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FOR SURE the Shedd Aquarium. It will keep you busy for a whole day.
Walking around Michigan Ave. is fun all by itsself and if you can handle window shopping then you'll be completely entertained.
Also, if you can catch a show, its really an amazing experience. They have some of the best show's and talent.
There is a lovely outdoor skating rink right on Michigan Avenue at Millennium Park in the winter. The line is crazy long but you can skip the line if you bring you own skates. There is a nice restaurant adjacent to the rink so if you don't want to skate you could always have dinner there and watch the skaters outside.
We went there a year ago in the fall. I second Shedd Aquarium although if you spend a little more you can get a 5 day pass to all the museums! Also walking along the lake is beautiful ...there is this amazing fountain.
The museum at the Art Institute of Chicago. It is free from 5-8pm on Thursdays!
I live in Chicago and have to entertain a lot of family and friends. The Shedd Aquarium is really fun. They just reopened the beluga whale exhibit.
Things to do off the beaten path:
1. Christmas kindlemarket Daley Plaza in the Loop--http://www.christkindlmarket.com/
2. Chicago Pizza & Oven Grinder---They take only cash. Expect long lines for dinner. The restaurant is located in Lincoln Park on Clark Street across the street from the site of the infamous St. Valentine's Day Massacre.
3. Chicago History Musuem also in Lincoln Park on Clark Street.
4. Wrigley Field
5. Millenium Park
Check out hotwire for deals on hotels......but check early b/c December is a busy time for holiday shoppers. The most central location to stay is in the Loop, MI Ave/Watertower, or Gold Coast. You can take the CTA or cab in less than a 20 minute ride.
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So my husband and I maybe taking a long weekend in December and Chicago is our shortlist. So I'm looking for ideas-where to stay, where to eat, what to do? We do have a small budget so we can't go all out. It'll probably be the weekend before Christmas. Our birthday's are both in December so it's going to be a combination Birthday/Christmas present to each other.
I would love to hear any suggestions you all have!