I'll completely agree with chgoeditor, if it's a nice evening, head straight for Millennium Park, everything will be lit up. From there, Signature Room at the Hancock is a good option. The drinks are expensive, but remember that you're paying for the view. They charge $20 to get into the observatory on 94, so paying $10 for a beer on 96 ends up cheaper I'm told the women's room has a window, so nice view. No such luck in the men's.

After that, I would tend to say work your way back toward O'Hare as opposed to going to places that are off that general track, but that's me and traffic won't be a problem if you're going back late.

Generally back toward O'Hare: Publican, Haymarket (W Loop), Goose Island (Clybourn Corridor), Map Room, Piece (Bucktown), Revolution (Logan Square).
North along lakefront: Beermiscuous, Dry Hop, Atlas (Lakeview), Half Acre (North Center), Hopleaf (Andersonville)
Southwest: Lagunitas

If any of the breweries are ones you know and want to hit, definitely do those. Otherwise, some of these are reasonably close to each other. Publican and Haymarket are a couple of blocks apart as are Atlas and Beermiscuous. Piece to Map Room is about 1/2 mile (on Damen, mostly commercial, will have foot traffic). I would say skip Lagunitas unless you really want to go as there isn't much near it. ie, if you go there, it's probably your main stop.

From Piece or Map Room or Revolution, there are plenty of other bars on Milwaukee Ave to finish out your evening. If you want to save some $$, the Blue Line runs along Milwaukee up to Logan, so you can jump on the L back to O'Hare. This is also an option for inbound as well (check traffic, it's faster during rush hour, but by 9pm traffic may clear out enough to make a cab/uber faster)