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September 2017, we took Milana to Chicago. Dave and I had been before Milana was born, but this was her first trip here. We were hoping for some nice fall weather before their winter hits, but no such luck! It was in the 90s and humid the entire time we were there, limiting what we can do outdoors. Despite the awful heat, we still had a blast.
We split our stay between two hotels, the first being the Cambria Hotel which was in an excellent location and one we got at a steal on Hotwire. Our room was huge with king bed, office area with a desk and a living room that had a pull out couch.
Our second hotel was the Residence Inn Chicago Downtown hotel, which we used Marriott points for. If you are not a Marriott rewards member, you are missing out! They treat their award members really well and having gold status with them means we get a ton of perks! Our rooms are now ready before 10am, we get 4pm check outs, free upgrades to huge rooms and free breakfast which is worth it especially since many hotel buffets are $25 and up a person! I highly recommend getting the new Marriott Premier Plus card and start getting rooms for free! The current sign up bonus is 100k and it won’t be around forever.
THINGS TO DO
There are lots of things to do with kids in Chicago! One of our favorite things to do when visiting a new city is visiting their children’s museum. Chicago’s is located on the Navy Pier, so we headed there to escape the heat. We have been to many children’s museums all over the world and this wasn’t one of our favorites. Normally, we spend around 3 hours during a visit however after just one hour, Milana was done and I couldn’t blame her. For $14/person, I expected a lot more and it lacked a lot. The employees looked bored, were not engaging at all and the activities here weren’t very thought provoking. Milana’s favorite part was the art studio, where she made a cape for her Beanie Boo. It might be better for younger kids!
After the museum, we walked around Navy Pier a bit and Milana wanted to ride the ferris wheel so we did. It’s air conditioned inside, so it was perfect! If you’re a first timer to Chicago, you mind find this list helpful with things to do on your first trip to the city.
The next day, we headed to the Lincoln Park Zoo, which is free! Unfortunately because of the heat, most of the animals were nowhere to be seen. We walked around for a little bit and then headed to the children’s zoo to play inside. This zoo is super cute though so if you happen to get a cooler day, definitely come here and check it out!
A short walk from the zoo is the Nature Museum. We both loved this place and agreed that it was much better than the children’s museum from the previous day. Had I known about all the exhibits here, we would have skipped the children’s museum and came here instead. We spent over 2 hours here and Milana had a blast! They too have a water area for kids to play in, a room with a climbing structure for them and a ton of nature related exhibits. And coming soon, is a temporary exhibit called in your backyard which looks really cool! But the highlight of this place is their butterfly garden, where you will see lots of beautiful butterflies flying around as you walk around. And if you have a membership to any other museum that participates in the ASTC Travel Passport Program, this museum is free (among many others in the city!)
Another thing we love to do when visiting a new city is explore their playgrounds. One of the best in Chicago is Maggie Daly park, located right in downtown. The climbing structures are awesome and they have separate little areas with different things (boat, swings, splash pad, etc). Milana loved this park and had a blast playing. The biggest downside were the slides. We’ve been to other parks all over the world where they used material that doesn’t get hot from the sun. I figured since this park is so new and their summers so brutal, it would be the same. But after touching it, we quickly realized why no one was using the slides-you are sure to get 3rd degree burns if you did! So she only got to enjoy a couple of the awesome slides during our visit.
Another awesome playground was Oz Park. In this park, there were Wizard of Oz statues scattered throughout and Milana had a blast finding them. The playground here is really nice too and fully fenced in, which is perfect if you have a runner! And because of all the trees surrounding it, the playground was almost fully shaded which was great in the heat!
Of course it’s not a visit to Chicago without seeing the Bean! Milana loved seeing it and loved seeing her reflection and the reflection of the city. Come in the evening around sunset, it’s really beautiful then!
Because it was so hot, we walked to the Crown Fountain which is located right next to the bean. The first time we went, we didn’t bring a change of clothes. But she loved it so much that we came back the next day more prepared!
In the evenings once it cooled off a bit, we walked around the city exploring the different areas.
Perhaps the food Chicago is best known for is deep-dish pizza. When we arrived at our hotel around 9pm, we discovered that Ginos East was right next door, so we ordered some take out and had our first taste of Chicago pizza! Milana is not a pizza fan at all but loved this one! She ate so much, I’m not sure how such a tiny thing can fit so much in her stomach! Every day after that, we noticed the huge lines outside of this place so be sure to get here early or risk having a very long wait.
Another deep dish pizza place we tried was recommended by a lot of locals, Pequods Pizza. Now I know they have a huge following but we didn’t like it at all! Had this been our first experience, we probably wouldn’t have had a 2nd. What they call “caramelized” crust is actually burned to a crisp and black and inedible. The sauce was awful and the pizza just wasn’t good. We each ordered our own personal pies and none of us ate much of it.
Down the street from Pequods is an awesome little bakery cafe called Sweet Mandy B’s. They have lots of options, so everyone in your party is bound to find something they like! The decor inside is really cute too.
A short walk from our hotel was Eataly, which we used to love in NYC. This one is much smaller though the food options seem similar. We ate at one of the restaurants and while the food was good, we felt it was way overpriced for what you get and I would recommend finding a more local place to dine in. The kids menu was pretty cool-they pick the shape of their pizza and toppings, and it’s brought out to them looking similar to the picture. I had the pappardelle for my meal, Dave had the 5 cheese pizza and Milana chose the fish pizza which she didn’t eat because she ate most of my meal! We also got some really good in-house made mozzarella with pesto. I highly recommend this!
Downstairs, you will find all sorts of desserts. Milana saw the nutella cafe and had to have a banana/nutella crepe. I opted for some gelato.
The Revival Food Hall is another fun place to check out. There are lots of dining options here, so each member of your family can have something different. One of the best things we discovered here is the hot chocolate from the Hot Chocolate Bakery. Now most people aren’t ordering hot chocolate when it’s 90 degrees outside, but we did! We heard that it’s very similar to the one at Angelina’s in Paris (best hot chocolate in the world!) and it sure was. Not the same but the closest we have found so far. Definitely give it a try!
For lunch, Milana and I shared some pulled pork from Smoque BBQ and Dave had the famous spicy chicken from The Budlong. Our food was good, but Dave’s chicken was pretty awful! The lines for the chicken are huge but honestly the hype isn’t worth it.
If you are looking for one of the best breakfast places anywhere, head to Wild Berry Cafe. Be aware that the wait here, even on a random weekday, is over an hour. However if you go on Yelp, you can opt to skip the line. We did this while at the hotel and when we arrived, all we had to do was check in and our wait was less than 5 minutes. There were a ton of people waiting so be sure you do this or risk waiting with cranky, hungry kids!
The food here is awesome. They have so many different pancake, waffle and crepe flavors to choose from as well as the traditional breakfast items. Milana chose the cinnamon roll pancakes from the kids menu and they were amazing. I had the berry crepes, which were really good too.
On our last night, we headed to the Siena Tavern for dinner. Milana loves all kinds of cheese and was very happy to learn that they had a cheese plate on the menu! I shared the pappardelle with her for our entree and Dave had the osso buco.
For dessert, we walked 2 blocks to Firecakes for some donuts, which honestly were nothing special and quite stale! We have a place near our house that bakes in small batches and replenishes with fresh, hot donuts hourly. I wish more places did this so that they don’t sit around for hours!
Overall, we had a great trip and Milana had a blast exploring new places. The highlight was the Nature Museum, which I highly recommend visiting! And don’t forget to get some hot chocolate at the Revival Food Hall!