Best Friend’s Trip- Make it a yearly thing!


The mom guilt was strong at the beginning of planning this trip, and I am SO glad that it didn’t cause me to pause or postpone this adventure. It was a best friend trip for the books!

We started planning this at the end of summer, knowing the long winter months would be a great time to have something to look forward to. Originally looking to go some place warmer, the cost and overall time to fly somewhere had us looking a bit closer to home.

While not warmer, Chicago seemed like a great place to get away to. To explore and feel more “big city” while connecting and letting loose. While we had moments of “aww the kids would love that play area” we were able to really escape and focus on things that fill our cups. To laugh, drink, eat and be silly without the need to stop and change diapers or lug a bunch of kids supplies with us. No need to clean up the air BnB after kids (or a husband) and to just be in the moment.

Don’t make too many set plans

We kissed the kids and husbands goodbye on a Friday afternoon and hit the road. In 3.5 hours we made our way into the city and into our Air BnB. We made loose plans so that way we didn’t have the typical daily pressures of being on a schedule. We knew 1 daily thing we’d like to do and went from there.

Friday night was a Piano Bar to have a drink after dinner and listen to some live music. The Red Head Piano Bar came highly recommended. It did not disappoint.

Saturday we had a not so typical activity planned: tattoos! (This part may or may not be necessary for your best friend trip).  What made this event extra fun was it was an hour and a half walk from where we were staying. Sure we could have Ubered, but the walk not only gave us activity but time to bond, laugh and explore. We of course grabbed a coffee mid way.

After the tattoo we wanted to do more exploring. Hit the typical touristy destinations: Millennium Park and Shopping on Michigan Ave. We naturally chose to walk some more.

Don’t be afraid to use your legs

That adventure took us to discover the Navy Pier. Something we didn’t even have planned. The water was such a pretty blue, we were super happy to have made that detour. Way different from the Lake Erie and Maumee River we have nearby.  That led us along the river and back up to the hustle of the city.

Naturally along the way we found some local treats and hidden gems. We walked a total of 15 miles on Saturday! You guys, Disney’s Magic Kingdom only gets you 1.2 miles.

We finished our night with a planned stop for an Espresso Martini at the Starbucks Reserve Roastery (highly recommend) and then dinner at ‘Ema’. (Another highly recommended visit given to us by a local).

While our 30+ year old bodies were a mess when we finished the night (I literally had to crawl around the floor in our place by nights end) it made for such a good laugh and story to bring home with us.

The plan was to finish Sunday with brunch and head home. But we had had so many good times already, we packed it up and headed back to our little monsters that we were of course ready to see.

While we do have so many amazing things here in our local area, getting away for a quick trip, where we didn’t have to be responsible for others, was such a mental win and mental need for us both. It allowed for 2 people that talk every day, to connect in a different way and create some fantastic memories.

Our goal is to plan a trip each year to a new place. To end the trip we are on with ideas for the next trip. So tell me, where would you plan to take a long weekend for your next (or first) best friend trip?


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