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Living Like a Local – The Guesthouse Hotel in Chicago

Let’s face it, traveling with small children is no walk in the park. From schlepping gear to dealing with picky eating, it can frankly, be a total pain the butt and result in less family travel time. But, it doesn’t have to be that way. Not when you visit the beautiful, family-friendly city of Chicago and stay at The Guesthouse Hotel that is!

The Guesthouse Hotel is a gem in the north part of Chicago, situated just south of the trendy Andersonville neighborhood’s shopping district. A section of The Guesthouse was originally built as luxury condos – and those finishes run through the entire facility, starting with the stunning lobby. Oversized leather couches, reclaimed wood doors and tables, and locally-inspired art that is meticulously hung in perfect order. Modern as it is, the space is entirely comfortable.

guesthouse hotel chicago family travel

The Rooms of The Guesthouse

Staying at The Guesthouse is not unlike having a wealthy friend who invited you to stay at their second home in the city, it is luxurious and comfortable. There are 1, 2, and 3-bedroom options, each with a gourmet kitchen and balcony. The South Building, has slightly larger rooms, a fireplace, and dining table. The North Building includes access to a private rooftop deck. All rooms continue the stylish, yet inviting decor of the lobby. We particularly loved the steam shower in our South Building room – what a decadent experience.

guesthouse hotel chicago family travel
Photos by The Guesthouse Hotel

Awesome Amenities

So, the space is nice, but what about everything else? Well, that’s what will set this apart from any other places you’ve stayed and will change the way you travel with your family (or any large group) forever.

Prior to our visit, The Guesthouse reached out to us to see how they could stock us up. We pre-ordered wine, beer and bourbon because we knew we would be dining out mostly, but you can order food delivery (for those picky eaters?) and they will stock you up before your arrival. You know how it is, you travel all day, you get to where you are going and little Timmy is dying of hunger. Hello pre-stocked kitchen in a fancy hotel. Genius. Not only is it uber-convenient, it makes traveling with the family SO much easier! And, of course, they have all the pots, pans and dishes you need in order to make it feel like home.

But, wait! It gets better. No need to schlep the kid gear. They can ALSO stock you with just about anything you need in that category, too – they have cribs, bouncy seats, high chairs, car seats; they also have kid utensils, and family games, too. (I must also mention, they are also dog-friendly and can stock you up on things for Fido, too!)

guesthouse hotel chicago family travel

Local Excursions in Chicago

Now that much of the hassle of family travel has been taken away, it’s time enjoy the city of Chicago with your family! The Guesthouse Hotel is in a great location – you can hang out in Andersonville with many shops, restaurants, and parks a 2-minute walk away, or you could catch the L Train to the downtown area, with the nearest station being about a 5-minute walk.

You can also do the bike-share thing by renting city-wide Divvy Bikes (we did this and had a blast!). It’s super easy to get nearly anywhere between the train, Divvy Bikes, Cab or Uber, or even your own car (don’t forget, The Guesthouse has car seats available).

Here are a few things to do with the kids in downtown Chicago:

  • Visit the Zoo – it’s free
  • Go to Millennium Park – home of the “Bean”
  • Hang out at Navy Pier – home of a cute, little amusement park
  • Take a Boat Tour – most tours close out by mid-October
  • Spend some time sightseeing – it’s a beautiful city!
  • Go to the Museum of Contemporary Art – there is a great kids room

chicago family travel

You will not be disappointed when you take the family on a getaway to Chicago. So many fun things to do in such a great, family-friendly city.

No matter what you end up doing when you visit the Windy City, you can live and feel like a local when you stay at The Guesthouse Hotel.


Special thanks to the The Guesthouse Hotel for hosting my stay. All opinions are my own.




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