Long Weekend Trip to Chicago

We recently traveled to Chicago for a long summer weekend and it was a BLAST. Emilia and I traveled together on Thursday and then Josh joined us on Friday. Because it was a shorter trip and Serena isn’t really enjoying air travel at the moment, we decided to do a big sis trip this time around!

When traveling to Chicago, my first recommendation is to always travel to Midway instead of O’Hare. It is less busy, easier to navigate and the drive isn’t terrible from there to the city. We decided to rent a car because we were going to be around a lot of the city and with Emilia being in a car seat, it is easier for us to bring our own travel car seat and to rent a car.

Maggie Daley Park

We have family in Chicago so we stayed in Lakeview the first night we were there and had a chance to explore that area there. Upon arriving, I discovered something unique about the playgrounds in Chicago. 1. There is basically a playground to enjoy in the city every few blocks. 2. A lot of playgrounds are connected to the local schools! You just simply use them when school is not in session. This is definitely not a thing in Atlanta so I thought it was so neat.

The first day we were in Chicago, we walked down a famous street called Southport where you can find shopping and delicious restaurants. We ate at Crosby’s Kitchen for lunch, which is very kid friendly. After, we went to a local park called Juniper Park (although there is actually a park even closer to Crosby’s!) Juniper Park had a large sand box and so much water play! You could find water tables, a splash pad and water play by the sand too. What a fun place to play!

Our second day we went back to Southport for a walk with friends and then enjoyed bagels from Steingold’s- so delicious! Also, the Starbucks there is very friendly and even gave Emilia a sticker!

After bagels, we took a trip to Hyde Park area (benefit of renting a car because it’s not that close) and went to the Museum of Science and Industry. If you choose one museum to go to when in Chicago, please make it this one. I kid you not, this is the most incredible museum I have ever been to.

We saw baby chicks hatch from their eggs for the first time!

We spent FOUR hours there. There are several floors and so many different topics to explore. From going inside a real airplane, train or submarine to learning about storms or the inside of the human body. We both learned so much!

Idea Factory: get timed tickets for this children’s section when you first arrive

After spending the afternoon at the museum, we checked into our hotel. We stayed at the Park Hyatt on Michigan Ave. It was a great location and wonderful hotel to stay at. It is kid friendly and the food was really good!

It was such a gorgeous view from breakfast!

It is also dangerously across the street from Water Tower Place which is a popular shopping destination on Michigan Avenue…and houses the multi-level American Girl store. That store is quite the experience. If your child enjoys dolls, this is a very unique place to visit.

This was in the itty bitty baby area

I’ve also stayed at the Westin across the street which is a great option too. I love this location because it’s close to the famous shopping on the Magnificent Mile and Oak Street Beach/the lake!

After we checked in and did some shopping, we met our family in Lincoln Park for a dinner at Homeslice and it was so good! I had the kale and cashew salad and I am still thinking about it. Also- if you have young kids, they have a happy hour half price menu. So if you eat early like us and get there before 6, you get a little discount :)

After dinner, we grabbed dessert at Sweet Mandy B’s down the street. This is a famous dessert spot in the Chicago area and they are known for their delicious cupcakes and cookies.

And then of course stopped by a playground on the way home. This was again at a school and it even had chickens and ducks there!

The next day, we found a playground near our hotel called Seneca Park. It had two different areas for young kids and older kids. We went to Wildberry for brunch (very large breakfast spot) and it was the perfect park to play in while we waited for our table!

The younger play area at Seneca Park

Older kid section at Seneca Park

The brunch spot has every type of pancake possible so if your child enjoys the sweet pancake mix-ins, check it out!

We ordered the oreo pancakes :)

After brunch, Josh and I attempted to do some adult errands with Emilia…but it got pretty crowded and was hard to do. We first tried to go to the Hoka store (best sneakers!) and then get coffee after. There is a Starbucks Reserve on Michigan Ave (which we didn’t make it to) but apparently, it is incredible. I think it has four levels and each level is a different experience- there is coffee, alcohol and food depending on the floor. This is definitely on our list for the next visit!

We met our family at the Lincoln Park Zoo after our errands. If you didn’t know, this zoo has free admission! It’s a really nice area to walk around and to enjoy the day in Chicago. Nearby there is also the Lincoln Park Conservatory which I’ve been to before and is really nice. And then also the Nature Museum. I haven’t had a chance to go there, but it looks awesome for kids!

This is in an indoor/outdoor play area by the farm at the zoo

However when it comes to parking in this area, prepare for it to be a bit tricky because it gets busy.

That afternoon, I took some Mommy time and went to AIRE. AIRE is an ancient bath house - basically an oasis to escape the hustle and bustle. There are different temperature baths, a steam room, opportunities for face masks/scrub and spa treatments. It is very quiet down there and you need to wear a bathing suit since everyone is using the same baths. Very relaxing and rejuvenating!

That night Josh and I went with our cousins to see Charlie Puth at Ravinia. Ravinia is an awesome concert venue located in the Chicago suburbs. They have a pavillion, but it is mostly lawn seating where you can bring/rent your own table and chairs and bring your own food too! It was such a fun way to end our weekend in the windy city.

The next morning, Emilia was very sad to say goodbye to Chicago and so were we. If you plan to travel to Chicago, I always recommend the summertime, but it really has so much to offer and you’ll love it no matter what!

We love Hyatts for many reasons but one of them is they often give you a themed stuffed animal that goes along with their hotel!