No need at all for a travel agent for something so simple.
MKE (Milwaukee) is a much better choice than Madison, usually the bigger the airport, the better the fares. So, But, Chicago would be best, I’d check first for Southwest Airlines from Chicago Midway (MDW) to Las Vegas (LAS).
No idea about parking costs. Southwest Airlines allows you to check bags for free.
There’s other budget airlines, no idea if they’re still flying. They definitely make their money on nickel and dime fees.
A cab from the airport to the strip won’t be too bad, Uber is also available, if you’re familiar with it.
Any idea of which Strip properties interest you? Do you have a timeline? I don’t think they’re all reopened. I’d book directly with the hotel. You’ll be ripped off until you cry with ‘’resort fees’ which will cause an extra $25-$50 to be added to the room rate PER DAY and they’re taxed to rub it in a bit more. They’re not optional these days and give you almost nothing. So, don’t be allured by the low room rates at first.
I wouldn’t bother with a car unless you’re positive you’re going to go out of Vegas. In their insatiable greed, Vegas hotels now charge for parking. A car is nothing but a pain in the ass on the Strip and that also means the driver can’t drink. Not sure if that matters or not. Plus, you’ll have to add time to the trip for car pickup and drop off. Oh, and surprise! They’re gonna rip you off with a bunch of taxes and fees to rent a car so expect to pay double the quoted rate.
Packages often don’t save you money, but once you’re a bit farther into checking rates, you can always look at them. The Southwest Airlines website has plenty you can look at.
Anyway, that should give you some information for a jumping off point.
Edited: I realize I came off a bit negative with the fees. They’re a personal pet peeve of mine, and serve as an unwelcome ‘gotcha!’ to infrequent travelers. On the other hand, few places in the world hand me free drinks.
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