We’re back from our whirlwind adventure to Chicago and managed to all survive the trip! We were gone five days, but with a full day of driving there and a full day back, we had to cram lots of fun into only three days.
Packing for five people is intense!
We really approached the drive with no expectations. The drive from Toronto to Chicago is eight hours – not including breaks or the border. I wasn’t expecting us to roll into town until way after the kids’ bedtime, but after leaving at 7:30 AM and gaining an hour with the time change, we made it there in time for dinner.
Our walk on the beach
Our first day, Tuesday, was pretty relaxed as we were all tired from the long drive and there was a big storm that morning in Chicago. We enjoyed some time at Target (sooo much better in America!) and when the skies cleared and the sun came out again, we walked along the beach that was all of five minutes from the hotel.
Meeting baby C!
That night, we finally got to meet Miss C who gave her parents a hard time with her NICU staycation, but looked lovely and despite how big she is for a newborn, seemed so little! She didn’t even make a peep while our three children ensured everyone paid attention to them.
A little break!
Buds was pretty quick to notice that Chicago has a plethora of buses and his only request was to go on a double decker and sit on the top, and we were happy to oblige! The bus took us all over the city and it was a beautiful day. The view of the skyline from Museum Campus is unbelievable.
Buds on a bus!
B loved seeing all the buses!
After the morning spent on a bus, and a massive yet delicious lunch at The Cheesecake Factory, the kids all collapsed in exhaustion for the afternoon. Once they were finally up, we headed for pizza and pasta with some more of our favourite Chicagoans.
Dinner!
Jas and B enjoy some pizza
B walks back to the hotel with his new friend!
Our last day was spent back with Miss C and her awesome parents at Lincoln Park Zoo. If you haven’t been and find yourself in Chicago, it should be a must-see! It’s small but FREE and gorgeous, tucked right in the city near the lake. B was delighted to find a little train near the entrance, and went on twice.
Best view in the house
Fishies!
Riding the train
To end our awesome trip filled with sun, friends, and laughter, we headed to one of our favourite joints, Ditka’s. Jas of course requested the Packers section and I had meatloaf that could quite easily feed a family of 8.
Mama and Ella at Ditka's
Famjam!
You would think that traveling with a toddler and five month old twins would be stressful and crazy, but aside from all the stuff we had to bring, it was fairly relaxed. We didn’t plan anything but we all had fun and the unexpected bus tour was so much fun. We’re thinking of taking a road trip every year and next year we’re thinking Boston!
The kids all tuckered out!
Adventures With Multiples 
Where do get the money to travel so much with three little ones? You obviously don’t work, and I know that myself for one can’t afford such things. I also disagree with your comment about Target being better in the States, the only thing that may be better is the prices, Canada is a much more beautiful place in my opinion. Canadian and proud.
I, too, am a proud Canadian. Unfortunately, the majority of the stores we shop at in Canada are American or owned by American companies. I was initially excited about Target coming here but they fell flat, in my opinion. I am currently on maternity leave and our trip was affordable as we drove and I found a great deal on Groupon for the hotel. We really believe that the experiences of being together as a family and enjoying new adventures are worth other sacrifices.