Headed to Chicago this holiday season?

Whether you're shopping along Michigan Ave, going to hang with family, or just looking to get to the city for some holiday cheer, Chicago has plenty to go do, including some pretty cool Christmas themed stuff.  So I've come up with a list of 5-holiday experiences that you should check out if headed to the windy city.

Most of this list is going to be best enjoyed at night, or at least closer to dusk, which in Chicago is like 4:30 p.m. this time of year, so you don’t have to be a night owl to enjoy Christmas in Chicago.


Let’s start off with a quick drink, in a cool spot, overlooking a great winter scene, and possibly Lake Michigan (depending on the time of day and weather).

You’ll want to stop by Cindy’s Rooftop Bar located inside the Chicago Athletic Association Hotel.

You can make a reservation and eat dinner at Cindy's, but if you're just grabbing that quick drink - once you get to the rooftop, don’t wait at the hostess stand, just walk around to the bar, and order a drink, then take it to the patio; which is open year-round and gives you awesome views of the surrounding buildings all lit up, as well as ice skating at Millennium Park.

A perfect way to start this "Christmas in Chicago" journey.


Next up, make sure your phone's charged up and ready.

Lightscape at Chicago Botanical Gardens – boasts that they have over 1 million light points throughout the gardens, which is perfect for Instagram shots.

So many great Insta moments including the “cathedral of lights" which has 100,000 lights and they have a fire garden as well.  You can also roast marshmallows by the fire.

Lightscape is going on nightly until January 5th.


Jump on the CTA Holiday Train! Or the Elves’ workshop train.

They’re both 6 car L trains that run throughout the city – on Saturdays the two trains run together.

The trains are decked out in Christmas lights and decorations including Santa riding along.  The holiday train helps provide food baskets for area charities around the city as well, so you’re helping a good cause.

The train runs a different schedule each day so that it hits the entire city, so CHECK HERE for the route.


Ok, we’ve done the family/sight-seeing stuff, now let’s enjoy Chicago Christmas, adult style.

First a stop at Griswold’s, which is the Houndstooth Saloon in Wrigleyville, they’ve transformed it into the world of National Lampoon’s Christmas Vacation.  You can drink in a replica living room from Clark Griswold’s house, as well as grabbing a drink at the tiki bar and they have an area that resembles the attic of the Griswold house, according to WAND-TV.


One more stop that will definitely put you in the Christmas spirit. It’s Frosty’s Christmas Popup Bar.

Here you’re going to get oversized Christmas decorations, live DJs who spin both your favorite dance music as well as plenty of Christmas songs. Frosty's has 4 bars, three levels and two dance floors. They call it the Ultimate Christmas bar.  Just look through the pictures, there are so many cool spots in Frosty's.

Oh yeah, quick fun fact - it’s open until 4 a.m.

Get TICKETS to party at Frosty's HERE.

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