Chicagoland.
One of our favorite winter past times is visiting Chicago in the winter. We havent visited in several years, and thought it was time to return to the city for some fun.

We tend to venture to the woods, or camping, or hiking when we go on family trips, but one of our favorite big cities is Chicago. It’s only around a three hour drive from home, and it just feels like tradition to visit at Christmas. Ian and I started doing this before we had kids, and have fond (somewhat) memories of pushing our babies around in a stroller through the snow many years in a row.

This year felt different, the boys are bigger, we didn’t have a stroller, and it was just a lot of fun.

Whenever we stay in Chicago our first stop is checking in at the Kimpton Hotel Monaco. We have always loved Kimpton hotels because of their attention to detail and coziness. Kimpton hotels are generally boutique hotels, so they are smaller, and they really cater to their guests. They offer hot cocoa bars, wine receptions in the afternoon, and often times you’ll get a little surprise in your room if you are a repeat guest. This time we got a bottle of wine upon arrival!

We highly recommend looking for a Kimpton if you’re visiting a big city.

Photo above of my attempt to embarrass the boys by taking a hotel lobby pajama photo. They were good sports and did it for their Mama.
Photo below of the window seats (beds really, Greyson J sleeps here) that we just LOVE in the corner suite.

Another must do on our list in Chicago is Maggie Daley park, and the skating ribbon. The boys have always loved this park, ever since they were little. Skating has become a bigger part of our lives in recent years, as we have a die-hard hockey player in our family. Most of us don’t get on skates very often, but we’re always at a rink.

Visiting the skating ribbon at Maggie Daley Park is something fun we can all do together. I highly recommend reservations online, as it will get busy and does sell out the week before Christmas. Bonus if you bring your own skates, you don’t have to wait in line to rent them. However, getting there early there we noticed there was no line for rental.

Skating at night time under the lights, with the perfectly timed falling snow was so much fun.

The playground at Maggie Daley is lots of fun in the summertime. It was a little challenging in the winter with all of the ice and snow, but Ethan still promised Greyson he could visit “the biggest playground in the world” so we had to stop and play a little here too.

Other favorite stops included Cloud Gate for photos in front of the bean, pizza for dinner at Giordano’s, Macy’s on State St. for a little Christmas shopping, and Starbucks Reserve, the largest Starbucks in the world!

If you’re after a weekend getaway, or just a night away in the city, Chicago can be really fun for a family. Let us know your favorite thing to do in the windy city!