My husband is from the Midwest and we try to make regular visits to visit family. Sometimes these trips serve as our main family vacation so I try to build travel into our family trips as much as possible. In the summer of 2023, we decided to add a two-day Chicago extension to our regular Midwest family trip.

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It all started with the goal of going to a Cubs game at Wrigley Field. This has been a bucket list item for my mom for a long time. We had plans to go in 2020 but it was canceled due to Covid, so we revisited the idea of going to Chicago a few years later for her 70th birthday. She and my dad decided to meet my family in the city for a brief getaway.

I spent a lot of time researching and travel planning so I thought I’d share my itinerary. Chicago is a huge city with tons to do, so I know we barely covered any ground. But, maybe this itinerary will serve as a starting point for some plans you might be cooking up if you decide to visit the Windy City.

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Summary

  • When: May 2023
  • Time: I’m saying two days here – two full half days, one full day, and two overnight stays for roughly 48 hours total
  • Kids ages: 4 years, 2 years, and 3 months
  • Transportation: We had our truck for my family. We went to spend time with family in the Midwest and spent roughly 48 hours in Chicago on our way home from the Midwest. My parents flew in and took public transportation to meet up with us.
  • Lodging: We opted for an Airbnb instead of two hotel rooms so we could all stay together, and for walkability purposes that I’ll get into.

Planning the Trip

Let me walk you through how I planned this trip. The main reason for the trip was a Chicago Cubs game. I purchased tickets to the game first. With a new baby, I didn’t plan a very ambitious itinerary. We for sure wanted to do the game, and then I thought maybe we could just walk around a check a few things out.

I started researching things to do and mapped out some activities within walking distance, getting a sense of the area I wanted to stay. Below is a map for reference. Things in pink are places we went to and things in brown were places on my radar that we didn’t make it to. I’m sure there’s a lot more we could have done in this area.

Lodging

Next, it came time to book lodging. We ended up splurging a bit and stayed in a skyscraper Airbnb which turned out to be an incredible experience that I’ll never forget.

I’ll admit, I was intimidated taking on a huge city with three kids including a new baby. I didn’t anticipate covering a lot of ground, so I wanted to be able to walk to a few desired activities. So I splurged for location and walkability.

Although the Airbnb was more than I thought we would spend (our stay was not sponsored), it was pretty comparable to the cost if we had gone with two hotel rooms nearby. I appreciated having my folks stay with us instead of in separate hotel rooms. We picked up some groceries on the way in, mostly for breakfasts and snacks, but we did spot a market nearby walking around if we needed something.

I’ll never forget the insane views, the beauty of seeing the city lights in the dark, watching window washers, admiring the sunrise over Lake Michigan, searching for boats and kayakers on the Chicago River, and so much more.

Both the kids and adults loved this rental, a great choice for families. Truly unforgettable.

So let’s get into the itinerary.

Day 1

On day one, we had a check-in time around 3:00. We arrived in Chicago mid-morning and needed to kill some time before we could check in. We wanted to visit a museum or something similar and decided to go with the Museum of Science and Industry.

There was a parking garage below the museum that we paid to park in. I also noticed some nice green spaces and playgrounds within walking distance. We were only there a few hours but could have spent a lot more time there. There were so many neat exhibits plus an entire children’s play area. We were happy with this choice.

With such a large city, there were several other places we could have gone. Here are some other places I was eyeing up to fill that time including:

After the museum, we headed to the Airbnb to check in and settle in a bit. It was a little stressful finding it, and our F-150 barely fit in the parking garage, but it did! After we parked, we never used our vehicle until our departure utilizing walking and public transportation for the duration of our stay.

We decided to venture out on foot after we unpacked. Just outside the Airbnb we took our double stroller and child carrier and went for a walk heading for Millenium Park.

But, we stumbled upon a neat playground at Maggie Daley Park right next to Millenium Park and ended up spending the entire evening there.

The park had multiple playgrounds and other things we didn’t even get to like mini golf.

As it was getting dark, we decided to pick up some takeout for dinner and eat it back in the Airbnb. There were lots of walkable eateries to choose from. We were happy with our choice of Gordy’s Tiny Taco Bar. Then, we called it a night.

Day 2

On day two, we waited for my parents to arrive. Their flight arrived in the morning and they took public transportation toward our lodging. They were pretty intimidated by the thought of taking public transportation, but I walked them through it and they did it, admitting it was smoother than they anticipated. From the airport, they took the Blue Line to a stop fairly close to our Airbnb where my husband went out to meet them to guide them in.

Tip for using public transportation: I wasn’t always savvy with navigating public transportation, but with a simple tip from Google Maps, I now feel like a pro. Simply type in your locations and select the public transportation icons to get a list of your public transportation options.

