Amazing Day Trip to Chicago with Girl Scouts


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Amazing Day Trip to Chicago with Girl Scouts

Amazing Day Trip to Chicago with Girl Scouts

Chicago is one of our favorite Midwest cities to visit. We love the museums, the shopping, the culture. The looks of amazement on my kids’ faces when they see the buildings and the sheer number of people is so funny. It’s a great big world out there, and while we choose to live a very rural life, we also want our kids exposed to the diversity that is found so readily in the third most populated city in the U.S. At 3 1/2 hours away, Chicago is just close enough for a day trip (although it makes for a long day), and we make it out to Chicago at least a few times a year.

I’ve been the leader for my daughter’s junior Girl Scout trip for the last two years. At her age, many girls have left the Girl Scouts for other endeavors and our troop is quite small. I was lucky enough to have amazing experiences as a Girl Scout when I was a kid in Germany as a member of a U.S. Troop on Foreign Soil and wanted to give my little troop the experience of a life time too. Unfortunately, we couldn’t all hop on a tour bus and head to Amsterdam like I did when I was a Girl Scout, but I knew I could figure out something memorable for us to do. So this summer, I took my 4 Girl Scout Juniors and two moms on Amtrak to Chicago. We a blast walking around the city touring iconic Chicago destinations. I only wish we could have stayed longer!


Amazing Day Trip to Chicago with Girl Scouts - Galesburg, IL Amtrak Station from

Our amazing day trip to Chicago with my Girl Scouts began at 5:30 am.  We had to get up early to get to the Amtrak Station in Galesburg, Illinois for our 7:38 am train on the Chicago Zephyr. Galesburg is a 75 minute drive from our home and we wanted to make sure we arrived in plenty of time so we wouldn’t miss our train. It was a very rainy morning and I watched the radar closely, hopeful that the rain would take all day to reach Chicago so we could walk in dry weather! Luckily for us, the rain did stay away while we were in the city. According to the radar, it arrived after 10 pm and we were long gone by then. We had great luck with the weather – not too hot, not too cold. Not too humid. The only bummer was the sky was overcast and a little grey and my pictures didn’t turn out all that great.

Awesome Day Trip to Chicago with Girl Scouts getting on Amtrak from

Amtrak was such a relaxing way to travel. No traffic or tolls to deal with, bathrooms on demand, snack car, wifi, and outlets for charging! Talk about traveling in style. We all loved it – especially my Girl Scout Juniors. Not one of us had ever traveled via Amtrak and I’m confident they won’t ever forget this trip. The girls thought the food car was amazing and enjoyed walking as the train jostled around corners and down the track. I had such a great experience on Amtrak that my husband and I are looking into an Amtrak vacation with our family one of these days.

Visiting Iconic Chicago Sites on Foot

Amazing Day Trip to Chicago with Girl Scouts - Union Station from

Union Station

Amtrak deposited us at Chicago’s Union Station – a pretty amazing building. My Girl Scouts were enthralled with the huge building and I was pleased with its central location in Downtown Chicago on the west side of the Chicago River between West Adams Street and West Jackson Boulevard. Chicago’s Union Station was built in 1925 and is the third busiest rail terminal in the U.S. {after Grand Central Station and Penn Station – both in New York}. I was surprised to learn that Union Station handles 120,000 passengers on an average day – it did not seem that busy when we were there.

Awesome Day Trip to Chicago with Girl Scouts-junior girl scouts {from} After we exited our Amtrak train and made our way out of the Union Station building, it was a really short walk, not even two blocks, over to the Willis Tower to go up the Sky Deck. The Willis Tower {which a lot of people still refer to as the Sears Tower} is the second tallest building in the US and the 12th tallest building in the world.

Awesome Day Trip to Chicago with Girl Scouts Sky Deck at Willis Tower from

Most of my girls, and me included, were a little apprehensive about heading out on the Sky Deck – see-through observation boxes built outside the Willis Tower. From the observation boxes we could see an amazing view of Chicago – 4 states are visible from that height. All but one of us did eventually make it out on the Sky Deck, but I think only one girl really enjoyed the process. You’ll have to head over to Instagram to see the picture of my clutching at nothing in terror out on the Sky Deck! It’s hard to believe I used to sky dive when I was in my 20s, isn’t it?!

We had a great time on the Sky Deck, though. The girls especially enjoyed the gift shops, and several of them spent most of their money before we even left our first official stop. In all, we spent about an hour and half at the Sky Deck from start to finish. We were there on a Wednesday morning and the ticket line was very short. I had not bought tickets ahead of time, but that is something to consider if you head there on a busier day.

