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Chicago Historic Homes: Must-See Events and Tours for the Holidays!

Chicago Historic Homes

 Must-See Events and Tours for the Holidays!

Explore the enchanting holiday spirit in Chicago’s historic homes! Plan your holiday outings with the exclusive details in this video!

(click on the time to go directly to that chapter in the video)

00:14 Home Alone House
01:13 Frank Lloyd Wright Home and Studio
01:58 Driehaus Museum
* 02:28 Pop-op Concerts
* 02:53 Saturday Santa
* 03:03 Trunk Show
03:16 Glessner House
* 04:02 Gingerbread House Decorating for the Kids
* 04:18 We Wish You a Mattie Christmas
* 04:33 The Candlelight Tours
* 05:14 New Year’s Day Reception


For me, historic homes and the holidays go together. Let’s take a few minutes to look at what events are going on in historic homes around the Chicago area, and I encourage you to get out and take a peek at whatever events you can fit into your schedule. First of all, historic homes, lots of us think of the Home Alone House, which is in Winnetka, but some others might say, “It’s not an historic home,” but it is. It was built in 1921. It is a 243 square foot home. The last sale was in 2012 for 1,585,000, although it’s been valued up to 2,383,000. Taxes on this in 2022? $50,000 a year, if you can believe. It’s a Colonial Georgian, sitting on a 114 by 206 lot. Built in 1921, the Home Alone movie was filmed in 1990, if you can believe. And let’s see, what else?

And that’s just the story. It does not have any home tours, but I just threw it out here. I thought it would be fun to chat about. All right, let’s go on and talk about the next one. Frank Lloyd Wright Home and Studio. This is in Oak Park. This is where Frank Lloyd Wright lived, kicked around, experimented. It is a wonderful tour. I got to go and visit it a few years ago when my husband, Tom’s cousin, Wayne, came to town and he encouraged us to go. We had such a wonderful time. December 2nd, they have a Home for the Holidays event, “Bring your family and friends for a tour of Wright’s Oak Park home, decked for the holidays with the spectacular tree decorations,” yada yada. Christmas was a big deal in the Wright house, and his son spoke very fondly of their time in the house at Christmastime, and this is a great event, I encourage you to check that out.

Driehaus Museum in River North, one of my favorite places. Richard Driehaus was a philanthropist and big fan of architecture in the city. He helped to save lots of properties. His foundation now supports Historic Homes. And the Nickerson Mansion, that you see on the screen here, was lovingly renovated and it’s a wonderful property. They have the home itself that you can visit, and then they also have exhibits that come from time to time.

Over the holidays there are some pop-up concerts that occur. The concerts themselves are free once you pay for admission into the museum. And you’ll see we have Kwanzaa, St. Lucia, Hanukkah songs, caroling with the St. James Choir between four and 4:45 on the days you see on the screen here. Highly recommend that you go check it out and take a tour of the museum.

Saturday Santa is coming up on December 2nd. Make your reservation to visit then, or the other thing that you might want to check out is the Trunk Show on what is that? December 16th, where they’ll be selling some vintage jewelry, clothing, and other treats. The Driehaus Museum is beautifully decorated over the holidays and certainly well worth your visit. Glessner House. Glessner House is one of my favorite places in the city for Historic Homes. Imagine that you were in the late 18 hundreds in a Victorian, very vertical home, standard for its time and this wide, very sturdy stonehouse goes up across the street. You must have thought, “Holy smokes, these people are insane.” But this Richardson Romanesque house is beautifully preserved. Lizzie and I, my daughter, took a tour of this house a couple of years ago. We did the candlelight tour and I was struck with just how gorgeous this home is. They have several things for you to do during the holidays.

This is what one of the rooms inside looks like. You can see it’s just gorgeous. First of all, gingerbread house decorating for the kids. The 10 to 11:30 is still available, but one to 2:30 is sold out. Highly recommend you jump on that right away if you’re interested or plan to do it next year.

The next thing is We Wish You a Mattie Christmas. Mattie was the cook for the Glessners, and on December 3rd, it’s sold out now. But again, plan for next year. Wonderful event, wonderful time to visit.

The Candlelight Tours are available, and as I mentioned, they are really fantastic. Here’s a picture of the foyer. The rooms are so grand and lovely. It’s 17,000 square feet, if you can imagine. I think I mentioned, but if not, I’ll say it again. 1800 South Prairie Apologies. 1800 South Prairie, right next door to the Clarke-Ford House, which is the oldest house in Chicago, which typically would have tours, but right now it’s closed for renovation at the end of this cul-de-sac, the Marshall Field Mansion. It’s not a tour available. There are condos in that building, but it’s a wonderful part of Chicago that if you haven’t seen it, I highly recommend that you visit.

And then New Year’s Day Reception, it was [foreign language 00:05:18], however you say it, that on New Year’s Day to have an open house and people would go and visit each other’s homes, and welcome in the New Year.

From three to five on New Year’s Day, Bill Tyre is going to be there to play the Steinway and sing Auld Lang Syne, and it’ll be a wonderful event. I highly recommend that.

That’s it for Holiday Planning for Historic Homes in Chicago. Please look at my YouTube channel to find events for other areas around Chicago. I have a whole series of 30 videos that talk about different things that you can do in Chicago during the holidays. It’s my favorite time of year, and I highly encourage you to take advantage of all the wonderful things that Chicago has to offer. If you have questions about living in an historic home or questions about just the city in general, please reach out. I’m Anne Rossley with Baird & Warner. Let’s connect.

If you have inquiries about living in historic homes or anything Chicago-related, I’m here to help. Let’s connect and make your holiday season in Chicago truly magical! ✨🌆

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