Possibly the highest lounge in the world, the Signature Lounge offers stunning views of "The Grid" that is Chicago. There's no cover charge, drinks are surprisingly reasonable considering the venue, and jazz bands play on weekends. If the line's too long, check out Nomi on the 7th floor of the Peninsula Hotel across the street.
Trolley Tip: If you're pressed for time or want to keep the charge to four hours or less, skip either the Baton Club or Signature Lounge.
North on Michigan, west (left) on Walton, north (right) on Rush, west (left) on Division, north (right) on LaSalle, west (left) on North, north (right) on Clybourn, and west (left) on Webster until across from Webster Place Cinema.
Chicago's oldest wine bar (since 1994). An extensive wine list accompanies a menu of brie and pizza, set in a fun and comfortable atmosphere with cool bartenders. Nearby 404 Wine Bar is a viable alternate, if need be.
Time for a taxi, which you may want to have the bartender call for.