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Chicago to Seattle is $259/adult roundtrip, including a weekend stay.
Monkie's given you more accurate weather to expect. And that's the air temperature. It will feel a lot colder with the wind. Seriously, you need to make sure that the little one has enough warm clothes for this kind of trip.
I can keep you busy in Chicago for 5 or 6 days no problem, virtually on museums alone. My question is that you've got at least 5 or 6 more days in your schedule to fill. Seattle is neat and worth a visit, but is there anywhere else you want to see? Grand Canyon? Disney? Gettysburg? This country is BIG (not that Oz isn't, but people don't drive across it too often), and I think that some foreign visitors forget that.
Honestly, I'd recommend using NYC as a base for those extra days and then taking the train to Boston or DC to see the sites. You could do the same in Chicago, but there's less to see and most of it would require car travel since train travel in the Chicago area is notriously congested (seriously, there's literally a constant traffic jam of trains within 100 miles of Chicago). Just a thought, though.
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