Chicago has never been more than a half-day’s drive away from me, and I’ve been there many times. There is plenty to do, but it can be a challenge getting around by car (parking is terrible and very expensive) and none of the attractions are cheap, either. That being said, with a little research and planning Chicago can be a great weekend destination for all budgets!
Pre-baby at Shedd Aquarium with one of my best friends.
In 2014 I had a nice trip with a friend and 18-month-old daughter. We explored the Children’s Museum on Navy Pier, and let her loose in Jane Adams Memorial Park.
Enjoying Chicago outside of the Cheesecake Factory, in the children’s museum, and Adams Park
We returned again in 2016 in order to fly out of Chicago O’Hare International Airport (much cheaper for us to fly out from there rather than closer to home) and we literally only paid for parking for the entire day, thanks to my cooler full of food and awesome free activities like swimming on North Avenue beach and then walking to Lincoln Park Zoo, which is also free!
North Avenue Beach
Lincoln Park and the free Lincoln Park Zoo
Across the Never Sky 