As someone who lives in Chicago without a car, it's definitely most convenient BUT keep in mind parking and make sure you ask whatever hotel you're staying at about it since most clients will be driving and spending $40+ on parking is a joke. I do incalls out of hotels, so I can send you a list of the best ones for parking if you PM me.
Staying downtown near Mag mile or By the airport? We stayed near Northwestern once and that was fun but not very convenient... Thoughts?
The Blue Line goes directly from the airport to downtown, so it's very convenient even without a vehicle. Of course you can take a cab if you hate public transit, but I thought the Blue Line trip was very easy. Once downtown, cabs are abundant and you can easily catch a cab from the Loop to your Mag Mile hotel. I don't know what the airport is like in terms of things to do, but it seems pretty easy to get around from downtown and I had a very nice time there.
Good luck planning your visit!
~ Zoey
...i'd suggest staying downtown. Logistically, you could get clients either near O'Hare or downtown... but if you want access to outing destinations and date spots, i'd suggest downtown. I recently had a staycation at the Hotel Allegro, and i found it to be really lovely for the money spent.
Hope your planning goes well! Feel free to send me a PM if you have any questions or would like some help in planning. 
-Erin
There are blue line closures so its not quite "direct" from O'Hare to downtown, but they will have shuttle buses. If you come in from Midway, the Orange line is direct to downtown, but you might have to change trains alone the way.
I think we will split up the trip half in downtown half at ohare!
Thanks though... Hope to see everyone soon!
Lets meet for drinks Erin if your around!
As someone who lives in Chicago without a car, it's definitely most convenient BUT keep in mind parking and make sure you ask whatever hotel you're staying at about it since most clients will be driving and spending $40+ on parking is a joke. I do incalls out of hotels, so I can send you a list of the best ones for parking if you PM me.