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Renaissance
Most hotels are in the loop or river north area. They're going to be central to most the city has to offer. Pick one and uber or take the el if want to branch out to the various neighborhoods.
I liked the Gwen
I like the Blackstone. It’s just on Michigan and right across from Grant Park. Nice views from a lot of rooms, great interior and has a lot of history
Gwen is nice!
W
Gwen is my favorite in the Loop. I also like both Ws (Lakeshore is nice in summer due to views).
The Robey is an SPG hotel in Wicker Park. Totally different (and better in my opinion) vibe than the Loop or River North
Blackstone or JW
JW
Gwen or ritz
Renaissance
I live in wicker and would also suggest the Robey. If you’ve seen one W or Renaissance you’ve seen them all, but Robey is a unique hotel, and wicker meets your criteria of exploring a new part of the city