I guess you need to make a choice from a couple options.

1. You can certainly stay out by ORD.

Pros: Puts you where you need to be following your inbound flight on Sunday. Puts you where you need to be for your Wednesday a.m. flight to Japan.

Cons: Long trip to Skokie by CTA, I'd suggest just cabbing it if this is your choice. Not in the Loop area if you like to get out and do things.

Nuetral: Fairly easy to take CTA on Tuesday for your West Loop meeting - involves either a bit of a walk depending on where your meeting is or a short cab ride.

2. You can split your stay and spend one night in Skokie and two nights either in the Loop or at ORD.

Pros: Puts you where you need to be for your Monday meeting but involves same trip from ORD as described above.

Cons: Split hotel and need to move halfway through your trip.

3. Stay in the Loop:

Pros: Central location for entertainment, etc. Easy CTA ride to/from ORD. Relatively easy trip to Skokie if you take the CTA "Skokie Swift", but check schedules to be sure how long the trip will take. Easy to get to your West Loop meeting on Tuesday.

Cons: Longish trip to Skokie on Monday. Need to plan to arrive at ORD in time for your flight on Wednesday.

If it were me, I'd choose the loop option.

If you decide on ORD, note that most of the hotels on River Road are walking distance to a CTA stop, as are the Hotels by Cumberland. The hotels on Mannheim are not. The ORD Hilton is probably the most convenient as that stop is essentially in their basement, and for an airport hotel it isn't bad.