When I applied for the Chase Sapphire Preferred card in November, there was a sweet sign-up bonus that included $300 credit toward purchases on their travel portal. I don’t typically book travel that way, so I brainstormed what we could use it for. We ultimately decided to take the kids for their first overnight stay in Chicago!
My husband and I were both born in Chicago, ultimately moving to the suburbs as kids, though I returned there for my college years. Growing up in and around the city, we definitely have a special place in our hearts for Chicago, so I’m always excited to introduce our kids to new and exciting parts of it!
Here’s everything we saw/did and how the kids liked it:
L7 Chicago
For our hotel, I picked L7 Chicago by Lotte for a very specific reason: the rooms had extremely sweet-looking window seats! I thought the kids would get a kick out of it, but I didn’t expect them to spend every waking minute in the hotel playing in the window nooks (which they did). They’re super cozy and unique – and we loved the river view. The hotel has been the number one thing the kids have talked about since our adventure, surprisingly 🙂
We also found that the location was perfect for our needs – short Lyfts or walks for everything we wanted to do. Additionally, there were nice little extras, like sheet face masks in the bathroom and an in-room air purifier, and free toiletries available at the front desk for my husband who forgot his toiletry bag and free coffee in the lobby in the morning.
Maggie Daley Skating Ribbon
Our 6 year old has taken a couple sessions of “learn to skate” at the local rink, so we thought he might enjoy checking out the Maggie Daley Skating Ribbon. The day before our visit, I visited the website and slightly panicked because 3 of the time slots were already filled. I quickly grabbed the 5-7 pm slot, a little bummed that it would be dark and presumably cold by the time we were out there. When you book your ticket, you indicate whether you need to rent skates or not, because you pay much less (or nothing, depending on the day of the week) if you’re not renting.
We took a Lyft to the skating ribbon, checked in, rented a locker, then laced up! I loved the skating ribbon. Looooved. I’ve done open skating at rinks, but it can be kind of monotonous going around in circles, so this was way better than anything I’ve tried before. And, honestly, it ended up being kind of amazing to be in the later time slot because you could really see all the festive red and green lights of downtown, so it all worked out!
After our first lap, we rented a snowman ‘pusher’ for our 4 year old to try out, and later we grabbed some hot chocolate from the cafe located along the ribbon. Everything was pretty great – this attraction got two thumbs up from each kid.
JoJo’s Shake Bar
After a short rest at the hotel, we ventured out to dinner at JoJo’s Shake Bar, which was a recommendation from a friend. They had an awesome pop-up winter wonderland, which you see right as you check in. The kids had fun taking a look around and getting some pictures together while we waited for our table.
I fully expected the kids to get one of the crazy milkshakes with cookies and stuff poking out of it (imagine a kid version of a Bloody Mary, haha), but they opted for a surprisingly reasonable Oreo shake along with dinner. We all enjoyed our food and the shake really was pretty incredible!
This was our last stop for day 1 – we made the easy walk back across the river to the hotel and just relaxed before going to sleep.
Christkindlmarket
You know, I knew I wouldn’t like the Christkindlmarket (lol), but I thought I should give it a try for once in my life in case the tiny boot-shaped mugs won us over. We decided to walk over and pop in right when it opened, to avoid crowds. We got there 3 minutes after it opened and it was already packed! We made one very slow lap through, bought 3 macarons, and made a run for it. All of us agreed, sadly: two thumbs-down on the market.
Macy’s window displays
After the Christkindlmarket was a bust for us, we walked back to our hotel, making sure to pass the Macy’s windows. It was fun to see the window displays and the decorative trumpets. We also liked going by the ABC studio, where we could see the news being filmed. Nice, free detour that is worth checking out for sure.
Museum of Science and Industry
Next, we checked out of the hotel, grabbed our car and drove to the Griffin Museum of Science and Industry. The drive is nice, along Lake Shore Drive, and pretty fast. We were able to easily find free parking on Stony Island Ave.
Quick money-saving tip: check your local library for coupons for museums! We were able to save $5 per ticket using our library card through the Explore More Illinois program.
MSI was on the agenda for our holiday visit because they have a Christmas Around the World exhibit that sounded really cool. There’s over 50 trees, each decorated to display the traditions of different cultures. I would’ve wanted to check out every tree, but the children didn’t have the same patience I did, so we made sure to find the ones that were special to us before exploring other parts of the museum.
We were able to check out almost all of the free exhibits, with the plane display being a particular favorite!
Overall?
We had so much fun. I didn’t know how the pumpkins would do with the cold, but they were troopers and we had the best time exploring. Chicago really is so magical around the holidays, and it was even more special for me to share my favorite city with my littles! Can’t wait for our next city day!
