Kennedi Dale

The Perfect Chicago Vacation

Kennedi Dale
The Perfect Chicago Vacation

The Perfect Chicago Vacation


Chicago is easily my favorite city in the US. Maybe in the world. You don’t understand how much I love this city. There are so many must sees, must dos, and must eats. I’m going to give you the sight-seeing, food-eating breakdown, the Blissfully Blonde way. 


Millenium Park 


201 East Randolph Street

Chicago, IL 60601

At the corner of Michigan Avenue & Columbus Avenue

Here you will find the famous Bean! Here I am at the Bean my last few visits to this amazing city. If you go to Chicago in the winter time, they also have a cute little ice-skating rink set up right in front of the Bean. 


At this amazing park, there are also these Giant Faces on these giant screen structures. They are so neat, and if you catch them at the right time, they might even wink at you!


The Amphitheater at this park is an amazing sight to see. The architecture of this amphitheater makes the acoustics better than any I have ever heard before. 


The Fun Playground, I like to call it, is pretty much for children and adults. I’m twenty years old and I still play on it every time I go back. They have the coolest playsets for the kids, (and adults!) and little art pieces scattered throughout the play area. This is an awesome place to take your kiddos, or yourselves!


During the winter, they also have ANOTHER ice-skating rink just up the hill from the playground that is SO fun. It is called Maggie Daley Ice Skating Ribbon. It is an outdoor rink, in the shape of a figure eight, with some ends going uphill, and some going downhill. I think I once spent 4 hours here. Admission to the rink is free! Skate rentals are also $13 per person Monday- Thursday, and $15 on the weekends and Holidays. Check them out here.


Art Institute of Chicago


I am NOT a big art person. At all. Despite my indifference to art, I spent a few hours at the Art Institute and I adored my time there. I saw so many cool exhibits that combined history with art, something that I have come to love. They also had these amazing interactive exhibits that made me gain a newfound love and appreciation or art. Learn about the museum and purchase your tickets here


Chicago’s Magnificent Mile


If you are an adventurous shopaholic, THIS is the place for you. A mile of huge department stores, boutiques, five-star restaurants, and amazing hotels. I have stayed in a hotel on Magnificent Mile twice and loved it. You are in the middle of the hustle and bustle of the city life. This is definitely the perfect place to people watch. 


John Hancock Tower (360 Chicago Observation Deck)


The Hancock Tower, now the 360 Chicago Observation Deck, is one of the coolest places in the city. You can walk around the whole floor and see the views of this amazing city. They also have an attraction called the Tilt, which is CRAZY. I did not do the Tilt, I will never do the Tilt, but you definitely should. You step out on a piece of glass, hold onto these metal bars, and they tilt you out over the city. It is probably one of the most thrilling things you could do in the city. Buy your tickets here.


Willis (Sears) Tower Sky Deck


The Sky Deck Chicago at Willis Tower is my favorite attraction in the city. I think it’s a bit cooler and safer than the Tilt, so if you’re a scaredy cat like me, this is for you (even if you’re not scared!). The views from this tower are a little different than from the 360 Chicago Observation Deck because it is a few blocks away. I will never go to Chicago without going to the Sky Deck. Buy your tickets here


Tastebud Tours


$55 to walk around the city, go sight-seeing, and try some amazing food? One thousand percent worth it. I will do this again and again every time I’m in Chicago because it is so much fun. I learn something new and try something new every time I’m there. Purchase your tour here!


I hope my Perfect Chicago Vacation Guide helps you on your next trip! Send me a message and some pictures with everything you did!