One of the things I love about Chicago is you can share all your favorite seasonal activities with a beautiful cityscape. Going to the beach in the summer or like above, ice skating right downtown in Millenium Park. Free admission and skate rentals are just $10. November 17, 2012 through January 8, 2013.
German? No? Fan of Cuckoo clocks? I almost got one last year. They were adorable. Cuckoo clocks, that is. Not a German. The Christkindlmarket is a good place to find both though! Open from November 20-December 24th, this market is a must-see for the holidays. The perfect place to find a gift for your favorite craft-lover; nearly all items are handmade! The market features traditional German toys and ornaments to food and drink. Admission is FREE and located in Daley Plaza.
The Renegade Craft Fair travels all over the country to bring handmade and vintage goods twice a year. Each December, the holiday craft fair is held at the Pulaski Park Fieldhouse in Chicago. This is the essential shopping destination for the hipster crafter you know. I also found many things for myself, including burgundy geometric earrings similar to the great necklace shown above. Etsy store: thislovesthat
And if you're coming from out of town, staying downtown is nice, but I know something better. In the Northwest neighborhood of Logan Square about a 15 minute ride on the blue line, you'll come to the best B&B style hotel ever. At least that I've seen. Downstairs, an award-winning restaurant and bar (below).