Millennium Park

Awesome Day Trip to Chicago with Girl Scouts Millennium Park from

After we finished at the Sky Deck, we took to the streets and headed to Millennium Park. It was a little after noon when we finished at the Sky Deck and the girls wanted to eat. Unfortunately, we couldn’t agree on food. I tried to steer the girls to something different, you know Chicago style pizza, or gyros,  or anything other than McDonald’s or Subway, which was what most of the girls wanted. It was an eight block walk down to Millennium Park from Willis Tower and we finally agreed on pizza right before we got to the park, so we took it to the park and had a little picnic.

Millennium Park - The Bean Amazing Day Trip to Chicago with Girl Scouts {from}

If you’ve never been to Millennium Park, you should definitely add it to your must visit list! Home to the famous Bean, Lurie Gardens, Crown Fountain, impressive outdoor art displays, and the Jay Pritzer Pavillion, it is a wonderful and free place to visit in Chicago. Millennium Park is located in the Chicago Loop and was within easy walking distance of Union Station. We did get a few grumbles from the girls as we walked the eight blocks, but I think that’s a totally doable distance and we were able to visit stores and do some fun people watching on the way.

Awesome Day Trip to Chicago with Girl Scouts-at the Bean from

We visit Millennium Park almost every single time we are in the downtown Chicago area and never get tired of it. Looking for ourselves in the reflective bean, and trying different poses, was a blast!

Public Transportation

Awesome Day Trip to Chicago with Girl Scouts-public transportation from {SimplifyLiveLove}

After Millenium Park, the girls were tired and started to grumble. They didn’t want to walk back to Union Station so we decided to try out public transportation to see if we could shorten our walk back. This decision turned out to be a really great experience for the girls. We had to ask people where to go, read maps, and really think about where we were and where we wanted to end up. We started on the subway and then had to transfer to the L. We saw a lot of homeless people and listened to a few really great subway musicians. When I asked the girls afterward about the trip, a couple said their favorite part had been navigating the public transportation system! At $2 per girl, that subway and L rides were pretty cheap entertainment.

We got back to Union Station around 4 pm and didn’t need to catch our train until 5 pm, so we had a little downtime at the end. We enjoyed a ice cream and found a dog park to sit in for a while. The girls were very interested in talking to people about their dogs and reflecting on the differences between city and country life. They were especially sympathetic toward the homeless people and we gave away all of our change. At one point, they stopped to read someone’s sign and a complete stranger yelled at them to go away and stop reading. “We don’t read THEIR signs,” she said. I was flabbergasted and proud of my girls for their empathy and desire to help. At what point in our lives do we get so callus? We can learn a lot by watching the way kids react to life.

Awesome Day Trip to Chicago with Girl Scouts- headed home on Amtrak {from}

At the end of the day, we caught our Amtrak train back to Galesburg. The girls were ready to charge their devices and walk back and forth to the food car. We stopped at a grocery store near Union Station and bought sandwiches and fruit for the ride home. The train ended up being more crowded on the way home than it had been in the morning and everyone was pretty quiet. We got home finally a little after 10 pm.

In all, taking the train to Chicago was a really great idea. The girls learned a lot and had a great time. I highly recommend a trip like this for your family or a group of kids you might work with. It was truly an amazing day trip to Chicago than none of us will soon forget.

Have you been to Chicago or taken a trip like this with a group of kids? What was your favorite part?

About Michelle Marine

Michelle Marine is the author of How to Raise Chickens for Meat, a long-time green-living enthusiast, and rural Iowa mom of four. She empowers families to grow and eat seasonal, local foods; to reduce their ecological footprint; and to come together through impactful travel.

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  1. It looks like everyone had a great time. I’ve never been to Chicago, but I have ridden on Amtrak. It’s a great experience and I highly recommend it to anyone who hasn’t done it before. The food cart is certainly an experience.

  2. This was a great article to read. What a lovely day you had! I live in Australia, so our cities are much smaller than yours, but we could do the same thing here, must add to the to do list!

  3. That looks like a fun trip. I think I need to put Chicago on my bucket list. BUT I’m not sure if I want to try the Sky Deck. I have vertigo. Haha!

  4. I love Chicago! Looks like you had big fun! I was a junior leader when we were stationed in Germany when my daughter was younger…we took our troop to Switzerland on a train. This brings back such memories. I miss Girl Scouts!

  5. This is so cool. I was a Girl Scout throughout my life and then went on to lead my daughter’s troop throughout hers. It truly is an amazing way to impact our girls lives. Thank you for doing this. The girls look like they had an awesome trip. I haven’t tried the “clear box” in chicago yet but I’d like to.

  6. It looks like this was such a fun trip. I love the photos–you really captured the energy of your experience. There’s no way I could go out on that sky deck. Brave girl!