re: Chicago Itinerary (Thoughts/Changes/Recommendations?)

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Christkindl Market, ice skating ribbon in maggie daley park is great, zoolights at lincoln park zoo.

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Christkindlmarket is/was a favorite of mine during the work lunch hour. Nice change of pace and a lot of good food + vendors.

Agree with the above suggestions + would add seeing the Christmas tree in Millennium Park.

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A lot of good holiday pop up bars as well.

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For sure. If I were to make a recommendation, go to a "pop-up" at a real bar and not something like Frosty's, which opens in a random building in LP once each year and serves up bad, overpriced drinks. If nothing else, though, there are plenty of Christmas decorations.