Leaving major cities during COVID-19 pandemic

The question asks "I would like to know if there are any official recommendations on if this kind of travel is discouraged/forbidden, or even unofficial reasons why one option might be better than the other."

In the US, travel and similar restrictions are being handled mainly by state and local governments. Chicago is in Illinois.

The State of Illinois has prohibited non-essential travel. See EXECUTIVE ORDER IN RESPONSE TO COVID-19 (COVID-19 EXECUTIVE ORDER NO. 8).

"All travel, including, but not limited to, travel by automobile, motorcycle, scooter, bicycle, train, plane, or public transit, except Essential Travel and Essential Activities as defined herein, is prohibited."

The various essential activities listed in the order do not seem to me to cover leaving Chicago to stay with relatives or to avoid potential civil unrest.

In Norway people have done exactly this, and now the military is forcing people to return to their homes. They argued, that healthcare in rural areas is minimal or nonexistent, and that if the people get sick later, they will either overrun the rural healthcare centers, or not get treatment at all.

Coronavirus: Norwegians told to leave countryside cabins and return home

“Go Home!” Norway PM Orders Norwegians to Leave Mountain Cabins

If you do, self-isolate for 14 days before getting close to family.

Don't be "that guy" - you know the one. The selfish one who becomes the "index patient" for that county.

Treat it just the same as New Zealand is treating visitors. Can you go on a 6-week grand tour of the Lord of the Rings filming sites and all of NZ's wonders? Welcome with open arms -- but you'll be spending the first 14 days sequestered in a hotel room.

They have the right idea. Do that.

If your rural friends have a lick of sense, they'll make you do that anyway. Unfortunately many people do not have a lick of sense, and in the moment of hello, are far more concerned with being viewed as disapproving or stand-off-ish, and cannot resist going in for that hug.

So I wouldn't even see the family until day 15 and would stay in a hotel. Unless they really get it, and have a fully isolated in-law apartment they can toss you into.

Don't trust the country, either

Also don't go assuming everyone in the country is immune. You're not the only one doing this. You could sit out the 14 days and feel safe being all hugs... and unbeknownst to you 2 days earlier your family spent time with the Joneses who made contact 2 days prior with "that guy".

Operating on emotion will not work (wishful thinking, fear, etc). Operating on science, fact and unflinching care is the only reliable thing. And that's hard enough when you have to cat-herd a whole family into good practices they don't really believe in.

One more thing. Guns. There are lots of guns out there. Either don't touch them, or go all-in, learning gun safety, especially gun law (rules of engagement), then gun self-defense (guns are not an "I win button") - and squeeze off bare minimum 300 rounds among at least 5 trips to the range.

Let's suppose you succeed in getting away to your family living a few hours distant.

Have you stopped to consider the probable reaction of others in the community there. Things have got very nasty in the Scottish Highlands in relation to numerous campervans and motorhomes coming from England to escape the Coronavirus, overwhelming the limited food resources in a time of shortage, causing a health hazard as campsites have been closed by government order, and potentially overhwhelming overstressed medical facilities in a remote and scattered area. You can probably expect a violent reaction from many of the locals.