Smartphones don't come cheap, but some are certainly more expensive than others. Across carriers, previous generation phones such as the iPhone 5s, HTC One M7, and LG G2 are generally on the cheaper side (around $99 on a two-year contract, sometimes less depending on the carrier). The new Moto X, which is an excellent phone, also falls into this price range.
Newer phones like the iPhone 6, HTC One M8, and Galaxy S5 will cost more (about $199.99 on a two-year contract), but if you're looking to save a few bucks the phones above will suit you just fine. Phablets (i.e. giant phones like the iPhone 6 Plus or Galaxy Note 4) start even higher at $299 on contract.
But, keep in mind, you'll be committing to a two-year contract at those prices. So even though the phones may not seem dated now, if you opt for a previous-generation phone it will be about 3 years old when you're in the second year of the contract.