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Aaron! This is exactly the kind of thing I love to do. Thank you so much for these insightful suggestions. Very much appreciated. Most kind of you to take the time to scribble these thoughts down. :)

Thank you so much for all that, Aaron. Much appreciated. I liked Mercadito very much the last time I was in Chicago. Also, I had stopped into Xoco for lunch, something or other in a basket on their sidewalk benchy table, and enjoyed that too. The point being that your suggestions are spot on. Thank you again.

yes, now I only need a room from 9/1 to 9/3, preferably in the same place.

Thank you! Yes, I agree. Whole Foods is also handy for the salad bar for a picnic outside, if the weather wants to cooperate. Any fabulous reasonably priced Mexican restaurants nearby? With excellent food quality as I'm a foodie :)

First bid at four star $140 in Millenium Park area was accepted. I was offered the option of extending my stay, which I attempted to do, but my attempt was rejected. I was told that other agents and booking companies had access to these rooms, so I guess the W Hotel rooms for Labour Day weekend are done. I attempted to bid for 9/01 to 9/02 separately in the same area at $150. My bid was rejected.

Hotel Felix gave me the option of extending my stay, but the price they offered was something outrageous like $225 per night. I thought I'd be better off continuing to bid. My desired budget would be $150, preferably under if possible. Is that unreasonable?

Thank you, Aaron. That's an excellent tip. I was just wondering what the convenient and delicious food options were in the neighbourhood :)

Please advise how to bid for best deal on 4 star Millenium Park, preferably, or River North hotel from Friday August 31st to Monday September 3rd. What would the best likely starting price be for this time? Thanks:)

I first bid Millenium Park area at 4 stars at 90 and was rejected. Added NMA-River North area at 95--rejected. Added 3 1/2 stars at 101 and won the Hotel Felix for the four nights.

Started with University area in West end. Failed. Added Rittenhouse area at 120 and won Palomar. Very pleased.

AFter having my previous nights stays scattered here and there through bidding on Priceline on a recent trip to Chicago, I chose to pay a bit more on Hotwire to ensure that my three nights were in the same place. Hotwire was offering a 4 star hotel deal in the Financial area at $135 a night which I took. It turned out to be the Omni Parker House. Although I could have gotten a better price through bidding over several days, I was happy to be done w it. I am quite pleased w the value.

I've been in Boston from October 24th. Last week I bid for all my days together in three and a half and four star categories at $110 in both the Theatre District and the Financial area. I got only one night at the Courtyard Marriot Tremont in the theatre district. A poor place to stay as the walls are paper thin and it has a bit of a sleazy vibe.

Thanks! I've been in Boston from October 24th. Last week I bid for all my days together at $110 in both the Theatre District and the Financial area. I got only one night at the Courtyard Marriot Tremont in the theatre district. A poor place to stay as the walls are paper thin and it has a bit of a sleazy vibe. I went to Hotwire and bid on the next three nights in the Financial District only. The secret 4 star hotel they offered at $135, so I took it as it was worth it to me to not have to mess around further (after previous experience stalking for hotels in Chicago). I got the 3 nights together at the Omni Parker House, which I love. And now I shift to the Hyatt. Sorry, I didn't know how I was to separate and post this bidding journey of mine. Please inform for future.

First try the day before I wish to check in and stay for two nights. I entered a slightly higher bid to make it more likely that I'd get two nights together after having tried bidding last week. I entered only the Financial area and 4 stars and bid 125. Got it--yay!