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What is your favorite place to stay at in Chicago (area)? Hotel? We are looking for safe and easy to navigate. We are going to the Sade concert for our anniversary and need a place to say...but we are totally Chicago unaware. We don't know where we should stay or what to expect.
Re: Chicago Questions
I always use priceline for Chicago because there are so many hotels available. Downtown, I choose the Loop (#7 on the priceline map) and start with 3 and 4 stars. One time I scored a Hilton for $55, though I'd probably expect to pay at least $100 these days.
My parents booked a Travelodge directly for $100 because they were too nervous to try priceline. They said it was fine, but I'll bet I could have done better for them.
Hotwire is pretty awsome too. It doesn't tell you the name of the hotel but it gives you information like the star rating and a general vicinity the hotel is in. We were able to book 3 nights at a Sheraton hotel in LA for only $88 a night instead of the usual $150+ a night if booking directly through the hotel.
I hate 3rd party websites so I won't comment on that. If you are afraid of navigating Chicago, choose a hotel close to the concert location. Are you driving, flying, or taking the MegaBus?
If you haven't booked tickets, I'd honestly recommend the MegaBus. It's really not that bad and if your anniversary isn't too soon, the prices should be super cheap. Read $1 per person per way plus booking fees. We couldn't connect to the internet, but it looked like others were. You can bring your own snacks and drinks, but there are 2 stops (Iowa City plus whenever the driver decides).
We loved being right off the metro line in Skokie. It is a northern suburb, but we liked being away from the inner city to sleep. It was a quaint little suburb really. Anyways - if you aren't driving (or even if you are) the bus and train are great. We did a good amount of walking too.
We only got lost a few times (all on our first trip to the city and all on the first day or two), but were never in a scary situation or unable to get on a bus or train to get out. I was really afraid we'd be in a "bad" neighborhood at some point, but it never happened.
There is soo much to see and do there! Chicago is the one city I'd consider moving to actually because of all it has to offer! How long will you be there and over what dates? Do you have a budget in mind? I'd love to give you some suggestions if you want them.
Last August when we went to a Cubs game, we ended up staying 30min outside of Chicago, in Napperville. It was cheaper and there is a HUGE outlet mall close
SO that was a perk to go shopping after we checked out! 
GL!
OH! And AVOID the toll road! OMG! HORRIBLE! Just go a different route! I reccomend a GPS
my favorite hotels in chicago are the kimpton boutique hotels. we stayed at the hotel monaco the last time i was there and loved it! it's very close to the river and michigan avenue.
i've also stayed at the ambassador hotel and while it's old school, it's nice and close to michigan avenue as well.
restaurants - graham elliot, hands down! one of the best meals i've ever had. i also like carnivale, and the restaurant in the hancock building on the 63rd-ish floor.
I am a big fan of Priceline too. We usually stay at the O'Hare area (we've always had really nice hotels and no airport noise) and just take the train into the city. We've been in 4 star hotels for around $50 a night so it worked out great for us!
Wow, that's guys. You have all been sooo helpful.
We are planning on staying two nights and don't mind spending a little cash on the restaurant seeing as we don't get out much.
Lot's of great suggestions and things to consider.
Thanks soooo much!