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*keithandkristi*
Hey! Here is the info I can give you about the following cities:
Chicago - I was there for one weekend while a friend of mine was on a business trip and a few of us tagged along! I don't remember the name of where we stayed, but it was a major hotel (Marriott/Hyatt something like that) and on Michigan Avenue. I would say, anything on Michigan Avenue is a good location, you can easily walk to stores and restaurants. Rush St has all the bars and nightlife, and make sure you go to the John Hancock tower. There is a lounge at the very top, enclosed in glass so it's an awesome view of the city. It's a little dizzying, but def worth it!!
Boston - I went here one weekend with a friend and stayed at the Omni Parker house hotel. It's apparently the place that the Boston Cream Pie was invented - and it's a very old, historic building if you are into that kind of thing. It was in a GREAT location and we walked everywhere. Make sure to get to Fanueil Hall (shopping and dining) and do a Freedom Trail tour. Newbury Street is the high end area of the city and it's near Boston Common (big park) which is beautiful. We went to eat at Cheers - which is the tourist attraction, but kind of overrated LOL - but they have large cardboard cutouts of the Cheers characters. Make sure to visit the North End for great Italian food.
Las Vegas - I've been here 4 times and LOVE it!!!! I've been there with a group of girls in my single days, and I've been there with DH (before we were even engaged) and it was a great time each time. Check out Mandalay Bay or Treasure Island hotels, I've stayed at both and they were fantastic. But basically ANY hotel on the strip is going to be great and in a great location. Make sure to eat at the Mario Batali resturant Enoteca San Marco in the Venetian, Kahunaville in Treasure Island, those were some of my favorites. And check out any of the Cirque du Soleil shows, the Dolphin & Lion Habitat @ Mirage and the free exhibits (Lions @ MGM, the Pirate show at TI). And make sure you buy a crepe at the Paris hotel - I wouldn't leave without one!!!!
Have fun!!!
Re: *keithandkristi*
Wow! Thank you soooo much!! This is all AWESOME information! I was looking at vegas trips and found some good prices on the Mirage. I will DEFINITELY check out TI and Mandalay Bay! Thanks so much! I am so excited to start really planning!
Kristi
that's too funny!
I copied your post and emailed it to my DH and he was all sorts of excited! 
I checked out some of the places you suggested in LV and they look awesome!
In LV...do you have to pay to go in the pool or to just get a chair or cabana?
When you are a guest of the hotel, you do not have to pay to use their pool. We did usually get up early to get a good spot though, especially if it was a weekend. There are cabanas you can "rent" but for hundreds of dollars. You can decide if that's worth it