Will be driving with family to Chicago in late July for a three-night stay and would like to avoid the $40/night parking at the hotel. Considering dropping off the family at the hotel, and parking the car somewhere for a lesser rate to save on this. Probably more hassle than it is worth, but would appreciate any input re: whether this makes sense, and parking options if it does.

Without knowing the name or location of your hotel, it is next to impossible to answer this question.

I've done this. Long term economy parking at Midway Airport then take the Orange Line to the Loop. A couple of bucks to ride the El and about $12 a day parking.

Will likely be the Doubletree Guest Suites or Embassy Suites/Lakefront, both downtown.

$40 a day is outrageous and they just raised the tax per room as well, I believe. There are other places to park for less $$, but it won't be as convenient and you'll have a walk.

Underground Grant Park garage is less if you don't have a high/extra large vehicle. But it would be a walk across the river.

Maybe someone can give you a specific place North of the river, which would be closer to your lodging.

We just used one on Randolph for about $24 per day, but that one would be a walk as well. You will be closer to the Michigan Ave/Mag. Mile.

If it was I, I think I would just bite the bullet or use Grant Park underground and hike it.

$40 - yikes! That is awful. It was $30 last winter at Chicago Hilton and I had to suppress the urge to pitch a fit.

They are raising pricing to tourists in many of the Northern cities on this continent (not just USA) to the point that from a driving perspective, gas is not the primary cost quotient. Added area taxes and parking are just ridiculous.

And of course, there are always venues near to the hotels that have parking at 1/2 the cost. I think that some places are killing the Golden Goose.

Where are you driving in from? you could park on the edge of town and take a train in perhaps.

From Kansas City, but after our time in Chicago, we are going on to Michigan for several days.

Across from the Midway Orange Line Station, there is a private economy lot that's less than $9 a day. I've used it several times. Leave the car there, and take the Orange Line into the city for your three days. You won't need a car downtown, and 24 hr. parking in the Loop will be an absolute minimum of $20 a day, and probably closer to $30. However, Do Not park in the CTA park and ride lot. There is no overnight parking there, and you will be towed. You can just walk across the street from the lot to the train station.

There is a lot at Pipers Alley which is in a very nice neighborhood called Old Town not too far from your hotel (maybe a $6 cab ride). The lot is at the intersection of North Avenue and Wells Street (enter on North Ave.) The daily cost is $20 so it would be $60 for three days which maybe is not too bad. You can also park hourly.

Do mapquest.com for North Ave. and Wells St. and you can see the proximity to your hotel and see if it makes sense for you.

We park at Rosemont, it is right across the street from Stephens Convention Center it is 5555 N River Rd. 11 dollars,you pay upfront. We have stayed up to 10 days, and there is no added fee, just the 11.00 dollars. We use this alot when we are flying out of O'Hare.
But it is the same deal for Chicago because you walk to the blue line and take the El to Chicago.