Six Places in Chicago to Take Your Holiday Guests this Year


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There is really nowhere else in the world that does the holiday season better than Chicago. It’s not bitterly cold at this point in the year, and you still can enjoy the beauty of the few snowflakes that may come. The city is lit up green and red, and street performers fill the streets with the sounds of Christmas.

If you are anyone like my husband and me, you will have guests visiting you who might like to step outside of your house during this time of year. Post gift wrapping and unwrapping, ice-skating in Millennium Park and the SkyDeck tour, you may feel like you’re coming up short on other fun activities to do with your guests. Worry no more! Here are some festive ways to make their stay in Chicago unforgettable.

Brunch at The Winchester

Like most Chicagoans I am an avid fan of brunch, and there are plenty of options to choose from. However, The Winchester is a local gem I had to share with our guests. Breakfast here is fresh, tasty and proportioned just right so you feel like you’re getting the perfect amount to start the day. It has a really comfortable and simple décor that will leave you feeling extra cozy. I stand by the seasonal quiche, but if you’re looking for something on the sweeter side, the waffle is delicious. You will certainly give your guests a taste of what brunch in Chicago is really like with this favorite.

Pie at Hoosier Mama Pie Company

Chicago does sweet treats pretty well, so naturally I recommend trying as many as you can with your holiday guests. And if you have limited time and can’t try them all, remember that Hoosier Mama Pie Co. will always impress. They’ve put their own twist on traditional pies, and their Chicago Avenue location is the perfect spot to cozy up after a day of exploring. I recommend the Hoosier Sugar Cream and Chocolate Chess, though I’m certain every pie they serve is a crowd pleaser.

CTA Holiday Train

When I first moved to Chicago, I boarded this train on accident only to be pleasantly surprised with the best CTA trip I ever had. Truly amaze your guests by taking them on this one-of-a-kind ride as you venture out to see Chicago. The outside of the train is worth taking photos with (See the photo above to learn that Santa is definitely up for a selfie), but the inside is beyond amazing and full of Christmas joy. Santa and his elves ride the train, passing out candy canes and season’s greetings, while the interior is decked out in green and red. Your visitors will fly home wishing they could take the Holiday Train instead!

ZooLights at Lincoln Park Zoo

One of my favorite holiday events to take out-of-towners to is ZooLights. Not only is every tree decked out in sparkling lights and displays, but it is free to attend! You can see the many lighted displays and twinkling lights while also having access to different animal houses. Stay warm by grabbing a cup of hot cocoa or mulled wine and enjoy the holiday festivities. On your way out, stop to see the skyline and grab a photo of your guests for next year’s Christmas card!

Local Markets and Holiday Fairs

Visitors and locals alike will need to get some Christmas shopping done. What better way for your guests to see what Chicago has to offer than through local holiday markets? Artisans and DIY crafters will be out at fairs such as the Renegade Craft Fair, Bitter Betty Bazaar and the Made in Chicago Holiday Market this month, selling goods that you either can give to a loved one or suggest as a Chicago souvenir.

Emporium Arcade Bar

We took our Thanksgiving visitors here for a last hurrah in the city and had a great time grabbing a drink and battling over shuffleboard and air hockey. There are two Emporium Arcade Bar locations, both in exciting areas where you can grab a quick bite to eat beforehand or do a bit more holiday shopping. Your trip to this arcade will be a great way to wind down after a busy week of sightseeing, and hopefully your guests will be booking their next Chicago adventure before they even finish the first!


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