Chicago in a Minute – Things to See and Do

Growing up there were only a few things that I knew about Chicago. 1) It is a really windy place. 2) Oprah 3) They are famous for their deep dish pizza and 4) The TV Show Perfect Strangers was set there. Don’t tell me you don’t know who Balki Bartokomous is…

Chicago was always in the back of my mind as a place that I wanted to visit sometime, but I wasn’t sure when. Up until this point I had only visited the O’Hare airport in transit to other destinations. Happily in June I finally got to visit the windy city as I was going to teach at the 4th Navigate Media Group BlogHouse and planning on staying around for a few days after to explore the city.

bloghouse chicago group photo 2 - Chicago in a Minute

The fun BlogHouse Chicago gang

The BlogHouse was held at the Villa D Citta B&B in the Lincoln Park neighbourhood of Chicago. Voted one of the Top 10 B&Bs in the US it was the perfect location for our four day three night blogging intensive.  Over the four days myself and other members of NMG taught our 14 selected applicants the best we knew about the ins and outs of blogging from how to optimize and make their sites better to teaching them the tricks to social media, helping them learn how to pitch trips and projects, giving them photography and video tips and so much more. It was definitely the best BlogHouse yet and wouldn’t of been possible without our partners FlipKey, Gogo, Goose Island and MegaBus.

chicago bloghouse electric boat group - Chicago in a Minute

Me during a BlogHouse outing as Captain on our cruise down the Chicago River

It was an intense few days and I was happy to have time to explore after it was all over as there is so much to see and do in Chicago. I actually didn’t get to stay long enough and now need to find an excuse to get back to Chicago again soon. I had to cut my trip short as I didn’t book my accommodation in advance and everything was sold out. Someday I will learn to stop doing this…

chicago bean cloud gate at millenium park - chicago in a minute

The Bean aka Cloud Gate. You need to wake up early to try to get a photo without a million people in front of it.

Aside from bumming a bed from friends for one night I spent my non-BlogHouse time in Chicago staying at the HI Chicago Hostel. An over 500 bed hostel smack dab in the middle of the loop in downtown Chicago. Just a couple blocks from Millennium Park and “the bean” this hostel truly was the best location to stay in the city. Bonus, breakfast is also included. UnBonus the “L” aka elevated train aka Chicago’s version of a subway runs above ground right next to the hostel and is extremely loud.

Cailin at Skydeck Chicago - Chicago in a Minute

Hanging out on the SkyDeck at the Willis Tower, hovering over the city 103 stories below

With only a few days to explore I tried to pack in as many awesome things into my few days in the city as possible. I took not one but two food tours. One with Chicago Food Planet was a nice overview of the food scene in the city and the other with Chicago Pizza Tours. We ate 8 different kinds of pizza in three hours. It was glorious, read more about it HERE. I went all the way to the top of the Willis Tower (Sears Tower) and I stood out on the Skydeck with its glass bottom 103 stories high in the air. I explored the Millennium Park, rode the “L” around the city, and went to see a comedy show at the famous Second City.

cailin and a chicago dog hotdog - chicago in a minute

Mmmm tasty Chicago Dog and I don’t even like mustard!

However I didn’t stop there. I also went to the Lincoln Park Zoo, but got there too late and missed the rhinos. Boo. I stopped by Wrigley Field for some obligatory photos. I visited the Navy Pier and paid way too much money to ride a ferris wheel that only got me around one spin. I even tasted a crazy Chicago Dog which is a hotdog topped with onions, tomatoes, hot peppers, celery salt, pickles and LOTS of mustard (no ketchup allowed).

Even though I did all of this in just three days there are still so many things that I missed and hope that I can get back there again soon to do. Things I missed out on are going to Chinatown, going to the top of the John Hancock Tower, taking more food and pizza tours including the night time prohibition drinking tour, visiting the beaches, eating at the most recommended place in the city “Hot Doug’s” (sadly I hear it is closing in the fall of 2014), going to the museums and art galleries, riding a Divvy bike and so much more.

To see some highlights of what I did manage to see and do in Chicago check out my newest video “Chicago in a Minute“. This video highlights some of the best things to see and do in Chicago in just a minute.

What did I miss? Is there anything else that you would recommend people see and do in Chicago? Tell us in the comments below.

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  • Reply
    August 3, 2014 at 11:03 pm

    Chicago is such an epic city …. deep dish pizza, skyscrapers and a chrome bean … how can you lose? :)

  • Reply
    July 12, 2014 at 4:59 am

    So glad you could finally experience some of what Chicago has to offer! It’s an amazing city right? I hope you’ll forever have fond memories of being our Captain hahaha :)

    • Reply
      July 12, 2014 at 7:54 pm

      Thanks Beth! I will for sure! I can’t wait to visit again :)

  • Reply
    July 11, 2014 at 2:31 pm

    I love this, especially the video! Haha your souvenir picks are fun too : ) I’m disappointed there wasn’t more boat footage though! Thanks for being such an inspiration for video, watching yours reminds me of how much of a difference it makes. Would love to have MORE sessions on video at BlogHouse II.

    • Reply
      July 12, 2014 at 7:54 pm

      Thanks Kristin! I will keep that in mind for the next BH :)

  • Reply
    Chanel | Cultural Xplorer
    July 9, 2014 at 3:56 pm

    You’re video was a lot of fun and captured everything in a minute! Nice :D I also like the word ‘unbonus’ haha

    • Reply
      July 9, 2014 at 9:11 pm

      haha thanks Chanel! I thought “unbound” fit the situation perfectly haha

  • Reply
    Candice @ The Let's Go Ladies
    July 9, 2014 at 3:53 pm

    Oh god, that picture of you with the glass floor almost made me pass out a little. Good on you for doing it. I’ve been to two buildings with glass bottom floors, and both times I wasn’t able to step both feet onto it. One foot was okay, but two was just NOT DONE. Also, Chicago looks so awesome, I need to go there asap.

    • Reply
      July 9, 2014 at 9:17 pm

      Candice I’m surprised at how many people are afraid of the glass bottom floors, I didn’t even think twice about it! haha There was a little kid there and his mom picked him up and forced him on it for a family photo haha.
      I was probably on it for 10 minutes!
      And yes you do need to get to Chicago asap :)

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