We decided to book an afternoon Chicago Architecture Cruise and had some time to kill. So we ventured out on foot with our double stroller. First, we walked to Millennium Park, stopping for an obligatory photo-op at The Bean.

Then, we walked through Millenium Park and took an awesome walking path that connects back to Maggie Daley Park where my kids wanted to show my parents the playground and play there for a bit.

Next, we headed for the Chicago Riverwalk. We had trouble getting our stroller from W Wacker Dr down to the level of the river and carried it downstairs. But, I think on the way back up, we eventually did find a ramp near N Orleans St.

The Riverwalk was loaded with eateries and was a beautiful place to walk around. While we waited to board our boat for the architecture cruise, we enjoyed a Chicago-style hot dog and cider at The Northman Beer & Cider Garden nearby.

We took our seats on the top deck of the boat for the architecture tour. It was really interesting, but my kids didn’t attend too long. Luckily, the kids could walk around the boat and we ended up having a dance party on the bottom floor with snacks while my parents listened to the guide the entire time.

I don’t think it’s an activity geared toward little kids, but my kids still enjoyed a boat ride. I will say with my little kids, I’m glad it wasn’t longer than 90 minutes.

After the boat cruise, we headed back toward the Airbnb to regroup for the Cubs game. This was the most stressful, but the most exciting time. The kids were already tired and the baby’s nap schedule was off. But, we got our Cubs gear on, had a snack, and powered through.

There was added stress because we took public transportation and I hadn’t done it (but since my parents did when their flight arrived, they were feeling confident). We figured it out together and the CTA workers were very helpful in guiding us where we needed to go.

Additionally, we didn’t take our stroller (just took a child carrier for the baby). The train kept getting more and more crowded as we approached Wrigley Field. I don’t know if taking a stroller would have even been possible. Thankfully, my parents were able to help carry the kids when needed since we didn’t have a stroller.

The beauty of taking the Red Line was that it dropped us right at Wrigley Field. We went directly into the game, but Wrigleyville looked like a blast. Some places I eyed up but didn’t make it to included Gallagher Way and Sluggers.

After we settled into our seats for the game, knowing so little about Wrigley Field, I started to understand why this was on my mom’s bucket list.

I was juggling the kids, but here are a few things I noticed a few things that made Wrigley Field feel like a snapshot of American history. I loved that the scoreboard wasn’t digital and that people changed the numbers.

It was so neat how the ballpark is situated right in a neighborhood where people were watching the game from surrounding rooftops with no parking lot to be found. I also laughed when I saw several seats located right behind a column, relieved I didn’t happen to buy one of those tickets.

There’s also a first timer’s booth that all the friendly ushers reminded us about. Plus, the food options were so basic like a big concession stand, which I liked, just the standard options like hot dogs, nachos, etc. It just felt like a nostalgic American ballpark.

We didn’t make it through the whole game and wanted to start heading back before it got dark. We loved getting our picture at the red marquee on the way out. The picture depicts some tired kids and some adults smiling through some stress, but I loved our adventure to Wrigley Field.

It was a long exhausting adventours day. I think we walked 8-9 miles.

Day 3

On day three, my family left my folks who stayed one more night on their own. We spent the morning together and had lunch with them before departing. We decided to walk to Navy Pier via a nice walking/bike trail.

We wanted to visit the Children’s Museum, but it was closed.

So we just walked around the pier and had lunch at Giordano’s to grab an obligatory deep-dish pizza.

Navy Pier felt a little touristy to me, but we still had a good time. It was more windy the further out we ventured onto the pier, but the area offered a nice view looking back at the city skyline. There was a Ferris wheel and boat tours you can look into among other activities.

I thought my parents would go to a museum or something for the remainder of their time, but they shared that they simply enjoyed relaxing, grabbing a bite, and walking around. The following morning they took the Blue Line back to the airport and flew home.

One thing I want to make note of is that we visited Chicago at a time when it seemed to be making the news in negative ways constantly. I just want to say I don’t doubt there are issues there, as many places have problems. But, I just want to share that we had absolutely no issues. In our experience, the city was clean and lovely, and frankly one of our best city experiences ever.

I parted with a smile on my face while humming Frank Sinatra’s “My Kind of Town” for sure.

That’s how we spent about 48 hours in Chicago with kids. I hope you found this helpful. If you go to Chicago, be sure to tag me on Instagram (@adventureswkelly) so I can see your adventures. If you have more suggestions to add to this post, feel free to leave a comment. Happy travels!

If you found this helpful, be sure to check some of my other travel itineraries: