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Advice on where to look for hotel in Chicago area

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I'll be going on a road trip with friends over Labor Day weekend. Originally our plan was to not stay in Chicago - just go in and out "on our way" from Indianapolis to Michigan - but due to some scheduling issues and the length of the drives, we're now looking at staying a night in the area. I've been to Chicago several times and am familiar with the downtown areas, but have never been there with a car and do not know the suburbs at all.

If you had the following situation, where would you look for a hotel?
- Three women in our 30s
- Driving in from Indianapolis on Friday morning
- Heading to Fremont, MI Saturday morning (north of Grand Rapids - Google takes us along Lake Michigan from Chicago proper); willing to either stay in Chicagoland or get a little ways into Michigan Friday night
- Will want to do some touristy things (mainly eat, let's be real) and meet a friend who lives on the north side somewhere (not my friend, so I don't know if that means Wrigleyville or what)
- Completely comfortable with public transit, especially the el
- Budget is a priority - basically, we want to go as inexpensive as possible while being safe, clean, all that. We don't need an exciting place to stay; I just don't want to book us a hotel in a scary or extremely inconvenient area (my friends from the Midwest have already said "NOT Gary!")

Thanks in advance for any advice!

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