What are some discreet restaurants/ bars that you'd recommend for dates and meet & greets with clients? Places that are upscale but lowkey on weekday evenings.
 
And please don't say Tavern/Gibson's...

Outback, Texas Longhorn, Olive Garden. These restaurants are low key. But upscale enough not to be cheap.  

You're kidding right?

Nico Osteria and Boarding House are very discreet and well decorated. I've also had a decent experiences at River Roast and Joe's Seafood.

Lmao, I hope so :\

upscale... hahahaha

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Bandara on Michigan Avenue is always crowded but a
It is all booths for 2 or larger ones. It's quite dark in the evening except for one spot on the table.  

I'd say it meets all your criteria

once a year specials

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Considering that's where he works as a dishwasher lol

Check out yelp for date spots.

A table by the window has a magnificent view of the Water Tower and I find it to be secluded with rather subdued lighting.

Love Bandera and it is a great spot.  Here are some of my other favorites.  My brother and I always challenge ourselves to get the best answers to this question.  So funny that it was asked here.  

Le Colonial (upstairs)
3 Forks (booths near the bar)
Coco Champagne Lounge (just opened)
Drum Bar at Rooftop of Raffelo Hotel

The Franklin Room on, of course, Franklin between Erie and Huron. A little on the spendy side, but the food and drinks are quite good.

Farmhouse, on Chicago near Franklin. A nice farm to table place,  with a great bar.

dim and romantic!  Plus, you won't be able to tell if your date actually looks good or if it's just the drinks and lighting...

If you are REALLY looking for low key.  Try a bar like Metro or Liar's Club or maybe even Double Door.  If you don't jive with one another; one drink, one look, one sentence that could slice the evening into two.  Then, pay the piddly bill and part ways with no one being the wiser as these dive bars are not likely to have anyone you know there...  Just saying.

XXX-Giselle Parker

I second Boarding House!

I'd also add Chicago Cut Steakhouse and Black Bird. The staffs are both very good about discretion. Heads up, Black Bird is a little smaller and the seating arrangement is a little more exposed if visibility is something you'd like to avoid.