Our Trip to Chicago

This past weekend, Mike and I took Liam on a special trip to Chicago. For those that don’t know, we both grew up in the Western suburbs, about an hour outside of the city. After college, I moved into the city to start my career and fulfill a dream I’d had of living in the city! I ended up spending 4 years living in 3 different neighborhoods in the city. Mike lived in the city for about 3 years and then we moved to Virginia about 3 weeks after getting married in 2017! I have some very fond memories of that time in my life and am so thankful to have taken the leap to fulfill that dream of mine.

The summer, specifically late summer, is truly the best time to be in Chicago. The weather is beautiful! I’ve been missing the energy of the city and just being “home” for awhile now, so it came up that maybe we could take Liam on a quick trip to show him some of our favorite things. My parents were game to watch the twins, so we booked a long weekend stay!

I’m certainly biased because it’s where I’m from, but I truly believe Chicago is one of the best cities out there. It has so much to offer! I love that it’s situated right on Lake Michigan, too. It was very manageable (& fun!) to explore with Liam, who is approaching 3.5 years old. I think he was at the perfect age for it because he didn’t require a bunch of extravagant plans, but also loved the special things that we did do!

What we did in Chicago with Liam:

WHERE WE STAYED

This was my first time staying in a hotel in Chicago! We stayed at the Intercontinental on the Magnificent Mile. They happened to have a promo running for a free night with a 3-night stay during our time, so it worked our perfectly. It was in a fantastic location and was very nice! There’s a Starbucks in the lobby, along with Michael Jordan’s Steakhouse. The room was plenty big enough and we had a stunning view of the city and the lake. I would absolutely stay again!

ACTIVITIES

Shedd Aquarium

We did this the first day we got there because we didn’t have enough time for the other activity we planned. I always loved going to the Shedd as a kid, so I figured it was worth taking Liam to! He fell asleep on our way there and slept for about half of our time in the aquarium, but was into seeing some of the animals and fish when he woke up. It was probably more enjoyable for us than for him!

Lincoln Park Zoo

To be honest, Liam didn’t really care about the zoo at all except for the mini train ride he got to do while we were leaving. Mike and I used to regularly walk to and through the zoo on a weekend afternoon, so it was fun to be back and walk it again. The best part is that it’s FREE! And it’s a great zoo!

Museum of Science and Industry

Taking Liam here was a big draw to making this trip happen. He loves trains and this museum has a huge model railroad that is amazing. I remember being fascinated by it as a kid and I felt the same way seeing it again as an adult. They also had some old train cars, a Pioneer Zephyr, airplanes, and a lot more to explore. He said this museum was his favorite part of the trip! 10/10 recommend going to it if you ever find yourself in the city!

Maggie Daley Park

This is a huge park with a bunch of different smaller play areas for kids. It was a great free option to let Liam burn some energy!

Walking along the Riverwalk

We stayed right down in the heart of all the action, just 2 blocks from the Riverwalk. They’ve done a ton of improvements to the Riverwalk since we lived there, so it was cool to walk along it and see what they’ve done. It’s fun to watch all the different boats come through.

Starbucks Reserve Roastery

We popped in here one evening to see what all the fuss was about! It’s a very cool store with plenty of delicious looking pastries and coffees. We didn’t get anything because it was after 6pm, but it’s worth popping in if you’re nearby.

Just Walking Around

We did a lot of walking to and from activities. That’s one of my favorite things about the city – just walking around and feeling all the energy buzzing around you. It helped that the weather was flawless. If you stay in a busy area, it can be a very walkable city!

RESTAURANTS

Lou Malnati’s

The best pizza option in the city, if you ask us! We had it for dinner one night and then did a pick-up order for lunch to eat in our hotel one day. It is so good!

Portillo’s

Another must! I dream about this food and we always make a point to stop in when we’re back in IL/WI!

Egg Harbor

A favorite breakfast place that had a location in our town growing up! Their skillets are so good!

Potbelly

We used to eat Potbelly a lot when we lived back in IL, so we knew we had to get a sandwich!

Stan’s Donuts

We popped into one of the many locations on our walk to the park to get a special treat and it did not disappoint!

Ghirardelli Ice Cream & Chocolate Shop

This was just across the street from our hotel, so we popped in one afternoon to get some ice cream.

PUBLIC TRANSPORTATION

Our flight landed at around 9am, so we had almost a full day to spend! We knew we wanted to ride the L from Midway into the city, so we made our way to the L station at the airport. Having spent 4 years utilizing the public transportation system heavily, we were both very comfortable with how it all worked and how to get around. It is pretty simple to navigate once you get your bearings. Google Maps also has the option to give you directions using public transport, so that would be a great way to know exactly where to go. The best part is that a ride on the L is just $2.50, versus the $50+ tab we would’ve gotten from an Uber. We rode the L as often as we could since Liam loved going on it so much!

We were going to ride the bus for one of our activities, but then the bus we were waiting on got re-routed due to an event, so we changed gears. I used to utilize the bus a lot when living in Chicago, so it’s another good and easy way to get around!

There are, of course, plenty of ride-share options, too!

Overall, we had such a great time and really enjoyed being back for a few days! I would love to go back as a family of 5 when the babies are closer to Liam’s current age!