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By now you have probably chosen a bae to snuggle up with this winter. As some Chicagoans gear up for the cold weather in the city of wind, here are 5 places to take your bae during the holiday season to keep you two from going stir-crazy.

1) Santa Baby at Deuces and the Diamond Club

3505 N Clark St, Chicago, IL 60657


If Christmas is your favorite time of year, you need to hit up Santa Baby at Deuces and the Diamond Club. This over-the-top Christmas bar in Wrigleyville offers some of the best Christmas themed drinks and satisfies the kid in you with all their Christmas decor. This is a great place to take Christmas pictures with your significant other as the pop-up bar offers 10+ holiday photo ops. Santa Baby runs through January 16, 2023. Log onto to get your tickets.

2) Elf’d Up

3485 North Clark Street, Chicago, IL 60657


This pop-up bar inspired by the 2003 movie Elf stands out compared to the Christmas themed pop-up bars throughout the city. The bar is decked out with more than 1,000 decorative elves, Christmas trees and colorful lights. If you have a sweet tooth this is the place for you! There are tables flooded with candy, candy and more candy!! If you’re into trying new things Buddy’s breakfast pasta is a dish like no other, spaghetti with maple syrup, chocolate fudge, syrup, marshmallows and strawberry frosted pop tarts. If vibes are what you’re looking for you can skip out on the pasta dish and try one of their Christmas drinks. Amongst the Elf decor and sweets for your sweet tooth, the pop-up has trivia night and merch giveaways on Mondays. If you would like a photo-op with Buddy himself, you can swing by Thursday to Sunday. For more information log on to

While some single parents and couples with children may not be able to get a sitter there is no sense of canceling date night and letting the kids drive you crazy in the house. Here are a few places you can take the kids while also enjoying yourselves as adults.

3) Jack Frost Winter Village

1455 N Elston Ave, Chicago, IL 60642


Jack Frost Winter Village is a family favorite and a one stop shop for fun and all things Christmas. From inner tubing, ice skating and bumper cars the kids will have a blast. For the adults, you can warm up at one of the multiple bars onsite and grab a Christmas themed drink. Need a tree? head over to the Christmas tree farm. Looking for a place to get a few family Christmas pictures without having to hire a photographer? They also have multiple photo-ops. Jack Frost Winter Village runs from December 3rd-January 1st. For tickets log onto

4) Light Up the Lake at Navy Pier

600 E Grand Ave, 60611


Light up the lake has seemingly taken the place of Navy Pier’s beloved Winter Wonderfest, although Light Up the Lake doesn’t have as many attractions as Winter Wonderfest, the attractions include an ice-skating rink, Santa Clause house as well as an interactive light show through Winter Wonderfest Forest. Light Up the Lake runs through January 7th. For tickets log onto

1060 w Addison

5) Winterland at Gallagher Way

If you’re looking for a vibe similar to Navy Pier’s Winter Wonderfest, Winterland at Gallagher Way is where you need to be. Aside from the Kringle Market that greets you upon arrival, there are several attractions once walking into Wrigley Park. From the huge ice-skating rink to winter tubing and bumper cars, there is something for the whole family. Winterland at Gallger Way costs just $5.00 to enter with add-ons ranging from $10.00-$69.00. For tickets log onto

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