Honestly, I’ve always thought this–Chicago is one of the cities that makes me proud to be an American. It’s pretty & clean, the food is good and the people are happy & welcoming. What’s not to love?

Thanks to my boyfriend’s awesome family, I got to pull a Ferris Bueller and adventure around the city as a tourist the second I hopped off a plane from Asia.

Here’s what we did:

Skydeck Chicago Observatory at Willis Tower, or 360 Chicago Observatory at John Hancock Building

  • So there are two options for stellar views of the city: the Willis Tower or John Hancock Building
    • Perks:

The Willis Tower:

  • the infamous clear bottom ledges
  • 104th floor
  • $24 admission
  • Address: 233 S Wacker Drive

The John Hancock Building

  • the 360 was much less crowded and had larger, floor to ceiling windows
  • 94th floor
  • $20 admission
  • There was also a bar there and many events. I personally preferred the view at the John Hancock, but it doesn’t hurt to head to both.
  • Address: 875 North Michigan Avenue.
  • Millennium Park
    • We went to the iconic Millennium park to see the bean and enjoy the beautiful weather! So gorgeous & obviously a must do. I never really understood the hype of the bean, but by now, it’s become an icon to the city so it does not hurt to stop by!
    • Address: 201 E Randolph St.
  • Architectural River Cruise
    • This is voted America’s best tour on TripAdvisor and I was a little hesistant it was worth the $35 for the 90 minute tour, but I learned very quickly soo much about the city and Architecture in general. It sounds dramatic, but I literally look at building differently now.
    • Chicago grew after the Great Fire from a small settlement into one of the world’s largest cities in less than 100 years. The decades of the 1900s were all so unique in architectural style and that’s what they explained along the turn. The sun reflects off the water and the buildings, which was super neat. We went right before sunset and it was perfect timing.
    • Find the info here.
  • Cubs Game at Wrigley Field
    • As soon as we hopped off the plane, this was our first activity. There’s been a long time loyalty for  the Cubs in Chicago, but especially after ending their 108-year World Series championship drought. You’ve gotta go to a game. It’s not overrated. I’ve only got three words for you guys: Go. Cubs. Go.

I wish I had a full week in this awesome place! The food, the people, the pizza, the culture, the experiences: Chicago’s got a great vibe. Everyone should go when they get a chance. A special thank you to J’s family for all they did for me during my time in Illinois.

Hope you enjoyed reading this! I’ll definitely be back to this great American city, but these are a few one day must dos. Happy traveling! XOXO Alex