Greg Starling

PRICELINE EXPRESS: Free Internet Indoor Pool Pets Allowed Fitness Center Restaurant Business Center Would love food recommendations. We're doing a dinner cruise one night, but other than that, wide open.

Bid up to $290 using rebid for a 5* hotel, but didn't win. Went ahead and used the PRICELINE EXPRESS to get the 5* for $305, and it ended up being the Trump. Thanks again for all your help.

I would be comfortable maxing out at $285 before moving to HOTWIRE.

Unfortunately, my dates are not flexible, so that's not going to be an option in terms of saving money. From the hotel point of view, I'm looking for something that is upscale romantic, if that makes sense. What do you think about a strategy of a 5 star bid on Price.line, then if I can't find something in my range going to a 4.5* on Hot.wire? And Second City sounds like a great option for Saturday night - I'll definitely look into that.

I totally get not being able to upgrade, I figured I could probably add a few dollars on checkin or over the phone to get the view I want - obviously based on availability. I've never used hotline (just priceline) so I'll have to dig into the process, but it seems similar. Would you recommend the few extra $$ for a 5* or would a 4.5* be about the same quality? Again, I apologize for my Chicago ignorance. We're also planning on doing a dinner cruise Friday night then seeing the city Saturday. So any recommendations as "must sees" would be appreciated. Would be cool to see a show, comedy club, etc Saturday night. I'd love to catch the Bears/Packers game on Sunday, but I'm not too excited paying $300 a ticket for bad seats - so that could be a sports bar on our way out of town.

Looking to get away for two nights 9/26 and 9/27 to a nice upscale hotel in Chicago then head back on 9/28. I'd like to get in for $250 or less, but I could go higher if I needed to. I don't know Chicago so maybe a 4.5* or a 4* would be just as good, and I'm wasting my money so any local advice is appreciated. This is a trip for my wife and myself, and we really want a view of the lake from our room. I've had friends stay at the James hotel and W Lakeshore and they liked those a lot, but I'm not sure if I want to risk getting a lower end 4*. Any bidding advice / strategy is greatly appreciated.