Christmas Themed Dates in Chicago

Maybe it’s all of the Hallmark Christmas movies I have been watching, but if you ask me there is nothing like a Christmas themed date. I mean, any kind of date is great now that we have kids, but when there is chocolate, snow, and twinkling lights involved, it doesn’t get any better. Luckily for us Chicagoans, there are tons of different Christmas themed dates that fit any and all budgets. Read on for my tips on how to plan and enjoy Christmas Themed Dates in Chicago.

Photo courtesy Waldorf Astoria

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To me, one of the most romantic things my husband can do is take care of ALL of the planning for our dates, from making restaurant reservations to booking the sitter (and one day MAYBE he will even pack the kids’ overnight bags when they go off to Nana’s house!). So hop onto Open Table to book a table at some of Chicagoland’s most romantic restaurants, look into cool gift experiences in the area, or simply research Christmas Bucket Lists to figure out what you would like to do on your holiday themed date. Remember, the romance is in the details.


December can be downright FRIGID in Chicago, so be sure that you are dressed appropriately for whatever you are doing. Since most Christmas themed dates in Chicago are outdoors, remember to dress in layers, wear a warm (yet still stylish!) coat, and choose stylish and waterproof boots like these.

So many couples love to catch the CTA Holiday Train, enjoy some glogg at the Christkindlmarket, or simply look at all of the amazing Christmas light displays, but you aren’t going to be very fun on these holiday adventures if you are constantly talking about how cold it is. You can even gift your love an early holiday present from Moosejaw, which has just about everything you need to survive winters in the Midwest.


Traffic happens. Snow happens. And as the blizzard last month showed us, power outages happen, too. So go with the flow, be flexible, try something new if need be, and always remember that a bottle of red wine in front of the fire is always a good idea…even if the backup plan involved Hamilton tickets.


Photo courtesy of the Joffrey Ballet


Now that you have your sitter, your outfit, and a positive attitude—what to do on your date?!?! Luckily for you, I have some great suggestions. I was able to experience all of these events first hand so I can guarantee that you and your date will have an amazing time together.

“The Nutcracker” Presented by the Joffrey Ballet

I have to be honest about something…I’m not one who typically enjoys the arts. While I enjoy music and like to dance, plays and musicals aren’t my thing. But giant men crashing into each other at Soldier Field? Yes, please.

So when I was offered tickets to the Joffrey Ballet performance of the Nutcracker at the Auditorium Theatre, I didn’t have high expectations. Man on man was I wrong. Everything about the performance, from the engaging interpretation of the traditional Nutcracker story (it is set on Christmas Eve in Chicago, 1892 when the city was preparing for the World’s Columbian Exposition) to the dazzling sets and talented dancers was truly swoon worthy.

I guarantee that when Marie wakes up from her dazzling dream at the end of Act II, you will also feel that you woke up from the most beautiful Christmas dream.

You can buy tickets for the Joffrey Ballet’s performance here, and don’t forget to make either early or late dinner reservations (we chose the Gage on Michigan Avenue—delicious!) and spring for the souvenir cup so you can enjoy your drink in the theatre.

Photo Courtesy Chicago Trolley & Double Decker Co.

Chicago Trolley and Double Decker’s Holiday Light Tour

For those wanting to stop at some of Chicago’s most popular Christmas themed exhibits and enjoy the millions of lights that decorate the city, the Chicago Trolley and Double Decker’s Holiday Light Tour is perfect for you.

The two and a half hour long tour starts and ends at the John Hancock building and stops at the Christkindlmarket and Lincoln Park Zoo’s popular Zoo Lights. Each trolley is decked out with Christmas cheer, including festive décor and holiday music. All riders will receive ZooLIghts 3D glasses as well as a bag of Hot Cocoa CaramelCrisp from Garret Popcorn.

Our tour guide, Chris, did such a great job educating us not only about the architecture while we drove through the city, but also shared stories about Christmas in Chicago that I didn’t know about before–and I even taught a class on Chicago history so that’s saying something!

The trolley runs every night up until Christmas Eve, with tours starting at 5:30 p.m. Be sure to dress warmly, wear comfortable shoes, and bring a lightweight camera so you aren’t bringing around bulky electronics (guilty one right here—blogger problems!). Purchase tickets here.

Sippin’ and Strollin’ Through Lightscape

Brand new to the U.S. this holiday season, Chicago Botanic Garden’s “Lightscape” exhibit is the perfect spot for a date night. Its artistry is stunning and with different spots for spiked cider and Santa wine throughout the mile-long walk, it makes for a perfectly cozy Christmas-themed date. You can read my full review of Lightscape here.

Petit Holiday Market at the Waldorf Astoria

If you have been following my Instagram account, you know that the Waldorf Astoria is my favorite hotel in Chicago during every month of the year, but especially during the holidays. From their stunning courtyard and gorgeous Christmas tree, to the delicious finds at Café Margeaux, it is the perfect spot to get into the holiday spirit.

This year they are providing even more courtyard fun. Up until December 23rd, their courtyard is transformed into a Holiday Market that includes a mulled wine station, raclette station for grab and go sandwiches, artisan spiced nuts, and more. It doesn’t get better than the taste of France in Chicago–am I right?

Here’s to having the most festive and memorable Christmas Themed Date!

Have fun!
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    • Amanda says

      There’s just something magical about a Christmas themed date. It’s like we can pretend we are in a Hallmark movie! 😉

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