Fun fact: I was born in Oklahoma and moved immediately to Chicago where I lived with my Granny until I was about four or five years old. I hadn’t returned again until my 21st birthday where I celebrated the weekend with my oldest brother. After this trip, I visited a few times a year until about 5 years ago. I haven’t been to Chicago is 5 years! After working with a hotel company back in September of 2021, I was connected with their sister hotel and guess what? It was in Chicago! So of course we had to do a Staycation. Since my husband was in training, I thought a trip for Ryann and I to Chicago would be so cool! Being able to take her to the place I lived when I was her age sounded like a great time!
Once the hotel reached out to me (oh, this is not a sponsored blog post by the way) I thought of what kind of trip I wanted us to have. Since we were still in the middle of a pandemic, I knew I wanted to do a sort of “Staycation” at the hotel instead of going out and doing much. FYI: I am aware of the definition of “Staycation” but I still wanted to call it that since we would be staying in. Luckily, we were able to do just that because the hotel had everything we needed!
Planning:
Since it would just be me and Ry, I was trying to think of things she would enjoy. My main focus for this trip was to put everything to the side and spend time with her. Ryann’s “thing” at the time was “I want to be a princess”. Basically, she wants to put on a big, pretty dress and wear it around the house. It was honestly the cutest thing ever!
So, I thought a luxury breakfast in bed at the hotel would be so adorable! We hadn’t watched Cinderella yet either so I figured we could also watch it in our dresses as well. If you know me, you know I am very last minute. Although this was my plan from the very beginning, I didn’t start looking for dresses until closer to our trip. Of course nothing would get to me on time or everything was really expensive. I was literally buying these just for our trip and figured we’d probably never wear them again so I didn’t want to pay an arm and a leg. After looking all over, I finally found a dress (which actually turned out to be a maternity robe) for me and a cute dress for Ryann. The way the two dresses matched was kinda crazy. LOL. Both of them are linked here.
The hotel planned to set up a S’mores board at one of their fireplace tables for us so I also wanted to get some cozy outfits which we ended up just wearing during the day. But how cute are they? (They’re from Fashion Nova/Nova Kids)
I check the weather prior to going and once I saw that it would be in the high 50s and even 60 one day, I decided we would plan to spend some time outside. I didn’t want to plan every single day because this was supposed to be a relaxing trip also.
Packing:
Once again, I procrastinate. When it comes to every thing especially packing for a trip. I think I like the thrill of having to rush to get things done. LOL. It was also my first time packing with a potty training toddler so I was lowkey stressed trying to get the products I needed. Are you a potty training parent or soon to be? Check out this blog post. There’s links to helpful items!
Since I would have to take a suitcase, stroller, car seat, and a potty bag, I had to plan out everything. I decided to use one suitcase for both of our clothes and check it. This allowed me to get around the airport a lot easier. While Ryann could have walked through the airport, I also don’t enjoy getting their super early (don’t judge me ya’ll lol) so I needed her in a stroller so that I could get around faster. Unfortunately I wasn’t able to get my travel stroller on time (we threw away her other one) so I had her big infant stroller. (10/10 do not recommend lol) It was definitely a lot but once I was able to drop off our checked bag, we were good to go!
Arrival:
Luckily, we didn’t have any stops. (I don’t think I’ll ever do a connecting flight with Ryann again unless I absolutely HAVE to. It’s just too much.) So we went to the bathroom before going to get our bags and headed straight to baggage claim. Ryann was learning her numbers at the time so I had her find the number of our baggage claim. (A cute little airport game to kid her entertained)
HIGHLY RECOMMEND: Doing little activities with kids while in the airport so they aren’t bored or going crazy if there’s a long wait.
Once we got our bags, we went to grab a car to head to the hotel. I hadn’t used Uber or Lyft in so long so I didn’t have Lyft on my phone. Our Uber went from $27 to $60+ in a 20 minute span. (Me taking Ryann to the bathroom, grabbing our bags, and coming back outside) I totally forgot about Lyft at first but that was the better option. *This is a reminder to check both before confirming a car. Our Lyft was about $27 while Uber was still over $60.
Once we got to the hotel, we checked in, put our bags up, and used the hotel’s shuttle service to go to Giordano’s. Because who goes to Chicago and not get deep dish pizza?
Giordano’s:
This was literally the only place we left the hotel to go to. I wish I had more photo but we were so hungry that nothing else mattered. LOL.
During Our Stay:
Ryann’s favorite thing then and now is Pancakes. So of course, we had to get pancakes. We set up to do a quick shoot, ate breakfast, and then watched Cinderella. I’m pretty sure we fell asleep soon after. It was a sweet time. If you don’t follow me on Instagram, check out this reel we made!
The rest of the trip was pretty relaxing and of course Ryann got everything she wanted from every one because she was the cutest small person at the hotel. LOL! Here’s the recap video of our stay! If you’re in near, or visiting this area, I highly recommend!
Tips for your Staycation:
- Get dressed when going to the hotel restaurant, just because! It’s cute.
- Make friends with the staff — they definitely look you out when you’re nice.
- Try to get a free upgrade, especially if you have Amex!
- Have a breakfast in bed photoshoot! Whether it’s luxury or in your robe/towel, do it! Especially with your kiddos, they’ll have so much fun!
- FORGET EVERYTHING ELSE. This is a time for fun and relaxation. Leave the work laptop at home, let your kids do whatever they want, have a glass or wine, and chill out!
Planning a staycation? I highly recommend it. And remember, technically a Staycation is staying at a hotel in your area so you don’t even have to travel. Whether you’re going with your boo, your kids, or yourself, plan it. Today!
Interested in more travel content? Check out my travel guides here!