Any information on the best area to stay without any hassle ie; key cards for elevators, parking, and also the safest area to stay. This will be my first tour in years and want to make it a great one. Also any ideas on where to eat, shop etc...  

Thanks in advance
Harper

From a client standpoint, a “Chicago” visit is really a tale of two cities. There is “the City,” Chicago itself, with its world class hotels, dining, cool coffee shops, and shopping. Staying in River North, the Mag Mile, and the Gold Coast are probably your best bet for an enjoyable stay and maximizing client opportunities.  The Loop, the financial district, is not really a good idea.
The other side of the coin is “the suburbs.” The two best options here are Oakbrook and Schaumburg. Plenty of hotel, restaurant, and shopping options. More chain type experiences available, but  nicer end chain options are available…you just won’t find 5 star accommodations or Michelin star restaurants. But, again, many nice higher end chain options, particularly steakhouses. The shopping? Major malls located in each suburb that can keep you very busy.
What I guess you need to know is that “City guys” don’t go to the suburbs, and “suburban guys” don’t go to the City. Parking and traffic are the two major impediments.  I guess you could say that the O’Hare airport area is a compromise, but again, traffic can be a challenge.  I’m not sure why our area does not get as many touring companions as other major cities, but my guess it has something to do with the unwillingness of potential clients to commit in advance, in these days of deposit only companions, when things like battling traffic can be overwhelming . But that’s just speculation

so much for all of that information. That was a lot to take in but very informative and I greatly appreciate all the details and it has given me a lot to think about and decide on that's for sure. I did try to post a trip there a few months back but to no avail and hopefully this time it will work out.  

I appreciate all the input.

Harper

Yeah. I think the best way to describe it is that the suburbs kind of just developed independently of Chicago, rather than being an outgrowth of it like in other cities. So many corporations set up shop *around* but not *in* Chicago in the 50s and 60s, and the infrastructure was built to suit the suburbs themselves rather than funneling into the city effectively.

I can speak to meeting providers in the suburbs, specifically Schaumburg, and it's atrocious for a carless client like me to get to. The hotels providers (both indie and agency) tend to congregate are in the northern part of that suburb, near an intersection of two interstates (there's like 8 interstates in the region, and only 3 go directly to downtown Chicago). They're at least a few miles from any commuter rail stations. So either I would have to take the commuter rail and then hope I can get an Uber out there in time to meet, or take an Uber from my place in the city (or even Rosemont, which is just outside O'Hare) and pay $60-100. And with traffic, you can't be sure you'll get there in time.  

I've been super hesitant about certain providers as a result, just because they're out there. One provider I did meet out there, I did by spending a night at a hotel in Schaumburg (because it was a morning meeting). It felt like a tacked-on expense.

A lot of providers here who want to get both "city" and "suburban guys" tend to do "mini-tours," where they'll do a few days in the city and then a few days in Schaumburg or Oak Brook, and/or a couple days in Rosemont/O'Hare as sort of an in-between. It seems to work, far as I can tell.

Thank you for that information. It really helps me a lot to decide where to stay.  I appreciate your input as well.  

Harper

I'll add just one more option to the mix.  The O'hare airport area.  

 
There are plenty of choices for hotels of all quality.  And, a less likelihood that you'll encounter keycards, etc.  Unfortunately, not the dining options that the city has, but you are:  Near the airport, at the intersection of two major expressways, and along the elevated (subway) line into the city.  A LOT of people are going through the O'hare area on the way in and out of the city.  It's roughly 20 minutes from the city by elevated train, 20 minutes from Oakbrook and 20 minutes from Schaumburg.

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