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Decided to book the $139 for the 4*.  Like predicted it was Club Quarters Wacker@ Michigan. It looks pretty good from the website.  

If it was you, which one from the above would you book?  I'm getting nervous, Just going to book something.  Don't know either area, so going on all your recommendations.  I really appreciate all your help.

Just searched again, Hotwire seems to have a 4* in the theater district for $155.  do you think that would be any good?  The $147 isn't showing up when I search.

UGH.... Waited too long and neither deal seems to be up now.  Any other suggestions?  

I guess the question really is... What do you think the difference in accommodations with be from the 3* $147 to the 4* $169.  Do you think it will be worth it?  We got very cheap flights, that's why we chose Chicago, but also need it to not break the bank as we are a middle income family, and this is an extra getaway.  Would it be worth it to save the little extra and get the 3* with decent/clean accommodations.  Where I could use that little extra a night towards an attraction, or spend the extra $ per night to stay somewhere a little nicer, but not have the Extra $45 to spend elsewhere.  Trying to get the whole weekend to be under $600 for food, accommodations and activities.  The flights were booked with miles that I needed to use or lose, so I spend about $40 a roundtrip.  

Travel dates are this Friday July 13, 2018 to July 16, 2018.  I would like to keep it under $130 a night if possible but also want it to be an enjoyable weekend with my husband.  (Don't want to end up in a sketchy hotel)

My husband and I are taking a spur of the moment getaway weekend to Chicago.  We are flying into O'hare and am trying to find a hotel that will be within our budget, but also convenient to tour the city.  Neither of us have never been to Chicago.  We don't mind renting a car, and staying a little outside of the city, but after looking, it looks like it might not be that cost effective.  Also, I was limiting my search to 4 *  hotels, but are the 3.5 star hotels in the city just as good.  When we travel, we typically stay at a marriot or hilton...  Just looking for some advice as it is 4 days away and I don't have a hotel booked yet.  Just wanted an economical weekend away for my Husband and I in a new city.