Three Days in Chicago

by | Jun 23, 2021 | FTM Travel Info

My husband and I have traveled a lot with our 5- and 6-year old daughters, Sydney and Payton, but our trips always seem to revolve around Walt Disney World or outdoor adventures. Five trips to Disney since April 2018, hiking and skiing in Colorado, a 14-day road trip to the Grand Canyon, Gulf Shores beach trips (a short 5-hour drive from our home in Birmingham, Alabama), hiking in the Pacific Northwest, camping in the Smoky Mountains, numerous trips to my home state of Nebraska, and my husband’s home state of Georgia.

Rewind to September 2020. My girls were in virtual school due to the pandemic. One of Payton’s assignments was to write a nonfiction chapter book. My art-loving-momma-heart jumped for joy when she decided to title her piece “Famous Works of Art and Artists.” Hence, began her love for the artist, Vincent VanGogh.

Fast forward to April 2021. I was browsing through a copy of Midwestern LIving Magazine with Payton, when she noticed an advertisement for an “Immersive VanGogh Exhibit” in Chicago. She quickly (and LOUDLY) proclaimed, “MOM! I HAVE TO SEE THIS!!”

Hmmmm…little kids, big city. Can we do this? Are we ready for this type of trip? YES!

I absolutely LOVE Chicago, and was excited thinking about all the places we could take our girls! I started planning, and shortly after, we landed at Chicago Midway International Airport and the urban adventures began!

Planning “Big City” trips with kids requires a lot of thought. Picking the right location to stay. Deciding how to travel (public transportation, ride shares), how to pack car seats, and what type of car seats. How much to take and what to pack. Timing meals and ticketed events to allow enough time to get from place to place. So many things to think about!

This is where being a travel agent came in handy. I love planning. I love taking all the little puzzle pieces and making them fit together to form the perfect trip. I love researching what activities to do, things to see, food to eat, and what local experiences we need to try.

I have traveled to Chicago by myself many times, but this was my first trip with kids. Here are a few tips that made our recent urban adventure a success…

#1: Pack light!

Would you believe I packed everything for both of my girls and myself in a small carry-on suitcase and backpack? I did not want to check a bag, and I also knew I did not want to be schlepping lots of luggage on public transportation. I am a notorious overpacker, but was conscious this time to take minimal makeup/skincare, utilize the hotel shampoo and conditioner, and went without the curling iron. It was a ponytail all weekend for me!

#2: Put your outfits on repeat.

You can wear an outfit more than once! With that said, I like a clean shirt for each day, but I always wear pants more than once! I have fallen in love with the Vuori Wayfarer Pant. They are lightweight, super comfortable and can be easily washed in your hotel room and hung to dry overnight if needed. Best of all, they can be dressed up with a pretty blouse, or styled casual with a T-shirt. Versatility at its best!

#3: MiFold Booster Car Seats for the WIN!!!!!

Gone are the days of having to tote around heavy, cumbersome car seats! MiFold Booster Seats made using rideshare transportation a breeze! Bonus–the seats fold up so small that I could easily fit two in my backpack! It is a good idea to research what transportation options are available for your destination. If you will be taking a car, make sure to have appropriate safety seats for your kids. Don’t want to buy a new travel car seat for a trip? Ask your friends! I’m sure someone has one to share!

#4: Know your kids.

Are they night owls? Are they early birds? Do they need a break in the middle of the day? Keep some of your daily routines as part of your travel routine. We usually have “quiet time” in the afternoon. At home, that means reading or watching a movie. On the road, that may mean eating a late lunch and sitting at the restaurant for an hour, or enjoying a sweet treat in a cool ice cream store and getting off our feet. And some days, like on this trip, we went back to the hotel one afternoon and had a movie break. We couldn’t miss the release of Disney’s Luca on June 18th!

#5: Experience the city as a local!

We live in Birmingham, Alabama where public transportation is not a part of our everyday living. We took full advantage of public transportation in Chicago, and it was fun to see our girls’ reaction the first time they heard “The El” coming through the tunnel!

Ask around! Ask friends and family who have lived in, or been to, the area you are traveling for recommendations on places to eat and things to do. The first thing we ask when checking into a hotel is always, “Where is your favorite place to eat?”

#6: Buy tickets in advance.

In order to keep visitors safe, many museums and attractions are still operating with limited capacity. Be sure to purchase tickets in advance when possible! The same goes for dining. Check to see if restaurants require reservations. Many times you can book days or weeks in advance! This is a good idea, pandemic or no pandemic.

#7: Be flexible. 

The weather may change. A child may get tired or hungry. You may be worn out! It’s okay to shift or flex your plans as needed. Think of an itinerary as a road map. It’s simply a guide. There are always other routes, or other ways, to enjoy your destination.

#8: Managing Souvenir Expectations.

How do you handle your children wanting EVERYTHING when they go on vacation? We set our souvenir expectations before we set foot out of our house. One option is telling them they can pick ONE item to purchase on the trip (within a certain budget). When they find something they think they want, ask them,  “Can you live without this?” Remind them this is the ONLY item they will get, and see how they react. Another option is to give them a set amount of money for the trip. This is a great way to teach concepts of budgeting and counting money!

#9: Pick One.

Sometimes being away from the comforts of home can be hard on little kids. We allow our girls to pick one “stuffy” they can bring on the trip. We always attach a tracking device, such as the Apple AirTag to ensure we don’t lose a favorite toy on the road!

#10: Enjoy!

Your trip is not only fun, but educational. You are showing your kids there is a world of adventure for them to explore. So relax, have fun, and ENJOY!