Jim's Guide to a Perfect Chicago Christmas

Last December, I wrote a Chicago holiday activity guide of all the things I love to do around Christmas and this year to spice things up, I invited my dad – who you guys know as Jim – to write give his own top list of things to do for the season. So below is a list of all the things you should do with your own Dapper Dad (or mom or friend or uncle or whomever!) when the time allows:

1. Ice Skating at Maggie Daley Park followed by drinks at Offshore at Navy Pier. 

This ice skating rink is particularly fun because like the city of Chicago explains it “it’s a multi-sensory experience”. It goes in a circle but has tiny hills and sharper turns so it’s more of a ride than going in one pace around an ice rink for an hour. Not too far away is Navy Pier’s newest bar Offshore. It is the nation’s largest rooftop bar and it has a roof so it’s got the views without the cold weather. I have also heard that they have dressed it up for the holidays!

2. Caroling at the Bean followed by drinks at Cindy’s at the Chicago Athletic Association Hotel. 

Every Friday from now until Christmas, there is Christmas caroling at the at Cloud Gate aka The Bean. Local choirs lead the singing and everyone gets a songbook at the event. The Bean is conveniently located across the street from Chicago Athletic Association Hotel which houses Cindy’s – another awesome rooftop that has great views, outdoor fires, and inside seating.

3. Drive around to see the Christmas lights of Sauganash.

The neighborhood of Sauganash in Chicago is known for its holiday decorations. Take a drive around the neighborhood and end your night at Fondue Stube for some traditional melted cheese and bread. My parents had one of their first dates here!

4. Chicago Symphony Orchestra for a holiday concert. 

The CSO does holiday concerts all month long, but the most fun ones (in my opinion!) are the themed ones. The Harry Potter concert was Thanksgiving weekend, but the Home Alone one is coming up soon!

5. A Loyola Ramblers game.

Not sure how this one snuck in here, but I am guessing Jim wants us to all go to a game with him now that he is a fair-weather fan lol.  In all fairness, he is an alum and this is where he met my mom so we will let it stay on the list.