On a sunny day, getting outside in late June in Chicago is pretty magical. We both love to walk or rent Divvy bikes to make our way along the Lakefront trail, or along the RiverWalk and grab a drink at the city winery. You can also take a Water Taxi or an Architectural Boat Tour on the river. If you've never seen them before, go check out Cloud Gate (the bean) and Buckingham Fountain and walk around the parks! Lincoln Park Zoo is also free and outdoors, and if you're in the area be sure to stop by the Alfred Caldwell Lily Pool, it's a Kulp family favorite.
We also love going to the Lincoln Park Conservatory, just be sure to get a reservation in advance, but it's otherwise free. Also free is the Chicago Cultural Center, which is beautiful. Our favorite museum by far is the Museum of Science and Industry, especially the U-505 tour. The Field Museum, Art Institute, Shedd Aquarium, and Adler Planetarium are all downtown and very worth the visit as well.
The Cubs will be playing at Wrigley Field all week, so there are plenty of opportunities to catch a game. If you're coming into town early and have a free evening, we also highly recommend checking out the Chicago Magic Lounge, or going to Old Town for a show at Second City!