What Should I do in Chicago?

I’m obsessed with the idea of travelling but hardly make time to do it on my own, unless someone else commits to going with me. I’ve always wanted to travel alone, but when I sit down and try to solidify plans, it’s really hard for me to commit for fear that something else will come up at the same time. What I’m really saying here is that I have crippling FOMO, which is embarrassing but whatever. I just don’t want to miss birthdays and other miscellaneous celebrations and gatherings! So, when Southwest had their semi-annual sale last month, I stopped overthinking and started planning. I booked a trip to Chicago at the beginning of December (less than a week after I get back from a cruise to Mexico. YOLO) and a trip to San Francisco at the beginning of January (the week before I start weekly business trips out of state. Again, YOLO). I’m so excited to go to Chicago, I’ve been Googling the must-do tourist things but I don’t want to miss anything so I thought I’d also ask my readers. Below I’ve listed all of the suggestions I’ve heard of places to go and events to attend between 12/9-12/12. Am I missing anything? Have I included something that actually kind of sucks? I’m staying at the HI Chicago Hostel in The Loop, what’s the best way to get around from there? I know there are so many public transportation options but I feel like I’ve waited too long and don’t have enough time to learn how to make them work for me!

TL;DR: I need all the help I can get. Tell me what to do in Chicago and how to do it (and how to get to it).

  • Buckingham Fountain
    •  This was suggested to me, but I just read that it only operates April-October. Did I miss my chance? Haaaaaaalp.
  • Grant Park
    • This seems so general. Are there specific things in Grant Park? Or is it just an abnormally cool park?
  • State Street shopping
  • Art Institute of Chicago
  • Museum of Contemporary Art
  • Museum of Science and Industry
  • The Bean
    • This is one that I’ve read a lot of people say not to waste your time on. I love tourist-ing, so I’m ignoring them all.

Special events that I’ll be in town for:

  • 21st Annual Christkindlmarket
  • ZooLights
  • Winter Wonderfest
  • B96 Pepsi Jingle Bash
    • This is kind of a last resort. But also Britney!!! How are tickets so cheap?!?!
  • Morton Arboretum Holiday Lights
  • White Christmas (the musical)
  • Chicago Art Girls Holiday Pop-Up Shop
  • Dose Market


That’s it! What am I missing?

Thanks in advance!




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