Winter Chicago guide with kids

There is something so magical about a big city during the holidays. As many of you know we spent a decade in the windy city. It's where Michael and I met, feel in love, got our first jobs, got married, and had a baby! Wow talk about lots of big moments we've had in Chicago. So naturally Chicago holds a special place in our hearts. With the drive being around 4 hours (sometimes 5 with these guys) from Detroit we like to make the trip back as much a possible. The holidays and winter time still has lots of fun things to do in the city. Here's our speedy weekend broken down for you!

where to stay

We're all about living local. So naturally VRBO & Airbnb speak to us! Staying just outside the heart of downtown (literally 1 - 2 miles) also drops the price. Plus Chicago neighborhoods are amazing.

Airbnb with kids in Chicago
Airbnb Chicago winter travel

what to eat

Authentic food. This is something I totally miss about this city. You can get real authentic food in every part of the city. This trip we decided on Greek, Spanish tapas, and Italian (of course)!

WhereAthenian Room. I seriously dream about this little gem in the heart of Lincoln Park.

What we had: Taramosalata (greek caviar), Chicken kalamata style with a greek salad and greek fries, and gyros. Kids had: everything we did. Zo loved the gyro meat & pita. Zig loved all the carbs & a few pieces of chicken!

Best Greek Food in Chicago
Greek Restaurant Chicago
best Greek Restaurant Chicago

Where: Bulerias Tapas Bar. This place is legit. Every time we go here it's like walking back through the streets of Spain. Plus it's located off Ashland for easier parking and it's got a great vibe for kids.

What we had: Pan con tomatoes, patatas bravas, empanadas de queso, chorizo espanol, empandas con chorizo, datiles, salmon ahumado, gambas al ajilo. kids had: what we did but the patatas bravas needs the sauce on the side because it's 🔥🔥🔥

Where: PR Italian Bistro. Formally known as pizza rustica and seriously good Italian food! 

What we had: First for the antipasti: polenta and charcuterie. On to the insalate: rustica and caesare. Last risooto ai porcini, raviolacci costexine, angnolotti aragosta and tutta pizza. kids had: pepperoni pizza

Best Italian in Chicago
Chicago Pizza


Where: Walnut Room. Talk about magical, especially during the holiday season. The tree is amazing and you get to look out at State street. The one down fall is you can't make reservations, but Michael always gets us in quickly. He seriously has a gift.

What we had: Wisconsin Cheese Platter, Lobster Bisque, Walnut Room Salad, Oven-Baked Meatloaf and Caramelized Salmon. kids had: butter noddles and grilled cheese.

Chicago's Walnut Room at Christmas


Where: Sweet Mandy B's. This is by far my absolutely favorite sweet place in Chicago.

What we had: Cupcakes! We love their classic yellow cake with buttercream frosting, although all the cupcakes there are amazing. kids had: Cupcakes too!

Best Sweets in Chicago

what to do


Where: Southport Corridor

What to do: Chicago is full of shopping options. But the local boutiques are always my favorite😊

Where: Michigan Ave

What to do: I'm sure you know there are lots of shops on Michigan Ave. But I like to hit up the ones I can't find in Detroit (Zara, Uniqlo, Crate & Barrel - ok yes we've got one of these but this store is just amazing)

Chicago Shopping with toddlers
Chicago in the winter with toddlers


Where: Any Chicago Park
Chicago is full of amazing parks & let's be honest with kids they are fun any time. We stopped by Oz Park for all kinds of fun.

What to do: Bundle up and get out. Fresh air and play time is always a good idea.


Where: Lincoln Park Zoo  

What to do: Zoo Lights. Walking though the zoo is truly amazing with lights, music and all kinds of goodies to keep you warm and full! Once you've seen this light show you won't want to miss it! Dress warm and head there early as parking by the zoo is difficult and you want your little to be able to enjoy the lights. Good thing Chicago gets dark around 4:00.

Chicago Zoo Lights

Where: Holiday Market 

What to do: This is a traditional German American Holiday Market. It takes you right to the streets of Germany, but the only problem is on the weekend it is absolutely packed! We could barely move with our kids there. I recommend going during the week.

Chicago's German American Holiday Market
Chicago's Holiday Market
Winter Travel in Chicago with kids

Where: Macys on State Street

What to do: Head downtown and check out the windows & sights inside the store including santa!

Macy's in Chicago
How to travel with kids to Chicago in the winter

Hope you have as much fun in Chicago as we do!

much love-



Chicago Holiday travels with kids