We spent a few days in Chicago with the girls. We had an absolute blast, despite the big snow storm and winds that hit while we were there. With just about 48 hours in Chicago, we wanted to fit in as much as we could! I am excited to share our Chicago with kids travel guide!
Where we stayed
Hilton graciously hosted us at The Drake, A Hilton Hotel. We received their Dibs package, which includes insulated mugs with bottomless cocoa/coffee or tea, an exclusive savings passport to Magnificent Mile and more!
Our room was a suite on the 7th floor, with amazing views of Michigan Ave and Lake Michigan! It had an adjoining room with 2 beds for the girls. We often struggle with space in hotel rooms as a family of five, and had zero complaints here! There was lots of space for the girls to play, for us to relax, and so many windows – everyone enjoyed watching the waves crashing!
The location was amazing. Had the weather been better, we could have walked Michigan Ave, and done a lot of shopping! The Drake did have a few fun shops on the ground level, which are fun to walk through! On the ground level, you will find Chanel, Georg Jensen, Hildt Galleries, Mangel Florist (smelled amazing, and the flowers were gorgeous!), and a great little coffee shop called Lavazza Cafe that makes an amazing Chai Tea Latte! There’s also a little gift shop on the ground level, where Dave was able to purchase contact solution, without having to walking a block in the cold.
The staff was friendly, and a few bellhops completely made the girls’ day by calling them princesses each time we walked by. We ended up doing valet parking, just for the sake of connivence. It never took more than 15 minutes for our car to be ready from the time that we called for it.
Where we ate
We had breakfast at Café on Oak in The Drake. It was buffet-style, and really good. There was a huge variety – our favorite was the made-to-order omelette station. It had the cutest, almost beachy vibe, and surprisingly wasn’t crowded!
We braved the winds and walked the short 2 block walk from The Drake to Sprinkles for cupcakes. 100% worth it, although it was very crowded inside, and only had a few window seats – so don’t plan on eating there!
We had lunch at Shedd Aquarium, at Soundings Restaurant. It was very casual dining, which was perfect with the girls. We enjoyed burgers and the girls had chicken tenders and mac n cheese. We also had great views of Lake Michigan!
For dinner the first night, we at at The Beach Chicago event, so night 2 was our only night on our own to eat. Not wanting to go out in the cold again, we ate at Coq d’Or inside The Drake. While the food was amazing, this wasn’t the most kid-friendly location, with no kids menu, and not a lot of options for a picky 2 year old.We started with the soft pretzel and calamari, and for dinner, I ordered the crab cakes, while Dave opted for a a salad with the clam chowder. I highly recommend the calamari here! The Coq d’Or staff went above and beyond to welcome us! Our server made it fun for the girls, and even brought them each a cookie before we left – he joked that they were 3 years old, which they thought was hilarious!
What we did
We didn’t let the storm keep us cooped up, we found plenty of activities and places to explore (while getting out of the snow!)
The Beach Chicago
Friday night, Hilton invited us to take a break from the cold and head to the beach. Yup, you read that correctly! The Beach Chicago is an interactive art installation at Navy Pier, that features over a million plastic balls, deck chairs, and umbrellas. If you’re staying at a Hilton hotel, guests can show their key card to receive complimentary fast pass access to the event!
They have bins for you to stash shoes and other items, but you’ll definitely want your camera handy – The Beach is a photo-op gold mine! They have the cutest pool floats and beach balls for you/your kids to play on, and 3 “docks” that extend into the balls. You can head to my Chicago highlight reel on my Instagram to see more from The Beach Chicago, and learn more at Travel.Hilton.com.
A few tips for your trip to The Beach:
- Wear socks. Guests are encouraged to remove their shoes.
- If you’re being dropped off, you’ll want to be at Entrance 2 of the Aon Grand Ballroom – if you’re driving and parking, the East Garage has the closest parking!
