Packing for a Weekend Family Getaway- Chicago edition

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My favorite big city to visit every summer in the Midwest is Chicago and it’s only gotten sweeter since the arrival of my children. And since Anakin was born, there’s been many changes to the city to make it more family friendly oriented. Like the recent addition of Maggie Daley park- a big (free) playground for children (and the child inside us). We look forward to visiting Chicago every summer and this year we have planned for a day in the Windy City and then the other two days around the area. It will also be our first time traveling with a baby and as a family of five. So being the planner that I am, I’ve been brainstorming every little detail about this trip and writing it all down so that I don’t forget something important. Here is how I plan and pack for a weekend family trip.


1 month before: Book your reservations if you don’t plan on staying with family or friends. I usually book my hotel stay through and find the app very user friendly.

2 weeks before: Start gathering sight seeing ideas and reading reviews. What are the top attractions and when will they be open, etc. Also, purchasing tickets ahead of time could save you a few bucks and skip waiting in line. I know Chicago has a CityPass where you can visit 5 of the top city attractions at a discount and the best part, you get to choose and it’s good for up to a week!

1 week before: Finalize your day to day plans and start gathering items on your checklist.

2 days before: Go shopping for items that you need on your checklist as well as snacks or drinks for the trip. Pack all your snacks into smaller units for the kids using sandwich bags or small ziplock bags. If you’re getting there by car, make sure your car has been checked and ready to go. Have your car kit ready and a safety kit in place in case of emergencies.

The day before: Packing day! It helps to check the weather where you’ll be going and pack according to that. This time of year in the Midwest, it could get muggy or it could be raining. So I pack lightweight clothes that can be layered. I also pack more accessories than usual because sunny days usually mean you have to protect your skin more. So I pack hats and sunnies in addition to the usual jewelry. I also don’t enjoy wearing sneakers although it is the preferred shoes for walking but, my feet get so sweaty that I prefer sandals. Pack your diaper bag making sure to check off items on your checklist as you go. Also make sure you have your first aid kit in your diaper bag. Put your diaper bag next to your luggage so you don’t forget to pack that in the car (we’ve forgotten the diaper bag a couple of times while going out of town and it was hectic!). Put all of your snacks in a small container and drinks in a small cooler. Be sure to freeze your bottled water overnight so you won’t have the need for filling the cooler up with ice. Make sure your car is gassed up. I always bring a few empty plastic grocery bags as trash bags for the car. Have your paper maps, itineraries, and tickets printed out and put in your luggage.



For the Kids
3 outfits: top, bottom, underwear, socks

  • 2 pairs of pajamas
  • 2 pairs of shoes
  • a hat/headwear
  • sunnies
  • swimsuit
  • towel
  • wash cloth


For Baby

  • 4 outfits
  • 2 pajamas
  • 2 hats/headwear
  • towel
  • washcloth
  • baby wash shampoo
  • babywrap or sling
  • diapers, wipes, butt cream
  • stroller


For Everyone

  • first aid kit
  • snacks
  • drinks
  • wet bag/laundry bag
  • shampoo, conditioner, body lotion, aloe lotion
  • toothbrush, toothpaste, floss
  • camera and accessories
  • paper maps, itineraries, tickets

TIP: Pick outfits to wear based on the activities you’ll be doing. For example, Ruby’s outfit while traveling was a dress. It’s easy to just hike up if she were to potty and easy to take off and put on after getting wet at the pool.

I hope you found this post useful and let me know where you plan on going for your summer weekend trip?!


At the Milwaukee Zoomzoo1mzoo3

At the Thomas Day event in Union, ILthomasday1thomasday2


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