The Illawarra runs on solo voices and duos more than full bands, and the list below shows it. Most of these singers give a Wollongong address, with a solid group down at Shellharbour and a few inland around Mittagong and Hill Top. That local base is the point: an act that lives here quotes a local job, not a job with an hour of the M1 built into it.
Sydney is close enough that its singers will happily come down, and some of what you find elsewhere online is exactly that. Before you compare two numbers, check where the person is actually based, because travel from the north is often the whole difference between them.
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Where the singer lives matters as much as the hours here. A Shellharbour act at a Shellharbour venue has no travel to price in, while the same booking taken by someone coming down from Sydney does. Each opening figure here comes from the singer's own listing, so if a number feels high, ask whether it carries a drive down the coast.
Down as far as Berry and Nowra is a normal night's work for most of them. Past Ulladulla it starts to be a long way home after midnight, so expect travel in the quote and possibly a night's accommodation. The Southern Highlands up through Bowral and Moss Vale is an easier run than the distance suggests once you are over the escarpment.
For one voice, there is plenty here and no reason to look north. The list thins out once you want a five or six piece band with horns, and that is the point where a Sydney act with travel priced in starts making sense. Enquire locally first, because a local singer at a local rate is hard to beat.
It is a common Illawarra booking and usually cheaper than hiring twice. The ceremony needs quiet acoustic and a battery setup on the sand or the headland, then the same person moves indoors, plugs in properly and plays through dinner. Agree the gap between the two and whether they need a spot to leave gear, since the venues are often a drive apart.
A lot of Illawarra weddings happen on sand or up on a clifftop with no power point anywhere near. Running off a battery is how the local singers solve it, so make that an explicit question instead of an assumption.
Some local singers run an acoustic dinner set and then switch to backing tracks to get a floor going, and some only do the first part. If you want both from one booking, find out which kind you are talking to.
An afternoon southerly off the water will flatten a voice and take a speaker off its stand. Have a sheltered corner in mind for the ceremony and tell the singer where it is.