Skydeck
Saturday morning, we woke up early and headed to Skydeck. They graciously opened their doors early for us, and gave us a private escort up to the 103rd floor. While we woke up to the beginning of the snowstorm, and we didn’t have the best visibility, it was still SO fun! Peyton had no fear, and was jumping around on The Ledge with me.
Skydeck is part of the tallest building in the Western Hemisphere! From the glass ledges (that extend 4.3 out), and 1,353 feet above the city, you get amazing views of up to 50 miles – and on a clear day, you can see into four states!
There is a parking garage right across the street from the Franklin Street entrance to Willis Tower, called Tower Parking. You’ll want to park there, and enter Willis Tower through the Skydeck revolving doors (on Franklin Street).
Shedd Aquarium
Later Saturday, we had a complimentary visit to Shedd Aquarium. I have never seen London so focused on something as she was with the big shark enclosure downstairs! She was in awe. It was the cutest thing – we had to say her name like 3 times to get her to snap out of it!
We watched the dolphins splash around and checked out fish from all over the world. Peyton was so excited to see a stingray, while London and Addy had fun with the penguins.
My favorite thing about Shedd Aquarium is how engaging they make it for kids. They have so many low tanks, so little kids/toddlers can see. They also have touching tanks, interactive games, and the coolest coral decorations – so you actually feel like you’re in a reef! I cannot recommend this experience enough for younger kids. If you want to see one of the aquatic shows, you need to reserve your spots at the kiosk the day of your visit, so keep that in mind when you arrive!
If you’re not being dropped off by a taxi or Uber, and you’re not going to pay to valet, expect to walk. David dropped the me and the girls off, and he ended up having a ten minute walk from the parking garage.
Shopping
We walked from The Drake to do some shopping at 900 North Michigan, but mostly so the girls could ride up and down the escalators. With wind gusts over 40mph, we had to get creative to let them burn off steam – and that mall is very narrow with 7 floors!
After we checked out of the hotel on Sunday, we drove up Michigan Ave, parked, and walked to The Disney Store. We ended up being first in line to walk in, and Peyton was able to “open” the store with Mickey’s magic hat. It was quite the show, and completely made her (and my!!!) morning!
While we had big plans to walk around Millennium Park to see The Bean and maybe ice skate, we opted out, based on the weather. Next time, Chicago 😉
This post is sponsored by TravelHilton.com, all content and opinions remain our own.
We absolutely love The Drake! When your girls are a little older, you’ll have to go back for Tea!! They do this whole thing with American girl dolls too!
Oh fun!!! We definitely thought about the tea room, but Lo and Addy are a little young – next time!!
This is where Frank and I stayed while in Chicago! We really liked the hotel a lot.
It’s a gorgeous hotel!! 🙂
I had no idea there were SO many family activities in Chicago! I need to try a few of these places when we fly up in the fall.
OH yes!! If the weather is still great, definitely walk Navy Pier and check out the zoo!
Ok thoughts!
1) stunning hotel! I’ve always heard great things about the Drake and these pics are just amazing!
2) for being such a high end establishment it seems like they did a great job taking care of a family with young kids!
3) the Beach is so cool!
So glad y’all had a great time!!
Ok soooo
1) I cannot believe we’ve never been to the drake before – it is STUNNING.
2) yes! Even though the restaurant wasn’t catered towards young kids, the staff went above and beyond to make out time enjoyable!
3) it was AWESOME. you should fly up!!
Thank you!!
This looked like SUCH an amazing trip. I love how kid friendly you made Chicago. It has always seemed like such an adult type city to me.
The Beach seems like such a fun idea! Props on suggesting wearing socks!
I’m so glad you guys had such an amazing time!!
Ha! Definitely packed socks once I heard we would need to remove our shoes — and I wanted to make sure I wrote about that, so people could prepare!!
thanks so much!!
I’ve been to Shedd aquarium so many times with my boys, and it never disappoints!! I love the downstairs level with the whales and dolphins! We always do that first!
I’ve been following your blog forever, and it’s reallr cool to see you doing something and going somewhere I go!
I loveeee the downstairs at Shedd, too! Have you stayed for one of the aquatic shows?!