A good cheap card would be an ASUS Xonar D1, they go for around $65 new. You could also look into getting a used Creative X-fi, Creative sells refurbished X-fi Xtrememusics for around $45, just avoid the Xtremeaudio at all costs, it's crap.
As for speakers, I'd go for headphones instead. Sennheiser HD-201s are great and you can find them for around $25.
In general, yes, there is a difference. However it largely depends on which sound card and which onboard card you're looking at, the quality of the audio you are listening to, and which speakers/headphones you're using. The Xonar D1 and most of the X-fi based cards will sound better than onboard sound, assuming that your headphones/speakers are not total crap.
You may want to look into getting a long-term pair of headphones like the Sony MDR-V6 which could run off the onboard realtek soundcard without a headphone amp. They're probably the most comfortable and best sounding headphones for the money and are definitely more durable than most offerings in the $50-70 range. Then you also have the option to upgrade your soundcard for an even better sound.
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