We just returned from a whirlwind trip to the Midwest, visiting three destinations in five nights. It wasn’t exactly a slow-paced vacation, but we managed to make the most of our time.
Here’s the breakdown of our itinerary…it would make a great starting point for those wanting to visit Missouri and Illinois:
Day 1: Arrive in St. Louis. Grab a late-night snack.
Day 2: Explore Faust Park and the Butterfly House. Drive to the Lake of the Ozarks, with a stop in Columbia for pizza at Shakespeare’s. Arrive at the Lake in the evening and enjoy a moonlit boat ride.
Day 3: Don some sunscreen and hit the water for jet-skiing, swimming, and other lake activities during the day. Play a round of mini-golf or race around the go-kart track in the evening.
Day 4: Start the day with an all-you-can-eat breakfast at Kay’s Restaurant. Then hit the road to Chicago, which is about a seven-hour drive from Osage Beach. Arrive in Chicago, and grab a snack and a glass of wine at the popular foodie-hangout The Purple Pig, located on The Magnificent Mile.
Day 5: Take a tour of Wrigley Field and learn all about the historic ballpark’s story. Enjoy lunch nearby in Wrigleyville. Then take a cab to Willis Tower (formerly Sears Tower) and enjoy the views. Have an early dinner at Harry Caray’s Steakhouse.
Day 6: Before heading out of town, visit one of Chicago’s iconic museums. We chose the Field Museum, based on our daughter’s love of dinosaurs and other prehistoric animals.
As you can see, we managed to have a lot of fun (and learn quite a bit along the way) in a short amount of time. We would have loved to spend more time in all three destinations, but vacations can’t last forever. I’ll be writing more about several of these adventures in the coming week or two. I hope you’ll stop by.


Looking forward to the details, especially the Wrigley Field part.
The Wrigley tour was definitely the highlight of our trip! I’ll be writing more about it this week…
sounds like a great trip! how did you score a tour of the field?
Wrigley Field tours can be booked online. They have game-day tours, which are somewhat limited because there are parts of the ballpark that can’t be accessed on game days. We did a non-game day tour, which is more extensive. It was so fun!