Chicago - Getting to McCormack Place
 

I have to go to McCormack Place for a conference. Most nearby places are either already booked up or way overpriced, so I will need to stay farther afield. I will have a car, but will be flying into ORD.

Knowing how bad Chicago area traffic can be, would I be better off staying near midway and knowing I will have a long drive to and from the air[port, or staying north of the city and taking transit? Or maybe some other place I haven't thought of?

Staying at Midway and going into the city in the morning and back in the afternoon would be together with everyone else at rush hour. Stevenson Expressway is always backed up a lot at rush hour. I'd find a hotel in the downtown area and either drive to McCormick Place or use uber/taxi/publlic trasnport. You should be able to find reasonable priced hotels close to the Loop.

Why do you want/need a car if you're flying into ORD and your activities seem to be centered in the downtown area.

About a month ago it took me over an hour to drive several blocks in this area. Everything was gridlock.

I'll have a car because of plans in the evenings since I am in the Chicago area. I've never hung out south of the loop before, so I was unsure what traffic was like down that way. Sounds like it is pretty bad. Unfortunately most loop hotels don't have good parking, and there aren't too many good deals even then.

What is it like driving down to McCormick Place form North of the city? I have a few options up there.

Take the L everyone else does, and forget the car

Many convention hotels have a shuttle bus,

North of the city probably means O'Hare/Rosemont area as that is where most of the hotels are. Driving that route is even worse as the Kennedy Expressway is always gridlocked.
It's definitely doable as obviously a lot of people do it, but it will take you an hour plus to get from Rosemont to McCormick in the morning, and same or worse on the way back.
Best Western on Ohio used to have free parking until a couple years ago. I don't know of any other cars that charge parking.
If you must drive, it seems that staying near Midway would be your best option as you are halfway to the city as compared to most other commuters.

I would find a decent place to just park and ignore the car for trips back and forth to McCormack during rush periods.

Not sure what and where your evening plans involve, but would also evaluate the cost / convenience of NOT getting a rental car, and instead using Uber / taxi services for evening plans.
By the time rental cost plus parking is factored in, you could get pretty far with Uber, etc.

Driving into the Loop from outside the city is typically pretty lengthy and stressful, unless you are really going at off hours (like 3:00 AM). I don't know your budget constraints but I would stay somewhere in/around the Loop or north of the Loop, around Michigan Avenue. There are tons of places for eats and drinks in that area. And public transport allows pretty easy access to many of the places you are likely going to see. Also being centrally located reduces the cost of taxi/Uber/whatever.

If you can't get a hotel shuttle to McCormack Place, you can ride the Metra Electric commuter train line between Millennium Station (near Randolph St and Michigan Ave) to McCormack Place. The one way fare is $4.00 and the ride takes about 7 minutes. There are typically 2 trains per hour. You can get a 10 ride ticket for $38.00 and they just punch it every time you ride. This option is particularly attractive if you are staying in the north east part of the Loop or the southern part of Michigan Avenue. If you stay in the south east Loop area, there is another station (Van Buren St) that might be more convenient.

Metra Electric Schedule

Unless you have other travel commitments that require that you drive somewhere around Chicago, I agree with the other posters who advocate that you ditch getting the car and just take a hired car or the subway from ORD to your hotel and back and then use other forms of transport in and around downtown Chicago.

Not sure if you've had your conference yet, but I would stay somewhere downtown and take the Red or Green line CTA down to McCormick. Don't bother with a car, the traffic will be a nightmare.

Staying by MDW you can take the Orange and transfer to the Red/Green to go back south.

Also, some of those buses are allowed to use Chicago's little known "Bat Cave." This "Magic Road" is a 2.5 mile busway, running under the cross streets between McCormick Place and Randolph Street. No traffic lights, no stopping, and no traffic jams.