NightWatch and the free software Stellarium would be very useful too.
As for buying a telescope, start with the guide on /r/telescopes. Binoculars are a great way to start, but when you want something bigger an 8 inch Dobsonian (around $400) is usually recommended for visual observing.
I enjoyed NightWatch: https://www.amazon.com/NightWatch-Practical-Guide-Viewing-Universe/dp/155407147X
CloudyNights is a great astronomy forum that has an excellent beginner’s section with very experienced and active members that will guide you through your questions. (CloudyNights Forums)
Learn the basics and how to "get around" the night sky. "NightWatch" is such a good book that guides you through all the basics from constallations, what equipment to buy, and how to use it. (NightWatch).
DO NOT buy a $100 telescope. I know greenshadows360 was trying to help but that cheap of a telescope is a toy and will lead to more frustration. It won't hold focus, position, and they're very hard to use. Completely not worth it and many people fall into this trap, get discouraged and sell them on offerup.
$75-$100 will get you an -excellent- pair of astronomy binoculars. I have 2 pairs of Orion Scenix 10x50 that I use constantly. They will let you see stars, planets, the moon, deeps space objects. I always have a pair in my car, they get pulled out constantly. In a 10x50, the first number is magnification – an object will appear 10 times larger, the second number is how big the objective lens is – the light bucket. You don’t want a whole lot of magnification, 10 to 25 is the sweet spot. You DO want a big objective lens, this is how much light the binoculars are collecting, 40-60 is a sweet spot here. Anything less and it you won’t see very much, anything more and they become too large and unwieldy.
Good luck, it’s an amazing and fulfilling hobby!
For practical backyard astronomy start with Terence Dickinson's excellent book Nightwatch and if you get a telescope or just want more detail move on to Guy Consolmagnos Turn Left at Orion.
Decent podcasts:
and for introductory tv shows, you can't beat Cosmos - Sagan's original or DeGrasse Tyson's reboot.
Surprised to not see anyone recommend Nightwatch yet! Although I'm not sure how it is for southern hemisphere....I've found it pretty helpful, though!
In that price range I would go with a reflector telescope as opposed to a refractor.
OP says it has to be from Sears, and I am not very familiar with their models. I have a Celestron refractor that was around $250 with accessories and it's pretty decent for a beginner scope, but I am by no means an expert (yet). Maybe next year I will upgrade to a better model, but something to keep in mind is some brands do not offer many accessories such as eye pieces and trackers, filters, etc. so you may wind up with a telescope that you cannot upgrade.
My suggestion would be to buy a well known brand such as an Orion or a Celestron that has a large amount of accessories available.
Another thing that is a good purchase would be a decent pair of binoculars and a star chart. With just those two things you will be able to scan the sky and start to learn where various objects are in the night sky.
Also, join the /r/astronomy and /r/astrophotography subs, there is a TON of expertise and knowledge on those subs. I have learned a lot in the past year by frequenting them.
Good luck!
EDIT: This is the telescope I have:
http://www.telescopes.com/telescopes/reflecting-telescopes/celestronastromaster114eqreflector.cfm
It's definately a beginner telescope but until you are sure you want to pursue the hobby I would not recommend spending any more than that.
I also ordered a filter kit and a tracker. The tracker is a nice option because it allows the telescope to follow an object through the sky. Without it you have to keep manually adjusting the scope once you find an object. Also a finderscope is a very valuable tool to help find objects. I think my whole investment was around $300, that would be for the scope, filters, finderscope, tracker and star chart, as well as a few books. Also, buy a book called "nightwatch", you can get it on Amazon for pretty cheap. It will be very useful when beginning astronomy.
You can't beat Nightwatch imo.
I would also recommend Bill Bryson's A Short History of Nearly Everything, it's not entirely astronomy - it goes into geology, biology and anthropology too for example - but it really gives a great overview of the basics of physics and our place and scale in the grand scheme of things. Plus it's fun.