We love Chicago, and were so excited to head back to the Windy City after our snowy weekend in January. Chicago has endless options for things to do. We are so excited to be partnering with Hilton to talk about the Experience Chicago package, and how you can have a family-friendly weekend in Chicago.
Where We Stayed
This time, we stayed at the DoubleTree by Hilton Chicago – Magnificent Mile. First things first, the location is amazing. We were just a few short blocks away from all the dining and shopping on Michigan Ave (the Magnificent Mile). The view from our window was awesome.

The hotel had a rooftop pool, which our room looked down on. The rooftop featured a bar, lots of seating around the pool, and a foosball table and pool table. It was complete with string lights that gave it the best ambience in the evening! The hotel does provide towels, too, so that was a bonus.
The hotel has its own parking ramp, but does not offer valet. Dave did not have a problem finding a spot. I will mention it is tiny! We have a Yukon Denali, and it was a pretty tight fit to get into the spaces – if we had our Thule on top of the truck, it would not have fit. So keep that in mind!
We had adjoining rooms with the girls, our room was had a king bed, a super comfy chair, and a window seat that I basically lived on. The people-watching and city views were so good! The girls had 2 double beds, and a window seat as well. Both rooms had a mini fridge and plenty of space for the girls to play.
You can shop this outfit here.
I want to take a moment to mention the staff here! We stay at a lot of hotels, but the staff at this DoubleTree went above and beyond to make the girls feel special. Peyton befriended a porter at the hotel named Ben. He gave Peyton rides in and out of the hotel on one of the luggage trollies, and made sure to wave to the girls each time we saw him. The breakfast staff was also so friendly, and eager to help. The girls are still talking about how nice everyone here was! They certainly helped make our family-friendly weekend in Chicago a success!
What We Did
When you book a Chicago Hilton, you have the option to book with the Experience Chicago Package. This grants access (and some killer discounts) to area attractions, shows, and restaurants. We took full advantage of the Experience Chicago Package, and planned our weekend around that!
360 Chicago + TILT
With the package, you can receive a complimentary TILT ticket at 360 Chicago Observation Deck. Unfortunately, when we went, it was super foggy, so visibility wasn’t great. It was still VERY cool. You go up to the 94th floor, and stand on an observation ledge. The ledge slowly tilts you out, so you are looking down at Michigan Ave below! This is a family-friendly thrill – Peyton LOVED it.

The rest of the 94th floor features glass windows, so you can walk around and get a 360 degree view of Chicago. They also have a bar – which would be such a fun place to grab drinks and watch the sunset!
The Brookfield Zoo
We headed to the Brookfield Zoo on Saturday morning. With the Experience Chicago Package, you can score 10% off admission. The zoo is huge – we spent a solid 5 hours there, and had it not started raining, could have stayed longer!
You can shop the girls’ rain coats here.
Right now, the zoo is featuring the Brick Safari Exhibit, which is open through September 29. The exhibit features 40 life-size animals, all constructed out of LEGO Bricks! Each animal sculpture has a sign next to it, stating how many bricks were used to create it, as well as how many hours each took to construct. The exhibit also has a few interactive games for kids, like True/False questions, and a mission to find 2 lost baby penguins!
I want to note that the zoo does have a little kiosk with a few beers on tap as well as Mai Tais. We grabbed a drink before hopping on the Motor Safari Tram – a shuttle that takes you around the zoo, and shares some fun facts about the animals.
The girls loved seeing the geese and peacocks roaming around, as well as the Hamill Family Wildlife Encounters. I don’t want to call this a “petting zoo” because it was way cooler. The girls were able to walk around and interact with goats and llamas, but also got to walk around a Bennet’s Wallaby enclosure – we even got to pet one!

The zoo also features a carousel. It was so fun, and featured SO many different animals to ride on.
The Pool
We enjoyed the rooftop pool at the DoubleTree, which is accessible on the 5th floor. The girls played in the water, and had some fun with the foosball table, too! If you peek to the East, you can catch a glimpse of Lake Michigan. The pool is open daily, and was never too crowded while we were there!
Shop my swimsuit and coverup here.
The Magnificent Mile
We spent the rest of our time walking around Michigan Ave. We did some shopping, and the girls had a blast in Dylan’s Candy Store and the Disney Store. I love the view from the DuSable Bridge, so we made sure to walk that way, too.
Shop our outfits here.
You can shop my outfit here.
Where We Ate
Gino’s East
Another part of the Experience Chicago Package is saving $10 on your meal at Gino’s East, which was a short 7 minute walk from the hotel. You haven’t lived until you’ve had Gino’s Pizza. We tried their new(ish) thin crust and were blown away by how good it was!

If you’ve been to Gino’s you know all about the writing on the wall! The girls were SO excited that they got to write their names on the wall after our meal!
The Hotel
We had daily breakfast at the hotel. We did the buffet which had a bunch of options like eggs, sausage, bacon, potatoes, cereal, yogurt/parfaits, and a lot of bakery options. Peyton said they were the best scrambled eggs ever, and went back for seconds each day. I loved the selection of fresh fruits, too. We got down fairly early each day for breakfast (around 8), and never had a wait.
Grand Lux Cafe
We had dinner Saturday night at Grand Lux Cafe. It was our first time dining here, and I cannot recommend it enough. It was fairly busy, but we were able to be sat right away at 5:30, when we left, there was a big wait, though!
I ordered the ceviche and the ahi tacos – both were amazing. David had a burger, and gave it two thumbs up. We loved all the options on the kids menu, and the staff was so friendly.
We had the best weekend, and are always so excited to discover new fun things to do in the city! You can head here to see our cold weather Family-Friendly Weekend in Chicago Travel Guide.
Thank you to Hilton for sponsoring this post. All opinions and content remain our own.
My hometown! That is one of our favorite zoos!!
Oh!! Fun! This was our first visit to this zoo – we’ve done Lincoln Park, but this one was way more fun for the girls!
How fun! I want to go here!
It was a blast!!