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With less than 24 hours in the city of Chicago before heading to Indiana for our niece’s birthday party, we nailed the itinerary! If you find yourself in the Windy City with just a little time to spare but a lot of interest in seeing the sights, here’s the plan to catch the best of Chicago…
12:00 – Lunch at The Purple Pig
2:00 – Architectural Boat Tour
3:30/4 – Walk to Millenial Park & “The Bean” (Cloud Gate)
5:30/6 – Dinner at Cindy’s
7:30 – Drinks & Lawn Games at Park Grill
We drove from the airport straight to The Purple Pig (James Beard winner and delicious sharing plate restaurant full of unique dishes and fresh fare). The tuna tartar and the shrimp and avocado salad were table favorites!
From there the Architectural boat tour was just a block away and the perfect place to see all of the city’s interesting architecture and learn about the unique history of the city in a 90 minute span with minimal walking which is especially helpful if you have small kids! Sit on the bottom of the boat in the very front. There’s limited seating here so it feels like you have the boat to yourself and you’ll have the best views and a little more shade than if you sit up top. We missed this opportunity but try Wendella tour since it’s the original.
From there we walked (about 1/2 a mile and our kids made it, no complaints!) to Millenium Park to see The Bean (Cloud Gate). We walked around the park, caught a bit of a concert and then headed to Cindy’s, a quintessential rooftop restaurant overlooking the park. Highly recommend but make sure to reserve a table in advance.
After dinner the kids needed to get some energy out and we ended up at Park Grill’s beer garden for a drink to cap off the trip. We played some yard games before we headed out of the city and into Indiana for the remainder of our midwest trip.
What are your favorite or best recommendations for Chicago? Comment them below!
For a quick trip like this one, classic pieces are key! I’m loving this striped t-shirt, pullover sweater, wide leg white jeans, and tasteful sneakers. For more outfit inspo, check out the blog or my LTK!