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Writer's pictureJamie Webb

Spring Break in Chicago with 4 Kids in 4 days

Last year, we decided to visit Chicago for spring break. Call us crazy for flying with four kids during a pandemic, but I am all about balancing being safe (masks and hand sanitizing when needed) and making memories with the kids. It's important to us that we model and teach the kids to seek happiness in any situation. Plus, Victor and I have figured out how to make traveling doable with kids and babies/toddlers--but that will be another blog post.


Here is a run down of our 4 day trip in Chicago. (BTW, because we are a big family, more days = more money for a hotel and car rental-- so we tend to cram a lot of experiences into our short trips!


Day 1


By the time we arrived and settled into our hotel in Chicago, it was the afternoon. We stayed at the Cambria Hotel Chicago Loop in the Theatre District in Downtown Chicago. We loved it. It was recently renovated, super cute, and very spacious for our family of 6. Our 8, 6 and 4 year old slept on one bed and the baby slept in our travel pack-in-play. The room had a dining table, fridge and sink, which is great when you have kids. Plus, the hotel was walking distance to the Chicago Theatre, Millenium Park, and Maggie-Daley Park--all of which we walked to on day one.



In a nutshell: our first day in Chicago



The walk from our hotel to Millenium Park was about 10 minutes and was a great opportunity to take in the beautiful cityscape. There, we of course took a picture at the Cloud Gate ( or "The Bean"). That is also a great time to visit Crown Fountain, which we regrettably did not get to do because it was closed at that time due to the pandemic.


We then walked across the amazing stainless steel BP Bridge on our way to Maggie-Daley Park. The kids loved running around there, and we even came back on day 2 for the scooter rink. They even have a playground there--which we did not get to take the kids to because it was closed due to the pandemic, but the kids still had a lot of fun.




After some sight seeing, we walked to The Dearborn which was literally across the street from our hotel. The beauty of it: yes great food, but also great drinks of the alcoholic variety that Victor and I could actually enjoy because we did not have to drive. #priorities

yummy ceviche



After dinner, we walked to Target which was less than 10 minutes away because the Lord knows that if it were a longer walk, we would have driven lol. Whenever we travel, we like to go to Target on the first day to buy a case of water, toiletries, milk for the baby, and easy food/snacks to pack for the kids. The walk back was another great opportunity to take in the cityscape at night. And just like that, day 1 was in the books!




Day 2


So days 2 and 3 we opted for pure walking and public transportation to get around as opposed to our rental, and I have to say it’s completely doable with 4 kids. We purely relied on Maps on our phones to help us figure out which buses or trains to take, and it was actually kinda fun and exciting for us and the kids considering we are total Californians that rely on our cars to get anywhere. You can get the Ventra app to purchase a Ventra card. I’d recommend getting 1-or 3-day passes.



Our first stop was walking to a Starbucks on the way to our bus stop because again, #priorities. We then took a few buses to the Field Museum, which only took 30-40 minutes. It’s right by Soldier Field and Shedd Aquarium. If we had extra time and money, we would’ve gone to Shedd Aquarium but given the option to just choose one, we chose the Field Museum because we live in San Diego where there’s plenty of opportunity to see marine life between Birch Aquarium, Sea World, tide pools, or whale watching.

We make it a point to try to go to places when they first open to avoid crowds, so we went right when it opened and I’m glad we did. When you have kids, you already feel like you’re walking a tight rope when you go places, so crowds and lines is not the way to go. We stayed for about 3 hours and enjoyed seeing the dinosaur, animal and mummy exhibits. They have plenty of seating areas/tables if you need to squeeze in snack time (this is where our Target trip came in clutch because we were ready with water and snacks in our backpack).






When you’re done at the Field Museum, hit up Kim and Carlo’s Hot Dog stand for a Chicago Dog. So. Freakin. Yummy.



Our next stop was back to Millenium Park again where we walked and enjoyed the city sights until we hit our intended destination: Maggie-Daley Park. We wanted to take the kids there so they could do the scooter rink. They had a lot of fun, and because it was Easter weekend, they also got free loot bags with Easter eggs, candy, and crafts.



From there, we walked back to the hotel and took a breather before dinner. Dining was challenging at that time because with COVID, there were restrictions with indoor capacities at restaurants. Plus, I am such a foodie and refuse to just go to any restaurant—the food has to be good. But the caveat to that was there was an hour and a half wait to where we wanted to eat: Ramen-San at North River. Luckily, I did my research on the area, and we got creative with our time. We flipped dessert and dinner. Unconventional I know, but it’s vacation. We walked over to JoJo’s Shake Bar- River North where there was no wait because everyone else was eating dinner. It has a Candyland feel to it with great 90s-early 2000s music playing. The desserts are fun and we got some really cute pics out of it. It was almost our oldest kid’s birthday, so they even played 50 Cent’s “In Da Club” when they brought out his dessert complete with candles.



By the time we were done, our table was ready at Ramen-San, which was super yummy. And that was day 2!



Day 3


As always, we start our day with coffee and our first stop was this super cute hidden alley coffee shop called Hero Cafe.

We then bussed it to the 360 Chicago Observation Deck. It was such a beautiful day to see a literal 360 view of Chicago.



From there, we walked around, did some sightseeing and shopping before taking the bus to see Wrigley Field. Victor and I love baseball, and although we didn’t have tickets to see the game, it was opening week and there was a game in progress so it was cool just experiencing the vibe of it all. We had lunch in the area and the took the train back into the city, which honestly—-public transportation for these kids is exciting in itself when you’re from California.


Outside of the pandemic, this would have been a good opportunity to check out Navy Pier, but it was closed when we went. Instead, we walked over to a park overlooking the lake and let the kids play while we enjoyed the view.


Day 4


This was our last half day in Chicago before driving to Iowa to visit Victor’s family. We went to the Museum of Science and Industry, which was super fun, interactive and educational. We spent 3 hours there and they had a great cafe where we had lunch before our drive to Iowa.



It was definitely challenging navigating a vacation with all of the COVID restrictions and closures at the time, but we still made the most of our time and had a lot of fun.


Check out our instagram reel of our trip to Chicago.






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