Our Chicago Winter Bucketlist

January 9, 2020

Winter is here in Chicago. Sigh. I read somewhere that the Farmer’s Almanac is predicting there will be another Polar Vortex Part 2. I am so NOT ready for that! Being inside all winter long is so hard, especially with kids. The boredom is REAL. With all the being said, I put together a Winter Bucketlist to help us Chicagoans get through this winter together. Haha.


Happy hour at Homeslice

We recently went as a family to the happy hour at the Lincoln Park location and it was so much fun! The deals are great and there are FREE games to play. Noah loved it. So much, Mila went home and Noah and I stayed to play some more. There’s no kids menu, but the pizza slice is HUGE and perfect for two kids to split.

Plus lots of grammable opportunities as well.

Aster Hall

We did this during the first Chicago snowstorm we had on a Saturday night. We walked around the mall, which was pretty empty at the time. There was lots of room for Noah to run around, there is a family restroom and lots of dining options. Plus, a bar with lots of desserts. Then we did some shopping after. Kind of a win win for everyone!

Timeout Market Chicago

I love this food hall! Some of the best chefs in the city serving up great dishes BUT they have an entire upstairs area for events. And to my suprise, they have a lot of kids events! Story time, pasta making classes and more! I would check out their Instagram or website for more details. We plan on going to story time real soon!

Brooklyn Boulders

I will be going rock climbing here in a few weeks and I am excited try it out. I heard it’s a super hard workout, but fun! To my surprise, they have a TON of classes and programs for kids. After school programs, classes, birthday parties and more. There is a location in the West Loop and they are opening at Lincoln Park location in the next few months!

Update- I went to the intro to climbing class and loved it! It’s such a good workout and the instructor explains everything. Highly recommend if you are looking for something to do indoors! There were lots of kids around too.

Winter Carnival at Eagle Ridge Resort

Ok, ok, I know it’s not in Chicago, but it’s just 3 hours away and this sounds like such a fun family outing. We did our babymoon at Eagle Ridge and had a nice escape from the city. It’s so relaxing, but there are lots to do at the resort and in the area if you bring the family. This carnival would make a great winter escape for everyone.

It would make a nice getaway for a parents weekend away too!

Eagle Ridge is a nice escape from Chicago and there is a lot to do while visiting. Perfect getaway to add to your bucketlist.
Trails around Eagle Ridge Resort
Altitude Trampoline Park

I have been wanting to do this trampoline park for so long! Has anyone tried it? I’d love to hear how it was. They have Toddler Time for ages 2-6, which is perfect for us. It’s definitely on our list this winter. Noah will LOVE it.

The Kids’ Table

This is a cooking school just for kids 18 months and older. I have always wanted to bring the kids because it looks so cute! They have weekday and weekend classes as well as private parties. There are two locations in the city.

Museum Free Days

There a ton of FREE museum days coming up this winter. They do get SO SO SO crowded, so I recommend going really early or later in the day. We did Noah’s 3rd birthday party at the Shedd last February and it was so much fun! He loved it.

LEAP: Learn, Explore and Play at Lincoln Park Zoo

I did this class series last winter with Noah and brought Mila with, who was a newborn at the time. He loved it! It’s a class full of music, sensory activities and it ends with a read aloud. You can read about our experience here. They have weekday and weekend classes available.

Family Movie Night at Broken Barrel

Some of the best wings in the city (that and Bird’s Nest!) and now on Mondays and Wednesdays they will have a movie night for the family. Plus, KIDS EAT FREE!


We went bowling with both kids a few months ago and honestly, we had the BEST time. Honestly, I thought Noah might be too young, but he loved it. Many places have have bumpers and lighter balls for the kids. We went Kings Bowling and had a great experience. Plus there are lots of games we played and the food was delicious. There’s a Lincoln Park and Rosemont location. I have also heard good things about Lucky Strike in Wrigleyville.


I have always wanted to try this indoor skydiving! It’s only for kids 6 and older, so we have some time for it. There are 3 locations in the Chicagoland area, in the city and two in the suburbs.

Date Night

5 for 5 at Whole Foods

On Fridays, at select Whole Foods, there is a wine tasting paired with small bites. Manny and I have been doing this for years, even before kids. It used to be $5 dollars for 5 pours and tastings and now it’s $10 (sigh), but totally worth it. It does get crowded, so I recommend getting there right at 5pm. Once you are done with your tasting, you can pick up something to cook for dinner and buy your favorite wine you tasted!

We have also done this with kids, but would make an even better date night. I would call your local Whole Foods to see if they do this because I couldn’t find anything on their website about it.

Malt Row

I had no idea this even existed, but Manny did it a few months ago with his friends and loved it! There is a row of some really great breweries in Ravenswood. If you click on the link, you can see all of them there. I think this is a fun winter activity, food and drinking will warm you right up! Ha. Not all the breweries have food, but you can order from places which have deals with each location. If anyone does this, let me know how it is!


Honestly, one of my favorite things to do is go to Eataly and walk around with a glass of wine. They also have a happy hour with amazing deals and so many activities like cooking classes, wine tastings and fests. Check out their schedule for more info!

Happy hour at Eataly is something fun to do when it's cold outside in Chicago. You can grab a glass of wine and just wander around the store.
Leather leggings: Nordstromhttps://go.magik.ly/ml/ul57/ Rack // Leopard Cami: Nordstrom Rack // Shoes: Target
Shop 900 Golf Suite

I am not a golfer by any means, I think I have gone once in my life. However, this golf suite is SO much fun! I went a few months ago for their preview and had such great time. There are lots of other games like dodgeball and football to play. The drinks and food are from Astor Hall, so it’s all really good. Then you can go shopping around the mall after 🙂

Cooking Classes
Chicago Restaurant Week

I will admit we haven’t done restaurant week in a few years, but I think it’s great for trying new restaurants that you might not have normally gone on your own. In recent years, some of the restaurants have done “pop-up” theme which I think is something fun for a date night. It runs from January 24th – February 9th.



I had brunch here recently and loved it! The bar is beautiful and there are so many great tapas to share with large groups. They also have a large paella that would easily feed 3-4 people for $40.

Boqueria is a great place to go with friends for brunch.
Apres Ski Party at J. Parker

I haven’t done this, but how cool does this sound? For the 3rd Ski Season in a row, The J. Parker Rooftop is transforming into the largest Apres Ski Party outside of Aspen. The Roof will be open so sky attire is encouraged and they will have slopestyle cocktails. And it’s FREE. I will be there. Register here.

Curling at Kaiser Tiger

Kaiser Tiger has had curling for a few years now and I have wanted to do it with some friends! There is in person sign up only, unless you have a large group. You can contact them here to make those reservations.

Goat Climb and Yoga

Ok, Instagram kind of influenced me on this one. I have seen it pop up over all over and I want to try it! It’s a workout studio and one of their classes is goat yoga. This class and brunch would be such good date with your friends.

Rage Room

I did this with a group for my friend’s birthday and it was so cool. You can see me in full gear here. There are two options: you can bring in things or purchase items there to just smash the heck out of it. Then take turns in the room with your choice of music and just SMASH. We then went out for drinks and dinner after, such a fun girls night.

The Rage Room should be on your Chicago Winter Bucketlist. It's indoor, cheap and fun to do with friends!
Rage Room

What is your favorite? I would love to hear. I will try to update this every few weeks this winter, just to keep it current! You can find me here on Instagram.

Until next time,


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