We surprised our 10 year old with birthday trip to Chicago, Illinois filled with exciting adventures, amazing food, and sightseeing over 3 jam-packed days.
How to Spend 3 Days in Chicago
Not long before our oldest turned 10, I mentioned to my husband that I thought it’d be fun to take her on a solo trip to celebrate hitting double-digits. Nothing crazy, just a good 2-3 days away, just the three of us. We’d never done anything like that with any of our kids so it seemed like the perfect opportunity.
I wanted to visit someplace “new” – a city she’d never been to and one that Justin and I could still enjoy while entertaining a ten-year old. We decided to book flights to cut down on the amount of travel time since we were only planning on being gone for two nights. Our kids have also never flown before so having this be her first flight was also special.
Southwest just happened to be running one of their sales so after a quick price check, we booked cheap tickets to Chicago!
My parents graciously agreed to watch our other two – and helped us keep it a surprise until the morning of our trip!
Day 1 – Travel & Sightseeing
We started the morning at home, packing lunches and getting everyone ready for school. When it was time to load up, we finally told Gracyn that she wasn’t actually going to school – we were dropping the other kids off and then heading to the airport! She was shocked but definitely excited.
The nonstop flight from Kansas City to Chicago is barely an hour which mean we were scheduled to land by 11 am that morning – plenty of time to spend the day sightseeing and familiarizing ourselves with the city.
Even though our trip was scheduled for January, we always planned to rely on walking and using public transportation; the weekend weather didn’t look great – but it didn’t look terrible, either. It was drizzly and cool, but not snowing so getting around safely without having to rent a car was a win.
Before our trip I tried getting an idea of what trains we’d need and when but found the maps and routes pretty easy to navigate once we were in town. After landing at Midway, we hopped on the L to find our way to the hotel to drop our bags.
Next up, lunch! We walked a few blocks and hit up Giordano’s for classic Chicago-style pizza and it did not disappoint! By the time lunch was done, it was raining pretty good so we made a pitstop at the CVS nearby to buy ponchos that screamed “tourists” – I had checked the weather but failed to bring umbrellas so this would have to do!
We spent the rest of the afternoon wandering around Millennium Park, checking out The Bean and wandering up and down Michigan Avenue. We stopped by the hotel to rest a bit and warm up/dry off before walking a few blocks to dinner at Sweetwater Tavern before calling it a night.
Day 2 – Aquariums, Museums, Skating, and more!
We woke up well-rested and ready to tackle this jam-packed day. We grabbed breakfast at Wildberry to fuel up before making our way to Shedd Aquarium.
Side note: if you’re hitting several of the big touristy spots during your visit, check out the Chicago CityPass to see if it’ll save you money on admissions. For one price, you can get into 5 different hot-spots throughout town. If we had more time, I definitely would have gone this route!
We spent the rest of the morning wandering through Shedd before walking about 1.5 miles to Portillo’s for some Chicago dogs. We took our time eating and then decided to walk back towards Shedd to check out the Field Museum. I remember visiting when I was a kid and it was just as cool this time around. You could literally spend all day here. Don’t forget to visit SUE during your visit, too!
After spending a couple of hours at the museum, we walked back to our hotel for a little rest and to get cleaned up for dinner. One of the nice perks of traveling with a kid that’s a little older is being able to leave her in the hotel room while we grab a drink downstairs in the lobby bar – so that’s what we did!
We decided to treat ourselves to a nice Italian dinner at Rosetta (the rigatoni alla vodka and the mile high chocolate cake were sooooo good!) before ice skating through downtown at the Ribbon in Maggie Daley Park.
Ice skating with the Chicago skyline in the backdrop was probably one of my favorite parts of the trip. It was a really nice night, not too cold or anything, which made it so enjoyable!
Safe to say we were exhausted after this long day so after skating, we called it a night.
Day 3 – 360 Degree Views + Shopping
On our last morning in the city, we got packed up and checked our bags in the hotel lobby. Our flight wasn’t until the evening so we had plans to explore a bit before coming back to grab them before heading to the airport. Once those were situated, we grabbed bagels and coffee (I cannot remember for the life of me where but I do know they were delish!)
Next, we headed towards the iconic Magnificent Mile and the John Hancock building to check out panoramic views of Chicago – from 94 floors up!
Gracyn has a slight fear of heights so it was touch and go for a bit but she ended up putting on a brave face and catching some looks! It was a neat experience for sure!
We spent the next couple of hours wandering around the shopping district and admiring the designer stores from a distance. We made it a point to check out the American Girl store and the indoor shopping mall before stopping for a snack at the Nutella Cafe.
Just a heads up: your child will want the personalized container of Nutella and TSA will confiscate it when you forget about it in our carry-on luggage. 🤦♀️
By now it was time to grab our bags and find a place to relax for a bit – there was a Chiefs game starting soon and we had enough time to at least watch the first half before catching a train to the airport. There was a bar & grill near our hotel (again, can’t remember the name!) so we parked it there.
Wrapping Up 3 Days in Chicago
There is a ton to do in the city and I can’t wait to be back. Here’s some other things I had on my list of potential activities (something to keep in mind for our next visit):
- Navy Pier
- Lincoln Park Zoo and/or Brookfield Zoo
- Lincoln Park Conservatory and/or Garfield Park Conservatory
- Museum of Science & Industry
- Planetarium
- Museum of Ice Cream
- Sloomoo Slime Museum
- Lake Michigan lakefront, beaches, and swimming
- Skydeck Chicago
- Boat Cruise
- Sporting Events – Cubs, White Socks, Bulls, Bears, Sky – so many options!
- Art Institute
While it was a quick trip, we managed to pack it full and had the best time celebrating our girl. Like I mentioned above, we had never done something like this with any of our kiddos and it was such a special trip. We left exhausted but happy!
Looking for more family-friendly trip ideas? Check out all of our Travel By Oakley posts here!
